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Holiday Rentals in Bend

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    Travellers to Bend are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Enjoy the luxury of a private, gated golf community in this beautifully-furnished townhome. Villa #6 is a two-bedroom, two-bath townhouse located in the quiet community of Broken Top. Enjoy beautiful views of the 18th Fairway of the privately-operated Broken Top Golf Course from the living room and... View all property information
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    Bend, Central Oregon 97702
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located in the exclusive Broken Top Club, Villa #5 is a convenient, yet luxurious, location on Bend's Westside. This two-bedroom condo features two King Master Bedrooms, a hot tub on the large deck and a gas fireplace. Villa #5 is only minutes from shopping and dining in both Downtown Bend and the... View all property information
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    Bend, Central Oregon 97702
    1 / 15
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    A vacation of your dreams, this first floor unit of the Pioneer Park Condos is well appointed with modern decor and fantastic amenities. Just north of downtown Bend and within walking distance to pioneer park, you'll never miss a thing! Enjoy access to the nearby covered pool and hot tub. A perfect... View all property information
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    Bend, Central Oregon 97701
    1 / 13
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Perfect location for the professional needing and extended stay in Bend, OR. This quiet 2 bedroom, 2 bath unit is fully equipped for the professional traveler. Complete kitchen and linen package. You only need to bring your clothes and personal items. Close to St Charles and the medical district... View all property information
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    Bend, Central Oregon 97701
    1 / 24
    3 of 5 bubbles (1) Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Situated comfortably on the first floor of the lovely Pioneer Park Condos, this full-sized unit has plenty of space for up to four guests. With the largest outdoor patios in the community, and gorgeous views of the park and common area gardens, this is the perfect space for friends or a few couples... View all property information
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    Bend, Central Oregon 97701
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    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Mountain Views
    • Central Heating
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    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Nestled in a forest, this tranquil home has a convenient location only 5 minutes from downtown. Close to ski resorts, Pilot Butte mountain, restaurants, three gorgeous parks, many trails, dog park, skate park, shopping, winter sports and everything the region offers. Kevin’s large house is an... View all property information
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    Bend, Central Oregon 97702
    1 / 29
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Perfect for a quick romantic weekend or a solo retreat to beautiful Bend, this studio will help you feel right at home in sunny Central Oregon! Located about a mile away from downtown Bend, and within walking distance of Pioneer Park for the morning or evening workout, this charming condo keeps you... View all property information
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    Bend, Central Oregon 97701
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    1 / 26
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This slick Skyliner condo is the perfect home base for exploring the Bend area with access to the Pioneer Park community pool and hot tub. Located about 20 miles from Mt. Bachelor and and close to downtown Bend, this home is in an ideal location for adventure - both urban and outdoor! Elegant... View all property information
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    Bend, Central Oregon 97701
    1 / 13
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The best way to enjoy your trip to Bend Oregon. The Pioneer Park Condominiums are located next to the beautiful Pioneer Park along the banks of the Deschutes River. With access to the river trail you will find hours of relaxing strolls with exciting views of the river on classic Central Oregon... View all property information
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    Bend, Central Oregon 97701
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
    • Mountain Views
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    The home is located in a quiet and peaceful setting, just minutes from all the great entertainment and restaurants to be found in downtown Bend. If you like great beer, you are in the right place. At last count, there were 31 micro breweries in town. Spring is a great time to be in the house.... View all property information
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    Bend, Central Oregon 97702
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Fantastic balcony overlooking the green space at the coveted Pioneer Park Condominiums. Moments from a trail that follows along the banks of the Deschutes River; follow it to the beautiful Pioneer Park. Only a few blocks away you can find music, food and unique shopping in downtown Bend. If you... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 36
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Hot Tub
    • Parking
    • DVD Player
    • Satellite TV
    • Waterfront
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This riverfront Bend home on the Deschutes River offers views of the water from the comfort of a private hot tub and sleek, stylish home interior. This home is within walking and biking distance of downtown Bend and the Old Mill District, making it a great rental for the urbanite in your group.... View all property information
    Location Information
    Bend, Central Oregon 97701
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    An open-concept living space, this unit is modern and cozy. This spunky one bedroom, two bathroom unit is upscale and cozy. The dark wood and black and white decor are pleasing and modern. Enjoy the rich leather couch and a reading chair facing a patio, equipped with a gas grill for outdoor... View all property information
    Location Information
    Bend, Central Oregon 97701
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
    • Balcony
    • Internet Access
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    • Air Conditioning
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    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Spacious enough for four lucky guests, this second-floor unit in the lovely Pioneer Park Condos makes a wonderful home away from home in the heart of Bend! Located just a mile away from downtown Bend, and about 22 miles away from Mt. Bachelor, this beautiful home is close to everything, including a... View all property information
    Location Information
    Bend, Central Oregon 97701
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    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • ?
    About this property
    Albany House Stay near beautiful Downtown Bend in this recently renovated, cozy cottage!  Albany is a well-furnished, three-bedroom, two-bath home located in a charming residential neighborhood only minutes from Downtown Bend and the Old Mill District. Albany features a Queen Bedroom and full... View all property information
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    Bend, Central Oregon 97702
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Smoking allowed
    • ?
    About this property
    Looking for a modern getaway convenient to both outdoor recreation as well as the comforts of town? Urban Roundabout is a newly built, northwest contemporary home within walking distance to Newport Market, local restaurants, coffee houses and bike shops. This state-of-the-art BRAND new home... View all property information
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    Bend, Central Oregon 97702
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    The best way to enjoy your trip to Bend Oregon. The Pioneer Park Condominiums are located next to the beautiful Pioneer Park along the banks of the Deschutes River. With access to the river trail you will find hours of relaxing strolls with exciting views of the river on classic Central Oregon... View all property information
    Location Information
    Bend, Central Oregon 97701
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Enjoy what Central Oregon has to offer in outdoor recreation with easy access to main arteries; walking distance to downtown restaurants, shopping, and entertainment and walk to local favorites like Pioneer Park and the Deschutes River trail. This unit is the perfect intimate get-a-way for any... View all property information
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    Bend, Central Oregon 97701
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Classic log cabin charm meets industrial vintage style. Quality natural fibers and stone are used to update this space into a cozy log cabin experience you will soon not forget. Whether listening to the wind in the pine trees or enjoying a warm real log fireplace, the feel of the big city will be... View all property information
    Location Information
    Bend, Central Oregon 97707
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Furnished 4 bed, 3.5 bath home. River view and deck. watch the river from the living room window. Large dining room seats 6. Eat-in kitchen with breakfast bar, dishwasher and microwave. Master bedroom has a river view from private deck. View all property information
    Location Information
    Bend, Central Oregon 97701
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Newer home on the West side of Bend, Private side yard with mature foliage. This two story home in classic west side neighborhood boasts recent furnishings, lots of natural light and easy access to the river, downtown, the Old Mill and Mt Bachelor! An open floor plan seamlessly melds the kitchen... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 15
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    The best way to enjoy your trip to Bend Oregon. The Pioneer Park Condominiums are located next to the beautiful Pioneer Park along the banks of the Deschutes River. With access to the river trail you will find hours of relaxing strolls with exciting views of the river on classic Central Oregon... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
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    About this property
    Really cute 1 bedroom unit on the NE side of town. Nice hardwood floors. Fenced yard in rear for a well behaved pet. Really cute patio area with outdoor seating. Kitchen has sink and good counter space. Stainless fridge and micro. Perfect place for someone seeking housing instead of paying for a... View all property information
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    Bend, Central Oregon 97701
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Patio
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    *Please note this is a Guest House attached to a separate main house on property that is owner occupied. Central Oregon is a recreational paradise, offering snowy mountains, sparkling rivers, alpine lakes, sagebrush plains and incredible views, not to mention over 300 days of annual sunshine.... View all property information
    Location Information
    Bend, Central Oregon 97701
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Modern decor and a central location make this Bend vacation rental an ideal getaway. A chic Wall Street Condo, Pioneer Park Condominiums offers luxury amenities to plan the perfect romantic getaway! This upscale unit is located in Pioneer Park Condos, a pleasant community right on Wall Street,... View all property information
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    Bend, Central Oregon 97701
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    This newly remodeled 1 bedroom/1 bath is ideally located close to St. Charles hospital, shops and restaurants. Perfect for long term stays. Professionally decorated, fully furnished and completely stocked. Complex has beautifully maintained green spaces, dog friendly stations, picnic areas and... View all property information
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    Bend, Central Oregon 97701
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    Perfect retreat for two in popular West Bend neighborhood. Relax in this cozy upstairs apartment after a day of exploring this growing Central Oregon town. A second story loft apartment with its own private entrance is waiting for you. It is just west of downtown, in a quiet neighborhood near... View all property information
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    Bend, Central Oregon 97701
    1 / 15
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    The best way to enjoy your trip to Bend Oregon. The Pioneer Park Condominiums are located next to the beautiful Pioneer Park along the banks of the Deschutes River. With access to the river trail you will find hours of relaxing strolls with exciting views of the river on classic Central Oregon... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This cute one bedroom fully contained apartment is adjacent to my home in a quiet safe neighborhood in SE Bend. It is easily accessible to Highway 97 and the Parkway, minutes to stores, pubs and 12-15 minutes drive to the Old Mill and downtown Bend. 45 Minutes to Mt Bachelor skiing! The unit is... View all property information
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    Bend, Central Oregon 97702
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    This newly remodeled 2 bedroom/1 bath is ideally located close to St. Charles hospital, shops and restaurants. Perfect for long term stays. Professionally decorated, fully furnished and completely stocked. Complex has beautifully maintained green spaces, dog friendly stations, picnic areas and... View all property information
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    Bend, Central Oregon 97701
    1 / 65
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Balcony
    • Internet Access
    • Grill
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Featuring a gourmet kitchen, bright and airy living spaces, a game room, multiple Jacuzzi tubs, and a well-appointed deck with a spectacular view of six Cascade peaks, you'll feel refreshed and invigorated when you and your family wake up in this beautiful custom home with 5,000 square feet of... View all property information
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    Bend, Central Oregon 97703
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    This newly remodeled 2 bedroom/1 bath is ideally located close to St. Charles hospital, shops and restaurants. Perfect for long term stays. Professionally decorated, fully furnished and completely stocked. Complex has beautifully maintained green spaces, dog friendly stations, picnic areas and... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    Minimum stay:2 nights Internet:Yes Pets considered:No Wheel chair accessible:N/A Located in Bend’s desirable Westside, 'Columbia Street Retreat' is walking distance to Drake Park, downtown, great dining, coffee shops and bakeries, gourmet grocery stores and many other conveniences. This clean and... View all property information
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    Bend, Central Oregon 97702
    1 / 18
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    As part of the beautiful collection of Pioneer Park condos, this stylish downtown Bend vacation rental is waiting to make your family or group of friends feel right at home in Central Oregon! This adorable unit is quiet, with great amenities including WiFi and cable. There is a small,... View all property information
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    Bend, Central Oregon 97701
    1 / 25
    4.5 of 5 bubbles (8) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Plan a snowy holiday in this one-bedroom home with a loft and luxury resort attractions at Mt. Bachelor Village. The inviting space is perfect for six guests (four adults) wishing to explore Oregon by river or mountain top! This condo is surrounded by nature. The Deschutes River Trail is outside... View all property information
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    Bend, Central Oregon 97702
    1 / 25
    3 of 5 bubbles (3) Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Sauna
    • Patio
    • Satellite TV
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    • Air Conditioning
    • Grill
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Explore Oregon's high desert in this chic condo with resort amenities and a central location in Bend! The modern space is the perfect hideaway for days spent outdoors or brewery hopping with friends. Wall Street Condo is located in Pioneer Park Condos, an inviting community near the Deschutes... View all property information
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    Bend, Central Oregon 97701
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • Balcony
    • Parking
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The go-to destination for dining, shopping, and entertainment, the Old Mill District is within walking distance of this 3BR/2BA Bend house. A mix of old and new, the district offers boutique shops, art galleries, restaurants, amphitheater, and even a fly fishing course. When the weather’s warm, try... View all property information
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    Bend, Central Oregon 97702
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • ?
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    About this property
    Beautiful Salmonberry is a newer 2 story home in Bend's lovely west side. Upstairs features 2 queen master suites, each with it's own full bathroom. Upstairs vaulted ceilings create space and light. The kitchen is fully stocked and beautifully appointed. Gas fireplace and large HDTV in the living... View all property information
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    Bend, Central Oregon 97702
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Grill
    • Mountain Views
    • Parking
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come enjoy Central Oregon while enjoying the authentic charm of this Old Mill home with mountain views perched above the Old Mill District. You're within biking distance to all the shops, restaurants and theater in the Old Mill District. There are three well appointed bedrooms and... View all property information
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    Bend, Central Oregon 97701
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Beautiful newly remodeled west side retreat for 2. 1 bedroom / 1 bath, fully stocked kitchen, washer and dryer, single car garage, deck with BBQ. Available for monthly rentals. All utilities, wi-fi internet, cable tv, trash service and maintenance included. View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Quiet townhome on the East Side of Bend. Close to St Charles and medical district, Costco, Safeway, Whole Foods, great shopping and restaurants. View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 29
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Grill
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    • Parking
    • Patio
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    We are new to TripAdvisor. Although we don't have any reviews yet on Tripadvisor, we are Superhosts on another site, with over 120 reviews with an overall rating of 4.9 out of 5 stars. What Guests Say: "We had a great experience at the Drake Park Cottage! The house is charming and perfect for two... View all property information
    Location Information
    Bend, Central Oregon 97703
    1 / 10
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    We are new to TripAdvisor. Although we don't have any reviews yet on Tripadvisor, we are Superhosts on another site, and this listing has received 137 reviews with an overall rating of 4.9 out of 5 stars. What Guests Say: "Stan and Jan were amazing, esay to communicate with. The studio was clean... View all property information
    Location Information
    Bend, Central Oregon 97703
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    We are new to TripAdvisor. Although we don't have any reviews yet on Tripadvisor, we are Superhosts on another site, and this listing has received 132 reviews with an overall rating of 4.5 out of 5 stars. What Guests Say: "Fantastic location, incredible accommodations located across the street... View all property information
    Location Information
    Bend, Central Oregon 97703
    1 / 17
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    We are new to TripAdvisor. Although we don't have any reviews yet on Tripadvisor, we are Superhosts on another site, and this listing has received 120 reviews with an overall rating of 4.9 out of 5 stars. What Guests Say: "We had a great experience at the Drake Park Cottage! The house is charming... View all property information
    Location Information
    Bend, Central Oregon 97703