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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.
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    3 Bedrooms, Sleeps 6Quick View
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    1 Bedroom, Sleeps 4Quick View
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    About this property
    Gorgeous home on 5 acres, quiet yet close to town. Beautiful northwest mountain views. Beautifully furnished. Luxury furnishings with granite countertops, fine cabinetry; and a modern, elegant decor. Extra large windows allow in the light and beauty of the natural surroundings. The living room is...
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Relax in luxury with sweeping views of the Cascades in this five-bedroom custom home. Five Peaks is one of our largest vacation homes, and is ideal for family reunions or a getaway for several couples. Most of the rooms face the Cascade Mountains, and offer views of the Three Sisters, Broken Top...
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    Bend, Central Oregon 97702
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    A premier location at the beautiful Pioneer Park Condominiums. Located moments from the river trail that meanders along the banks of the Deschutes. You can follow this trail through to beautiful Pioneer Park; and on to the downtown core to enjoy fine music, food and unique shopping. You may even...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Enjoy this Bend Oregon Vacation Home that offers Mountain Views! This Bend vacation rental is located in the middle of the West side of Bend, Oregon and minutes via bike to Bend's mountain biking epicenter, the Phil's Trail Head System. Bend has been rated #1 in the country for diverse single track...
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    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    16 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    About this property
    Easy access to everything in Bend. This home on The Bluffs in the Old Mill District is one block away from the bustling shops and restaurants, and is walking distance to the Les Schwab Amphitheater. Walk along the Deschutes River Trail that is only steps away. Or, just relax in the backyard and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 10Quick View
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    About this property
    The Trailhead sits in the perfect spot; positioned to view the Cascade Range, and walk your mountain bike across the street to Phil's Trail, thus the name of this awesome home! Century Drive is one half block from this home -- Get to Mt. Bachelor in 24 minutes, downtown and the Old Mill in four...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, Sleeps 4Quick 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...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    A very spacious and open apartment with a complete kitchen and bath that offers a shower/tub as well. A flat screen TV offering dish menu for your viewing. Open beam ceilings with three ceiling fans as well as A/C make your visit so comfortable. A super comfy bed and as well as a blow-up mattress...
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    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Excellent home for 2 couples or a family with two or three children. A newer house with tiled floor in the living room and dining room. Kitchen has open access to the living room keeping the cook with the company and family. Unless, of course, you prefer to grill outdoors on the propane BBQ...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, Sleeps 6Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    Smoking allowed
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    This three bedroom, two bath with reversed living offers living/kitchen spaces upstairs, a master suite with hot tub, 800 square foot deck for outdoor living, and perfect accommodations for a family or couples sharing a vacation. Enjoy easy access to the Sunriver Village plus all access passes and...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Relax into this comfortable 3 bedroom 2 bath home on the westside of Bend. Only one block from the river and a charming foot bridge across to downtown Bend's vibrant restaurants and shops. Only 4 blocks to 10 Barrel and Galveston St with easy access to Century Drive and .... the Mountain!! The...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Want a home that is close to it all -- this is your answer in fine form, the "River Farewell". The master bedroom is located on one side with an attached full bathroom. The other two bedrooms and guest bath are on the other side of the home. Located right in the middle is a delightful dining (6+)...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Reviews
    3 Bedrooms, Sleeps 9Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away on a private acre within the Deschutes National Forest, this home, completely remodeled in 2012, offers a seven-person hot tub, firepit, and barbecue, as well as plenty of indoor amenities to make it ideal for a group of up to nine guests. An ideal location in the serenity of Central...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home was built with your every comfort in mind. An open living area or the whole family to play in; TV, games, cooking and dining. Three master bedrooms. An open gas fire pit in the fenced back patio. A patio and dining table in the front porch as well. Plank flooring in the downstairs and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful new home on Bend's Eastside. Close to Old Mill District shopping and fine dining. Minutes to downtown and access to major arteries. Enjoy real Bend living in this lovely, well appointed, home. Granite countertops throughout. A bright gourmet kitchen has a fully equipped kitchen--complete...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bendgetaway is a privately owned 2 bed/2 bath loft condominium located within the Seventh Mountain Resort near the town of Bend in central Oregon. Central Oregon is known for it's nearly 300 days of sunshine per year!
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Comfortable and cozy "Mirror Pond" sits on the banks of the Deschutes River at Mirror Pond and Drake Park in the heart of downtown. It is located in one of the most picturesque locations in Bend. This home has a mountain cabin and cottage feel inside and outside. Relax on the backyard deck and...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    This is a gorgeous house, newly remodeled and beautifully furnished. Located one block from the river on the west side, it's a short, charming walk to the shops, galleries and eateries of Bend's vibrant downtown. The bakeries and breweries of the Galveston St corridor are a few blocks to the west....
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown. This newly remodeled condo is part of the Pioneer Park Condos that are located along the Deschutes River. This ground floor unit is perfectly situated. A lovely river trail follows the Deschutes...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 2Quick View
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    Cozy condo perfectly nestled in West Bend - three blocks to Newport Market and an easy walk from there to west side breweries and eateries. Close access to Mt Bachelor as well. This condo has everything you need for a fun and relaxing get away: comfortable furniture, a well equipped kitchen, high...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Bend, Central Oregon 97703
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    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...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, Sleeps 8Quick View
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    This spectacular, 2,300 square-foot home is a modern and peaceful retreat located on the banks of the Deschutes River. The Golden Zone has four bedrooms, three and-a-half bathrooms, and large common areas with beautiful views of the river, but no river access.  A large entry on the main floor leads...
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    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Located between Riverside and Riverfront 1 block from the river, this adorable 1 bedroom cottage has high ceilings and a paved off street parking spot right in front of your door. Recently built in June 2015, which means everything is up to code and in excellent condition. Tastefully furnished and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Situated on the back side of the Inn of the 7th Mountain Resort above the Deschutes River. The river and trail system are just a short walk into the forest. Mt. Bachelor ski area is just minutes away. This quiet, secluded condo is a peaceful paradise and an outdoor enthusiasts oasis. A small gem...
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    Bend, Central Oregon 97702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Escape to the country in this gorgeous luxury 1 bedroom town house apartment on Old Bend Redmond Highway. Located on the 2nd floor, newly built. Queen Bedroom, high vaulted ceilings, lots of light. An extra large deck for private sun bathing and star gazing. The kitchenette has all new appliances...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Historic Delaware is vintage Bend at it's best! Next to Downtown, it's a short charming walk to Bend's vibrant shops, restaurants, art galleries and breweries. Remodeled with high ceilings and gorgeous wood floors, the kitchen is beautifully appointed. A high fenced backyard ensures privacy while...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    Smoking allowed
    About this property
    Walk into Serenity on the Bluffs and look around- you'll find a treasure in each corner. Luxury chandeliers playing the light to show off treasures in alcoves and walls. Sleep in 600 thread-count sheets, that feel like silk; dry off from your showers with bamboo towels, then use the provided...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Central Heating
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    Smoking allowed
    About this property
    Nice home in south Bend, Oregon close to Old Mill District, Factory Outlet Mall, restaurants, and movies. The house has a jetted tub, and a dry sauna, fireplace, Jen-air range, laundry facilities, and about everything you need. Yard frequented by squirrels, blue jays, and sometimes deer. Just...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    This home has a view that will take your breath away. You'll feel the tension leave the moment you walk in the front door. Enjoy majestic sunrises in the mornings while sipping a cup of freshly brewed coffee. On a clear day view the weather conditions on Mt. Bachelor directly from the upper deck....
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautifully, updated home with so much light and space. A stone's throw from the Deschutes River and the river trail, this classic downtown house is perfect for a romantic getaway, or a small family vacation. Both the front yard and back yard are open with a nice lawn, making each a great place to...
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    Bend, Central Oregon 97701
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    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...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    A three bedroom and 2.5 bath in this newly built home five blocks from Wall street to place you in the core of Bend. Experience modern living in a design from America's pioneer of modern American homes, designed a century ago! An airy downstairs area; with the living room, kitchen and dining room...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Exquisite newer home with a floor plan to hold large groups. Two levels with the master bedroom on the main level and three additional bedrooms on the second level. All beds are queen beds. The master has a he/she sink set and a deep jacuzzi tub, as well as a walk in shower. There is an office...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 12Quick View
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    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 spacious house is...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Awbrey House Just a short walk from Downtown Bend, is this gorgeous award-winning, four-bedroom home. This well-appointed home, which is lauded for its fine craftsmanship, features a gourmet kitchen with a stainless appliances, including a Sub-Zero refrigerator and a Wolf six-burner gas range and...
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    Bend, Central Oregon 97701
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Hill Top is a deluxe four-bedroom home on the south side of Awbrey Butte, on Bend's west side. Located in a quiet hillside neighborhood about ten blocks from Downtown Bend, it is within walking distance or a short bike ride to the Deschutes River at Drake Park. This three-story, architectural home...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 7Quick View
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    Bend always has plenty of great activities to keep everyone in the family busy. Widgi Creek is located next to the Deschutes River and only 15 miles from Mount Bachelor. This is a beautiful area with one of the best golf courses in the Bend area. This townhouse offers everything needed to have a...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    1 Review
    1 Bedroom, Sleeps 3Quick View
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    Location, Location, Location! Bend Zen is located in the "Gold Zone" of downtown Bend situated between Bend's premier shopping, dining, and entertainment establishments;  and centralized access to the outdoor recreation that makes Bend famous.  Only blocks from Downtown, the idyllic Drake Park, the...
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    Bend, Central Oregon 97702
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Review
    3 Bedrooms, Sleeps 5Quick View
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    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...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    12 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Patio
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is perfect for the family reunion, ski clubs, golfing groups, quilting/knitting groups, church groups, any retreat! Or, just a large family! Downtown is less then 4 minutes away! Easy access to all golf courses and 20 minutes from Mt. Bachelor and the Cascade High Lakes. Sleeps up to 15 with...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
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    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...
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    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    McKinley House is a newer 2 story home in a quiet neighborhood. It's a short walk to the river trail, shops, restaurants and theaters of the Old Mill District. Les Schwab amphitheater is just on the other side of the Deschutes River, again within walking distance. Minutes from downtown and easy...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Canal view is a beautiful home located on the canal near the Old Mill District. This four-bedroom home features airy, open living spaces inside, and outside space with landscape lighting, a stone patio and natural gas fire pit. The gourmet kitchen features beautiful cabinets, granite countertops, a...
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    Location Information
    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 2Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Irving Cottage! This 1 Br, 1BA cottage has been recently remodeled with all new furnishings throughout! In a quiet private location that's a very short walk to Juniper Park and about 1/2 mile walk to downtown. There's a queen master bedroom, a fully stocked kitchen and a lovely living...
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    Location Information
    Bend, Central Oregon 97701
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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