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Holiday Rentals and Homes in Bend, OR

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    Travellers to Bend are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 26
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    West Bend Luxury 3 BR 3 Bath Townhome - The Bluffs neighborhood of the Old Mill District. Close to Downtown, Mt Bachelor & Deschutes. The Oasis is a 1,763 square-foot, luxury three-bedroom and three-bathroom townhome located in the Old Mill District on the trendy west side of Bend, Oregon.... View all property information
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    Bend, Central Oregon 97702
    1 / 9
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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! View all property information
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    Bend, Central Oregon 97702
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    3-5 night stay minimum on holidays- please note monthly option of $2000 per month- guest pays utilities on monthly rentals This is a wonderful 3 bedroom 2.5 bath home.luxurylivingbend is the internet location1900 square feet Vaulted CeilingsVIEWS of PILOT BUTTE in your front yard!Cathedral... View all property information
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    Bend, Central Oregon 97701
    1 / 33
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    About this property
    The Bond Street town home is a beautiful 3,200 sq. ft. brownstone "walk up" three bedroom, three and half bathroom town home with a private roof top terrace and breathtaking views of the Cascade Mountain Range located in the heart of the Old Mill District Quarter of downtown Bend, Oregon. Enter at... View all property information
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    Bend, Central Oregon 97702
    1 / 26
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Surrounded by National Forest, you can't get any closer to Mt. Bachelor, golf, and the Deschutes River! Our luxury three-bedroom/three-bathroom + loft (2500 square foot) townhome sleeps up to eight adults comfortably. Each bedroom has an attached bath with master bedrooms on the first and second... View all property information
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    Bend, Central Oregon 97702
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Bend, Central Oregon 97702
    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick 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... View all property information
    Location Information
    Bend, Central Oregon 97702
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    1 / 26
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Bend, Central Oregon 97701
    1 / 33
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    With resort-style amenities, gorgeous views of the Deschutes River from private balconies, and a private hot tub, this two-bedroom Mt. Bachelor vacation condo offers deluxe accommodations from which to experience Bend. Located in the Mt. Bachelor Village Resort, this retreat overlooks the stunning... View all property information
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    Bend, Central Oregon 97701
    1 / 39
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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
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    Bend, Central Oregon 97701
    1 / 25
    3.5 of 5 stars (2) Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    1 / 28
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This updated Bend vacation rental is ready to send you on your Central Oregon adventures in comfort and style. Enjoy all the city has to offer - this unit is just a few blocks from downtown near Drake Park. This condo has a surprisingly spacious living room, with shiny wood floors and plenty of... View all property information
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    Bend, Central Oregon 97701
    1 / 32
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 on a cup of freshly brewed coffee. On a clear day view the weather conditions on Mt. Bachelor directly from the upper... View all property information
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    Bend, Central Oregon 97702
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    About this property
    Our 3BR/3BA condo suite sleep up to 8 people, and is located directly across from 2 heated outdoor pools, 3 hot tubs, sauna, mini golf, and a small convenience shop. This beautiful family vacation resort is located near Mount Bachelor, a premier Oregon ski areas and a multitude of outdoor Oregon... View all property information
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    Bend, Central Oregon 97702
    1 / 41
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    If you're looking for a fantastic Bend, Oregon vacation rental, this lovely four-bedroom Craftsman-style house is about to become your new dream destination! A private hot tub, a large front porch, and vistas of trees as far as the eye can see are just a few of the wonderful things you're sure to... View all property information
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    Bend, Central Oregon 97701
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    River views, a private hot tub, and premium amenities combine to make this Mt. Bachelor getaway a must for those looking enjoy everything Oregon's great outdoors has to offer. Situated in the Mt. Bachelor Village Resort, and just a short walk from the Deschutes River, this unit provides the perfect... View all property information
    Location Information
    Bend, Central Oregon 97701
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    1 / 29
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Perfect for your group of up to eight guests, this Westside Bend vacation home offers a spacious retreat with three master suites! It's ideal for couples and friends traveling together in scenic Central Oregon. Just under three miles west of downtown, you can be gallery browsing and brewery hopping... View all property information
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    Bend, Central Oregon 97701
    1 / 13
    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Grill
    • Secure Parking
    • Mountain Views
    • Air Conditioning
    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Resort Overview WorldMark Bend – Seventh Mountain Resort is an idyllic playground for sports lovers and adventure seekers. For snow–seekers this resort is the closest lodging to Mt. Bachelor, Oregon's most celebrated ski and snowboard area, just 14 miles away. Just steps from your door of this... View all property information
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    Bend, Central Oregon 97702
    1 / 29
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • 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
    1 / 23
    4 of 5 stars (11) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Located in the Deschutes National Forest with southern exposure, you're bathed in Central Oregon light. A coffee maker and small fridge are in the room for your comfort. There's a cafe table by the window to sip your coffee and watch the world go by. A full bathroom with plenty of cushy towels. Use... View all property information
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    Bend, Central Oregon 97701
    1 / 18
    4.5 of 5 stars (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Explore Central Oregon year round in this charming Mt. Bachelor Ski Resort condo with luxury amenities and mountain views! Plan a family ski holiday or summertime escape with great friends in this comfortable unit. This Oregon high desert vacation rental offers resort access, including tennis... View all property information
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    Bend, Central Oregon 97702
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 31
    3.5 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Enjoy all that Downtown Bend has to offer within walking distance from this conveniently located duplex. The Old Mill District is also nearby with great shops and dining options. If you're lucky enough to be in Bend for the Fourth of July, you'll be able to watch the fireworks at Pilot Butte right... View all property information
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    Bend, Central Oregon 97701
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    BEND, OREGON. THE MOUNTAIN TOWN THAT HAS IT ALL.A warm, inviting mountain getaway with a cosmopolitan appeal is what you'll find when you arrive in the friendly town of Bend, Oregon. Majestic, snow-capped peaks adorn the high-desert skyline, making for some of the best weather in Oregon—think... View all property information
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    Bend, Central Oregon 97701
    1 / 28
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Garden
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    3 bedroom, 1 bath original Craftsman on historic Delaware Avenue Like a breath of fresh mountain air this house will take you away from the frantic pace of the modern world and back to a time when board games and homemade pies were a staple of the lazy weekend. The Homer house is one of Bend's... View all property information
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    Bend, Central Oregon 97701
    1 / 27
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Walk to all that Bend offers in it's charming downtown. A wall fireplace that is remote controlled, nice comfy and modern furnishings,stainless steel appliances. It is all here on a second story condo that offers two balconies one from the master bedroom and the other from the main . Two full... View all property information
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    Bend, Central Oregon 97703
    1 / 36
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • 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
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    Bend, Central Oregon 97701
    1 / 22
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Use the pool and tennis courts. Walk to Old Mill Shopping Center, fifteen minutes on foot, three minutes on wheels! Big bathroom off the bedroom. Fully stocked kitchen and it's a sunny, southern exposure, delight to cook in. A wall of windows offers the Descuhtes forest and views of it's animals... View all property information
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    Bend, Central Oregon 97702
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The perfect spot for an outdoor adventurer or a romantic getaway, this Bend vacation rental is a great place to curl up with your favorite someone, or simply relax after a long day on the trails. Hosting up to two vacationers, this studio vacation condo will have plenty of space for you spread out... View all property information
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    Bend, Central Oregon 97701
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    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... View all property information
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    Bend, Central Oregon 97701
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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+)... View all property information
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    Bend, Central Oregon 97701
    1 / 8
    4.5 of 5 stars (40) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Tuck away in this studio loft that is just a 5-minute walk from downtown! Bend's finest architects and artists had a hand in creating this inspiring loft for the author, who created several books here. Thus the name "Writer's Retreat.” A couple or small family will adore this bright, cheerful... View all property information
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    Bend, Central Oregon 97701
    1 / 29
    4.5 of 5 stars (21) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    The Bungalow Company designed this home in 2002 and it is only a stone's throw from downtown Bend, as well as parks, restaurants, wine bars, breweries, and boutiques. The first floor features a hardwood floor, 9 foot ceilings and an open living area. The bedrooms upstairs are spacious with tall... View all property information
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    Bend, Central Oregon 97701
    1 / 24
    3 of 5 stars (1) Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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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
    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Grill
    • Parking
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Next time you take a trip to Central Oregon, stay here at this lovely Bend vacation rental and have amazing access to all things Bend has to offer - great views, beautiful weather, and delicious food! Located just a block from downtown Bend, and close to Pioneer Park for jogs and dog walks. Upscale... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 32
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bend, Central Oregon 97702
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 27
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is a FAMILY home only and no gatherings or parties are tolerated. Guests will be asked to leave should they not adhere to this rule. It does not get any better then the Elgin Escape. It is also just two blocks away from the popular Galveston Avenue area with its fantastic bakeries, outdoor... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 27
    4 of 5 stars (10) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Satellite TV
    • Parking
    • Patio
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Downtown and acreage, sounds amazing because it is. Perched at the base of Awbrey Butte sits the one level home called Portlandia. Mid-century furniture continues the open feel in this big home. The numerous windows flood light in the whole house. A spacious and modern four bedroom home, with a... View all property information
    Location Information
    Bend, Central Oregon 97702
    1 / 22
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Walk to downtown! This two level home is located in the ideal spot for your vacation experience, close to everything! Farewell Bend is located right by the river, popular walking trails and parks, The Old Mill, Les Schwab Amphitheater, and downtown. Bring your tubes, mountain bikes or skis...... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • 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
    1 / 25
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Patio
    • Grill
    • Hot Tub
    • Internet Access
    • Parking
    Suitability
    • 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
    Location Information
    Bend, Central Oregon 97702
    1 / 28
    2 of 5 stars (1) Poor
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Hot Tub
    • Parking
    • Internet Access
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    If you're looking for an intimate setting for your next Central Oregon, check out this little Bend vacation rental with access to a nearby pool and hot tub. Only a mile from downtown Bend and within easy reach of Pioneer Park, this home is close to urban delights as well as outdoor options like Mt.... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 40
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Terrace
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is a FAMILY home only and no gatherings or parties are tolerated. Guests will be asked to leave should they not adhere to this rule. Welcome to "THE HIGH DESERT ARK" - This home has curved exterior walls resembling a ships hull! Insulated concrete form construction. Designer cherry wood... View all property information
    Location Information
    Bend, Central Oregon 97701
    1 / 17
    4 of 5 stars (5) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bend, Central Oregon 97702