50 Best Bend Vacation rentals on Holiday Lettings - Apartments

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497 Vacation rentals

10

Bend Vacation studio rental

Central Oregon / Bend

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Air conditioning
  • Pet friendly
Note: We are new to Tripadvisor so we don't have any reviews yet. However, on one of the other big booking sites we are Superhosts and have hundreds of 5 star reviews. Here's a couple of examples: Megan - March 2017 We stayed here for our 5th anniversary and it was pe …see more

from $75 / night

$525 / week

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Responds fast!
avg. 1 hour 30 minutes

from $75 / night

(7) Excellent 

23

Hotel apartment rental in Bend

Central Oregon / Bend

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Exceptional value @ Mt Bachelor Village Resort this upstairs unit (no elevator) with 2 REAL queen beds. No sofabeds here but there are 2 queen beds and an additional small roll-away single bed. This is a tastefully updated and exceptionally clean unit in a resort sett …see more

from $130 / night

$750 / week

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Responds fast!
avg. 3 hours 57 minutes

from $130 / night

(5) Very Good 

15

Condo rental in Bend

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
This place has it all, super convenient and accessible to all of the amenities you want when you visit Bend. A stone's throw from the Deschutes River and it's miles of walking trails, a 5 minute walk to downtown, quick access to the Bend Parkway, and adjacent to rest …see more

from $99 / night

$650 - $850 / week

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Responds fast!
avg. 2 hours 35 minutes

from $99 / night

(2) Very Good 

10

Home rental in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
*FALL/WINTER/SPRING SPECIAL* Normally $150 a night now $125 a night. 4 night minimum. Not available with any other specials or Thanksgiving weekend or Christmas Break or Spring Break. Beautiful, built in 2006, 1800+ SqFt., Luxury 3 Bedroom lodge style v …see more

from $165 / night

$990 - $1,230 / week

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Responds fast!
avg. 2 hours 17 minutes

from $165 / night

(12) Excellent 

10

Vacation home in Bend

Central Oregon / Bend

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Otterhouse is a riverside, two-story chalet-style home featuring an open floor plan with natural light and vaulted cedar ceilings. In addition to the living room, it has a spacious, warm library\loft as well as a large TV entertainment room. There is a master bedroom up …see more

from $195 / night

$1,200 - $1,520 / week

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Responds fast!
avg. 2 hours 52 minutes

from $195 / night

(60) Excellent 

Certificate of Excellence

27

Vacation cottage in Bend

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Secluded and quite 1 bedroom cottage just a 4 minute walk across Newport Ave bridge to numerous activities and businesses in downtown Bend. ~Immaculate, professionally decorated Cottage. ~Large Bathroom with deep tub, tiled walls and multiple shower heads. Tankless wat …see more

Certificate of Excellence

from $169 / night

$1,125 - $1,250 / week

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Responds fast!
avg. 2 hours 6 minutes

from $169 / night

11

Vacation home rental

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
A newly remodeled 2 bedroom, 1 bath apartment, ideally located on the East side of Bend. It is near St Charles hospital and the surrounding medical district. You will also find Costco, Safeway and Whole foods conveniently located just a few blocks away. Many of Bend's g …see more

from $63 / night

$441 / week

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from $63 / night

8

Bend Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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 c …see more

from $140 / night

$840 - $1,200 / week

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from $140 / night

(1) Excellent 

16

Bend Vacation home rental

Central Oregon / Bend

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
This home is located on the desirable, southwest side of Bend in the heart of best recreation activities that Oregon has to offer. Easy access puts Mt. Bachelor skiing, fly fishing on remote lakes, mtn. biking, rafting, kayaking or the Old Mill District & Factory Outlet …see more

from $250 / night

$1,750 - $2,730 / week

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Responds fast!
avg. 1 hour 51 minutes

from $250 / night

(10) Excellent 

18

Vacation home in Bend

Central Oregon / Bend

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
Private country setting with mountain views just 5 miles northwest of Bend. This 12 year old home sits on 20 acres of open juniper and pine forest, surrounded by other large, open tracks of land. The setting is lovely and private - like your own, private park with a h …see more

from $250 / night

$1,750 / week

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Responds fast!
avg. 3 hours 33 minutes

from $250 / night

28

Vacation home in Bend

Central Oregon / Bend

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
This beautiful home has undergone a major remodel and was recently completed in the Spring of 2015. The house features a comfortable open style with panoramic windows and fabulous views of the Big Deschutes River. There is access to one of our two large decks from the l …see more

from $275 / night

$1,925 / week

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Responds fast!
avg. 1 hour 51 minutes

from $275 / night

50

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Get ready to live like a local in this gorgeous Deschutes Landing townhome with a lovely interior and great views! Located in the middle of Bend's historic Old Mill District, enjoy Bend from its very heart and leave your worries behind you. Close to everything, with a …see more

from $158 / night

$1,106 / week

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from $158 / night

14

Home rental in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Newer home in Old Mill District with back yard trail down to the river. Private backyard with mature foliage. This one story home in Elkhorn Estates boasts high vaulted ceilings, lots of natural light and easy access to the river, downtown, the Old Mill and Mt Bachelor! …see more

from $195 / night

$1,200 - $1,800 / week

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from $195 / night

23

Bend ski condo to rent.

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ski
  • Child friendly
  • Air conditioning
Available All of June 2017. Call for Month Special! Great getaway spot in the heart of Bend and close to all outdoor activities Skiing, Golf, River Rafting, Hiking and more. Front Second Floor Corner Unit with the Brickhouse Restaurant downstairs. In the heart of Do …see more

from $215 / night

$1,500 / week

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from $215 / night

(1) Excellent 

26

Vacation home in Bend

Central Oregon / Bend

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
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 f …see more

from $150 / night

$900 / week

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from $150 / night

15

Vacation home in Bend

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
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 restaurants of Bend's vibrant downtown. This home has a beautifully furnished King master bedr …see more

from $210 / night

$1,200 - $1,700 / week

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from $210 / night

15

Home rental in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
Great family home located in a quiet West side neighborhood. This home has lots of light and lots of room with 3 bedrooms and 2.5 bathrooms and extra kid friendly sleeping options in a loft. The well appointed kitchen has stainless steel appliances and is fully stocked …see more

from $275 / night

$1,600 - $2,250 / week

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from $275 / night

15

Bend Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Excellent home for a large group. 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. Master bedro …see more

from $150 / night

$800 - $1,300 / week

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from $150 / night

(7) Very Good 

36

Apartment rental in Bend with tennis court

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
Located on Bend's westside, a short walk along the Deschutes to the Old Mill district and off the Cascade lakes road to Mt.Bachelor, this cozy, recently upgraded condo in Mount Bachelor Village is a convenient base for any recreation or vacation plans. Features a full …see more

from $150 / night

$900 / week

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from $150 / night

(3) Very Good 

14

Vacation condo with shared pool in Bend

Central Oregon / Bend

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful family vacation resort is located near Mount Bachelor, a premier Oregon ski areas and a multitude of outdoor Oregon activities, including golf, rafting, hiking, and rock climbing. Seventh Mountain Resort offers unparalleled views of the Deschutes Nationa …see more

from $109 / night

$763 / week

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Responds fast!
avg. 58 minutes

from $109 / night

13

Vacation home in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
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 se …see more

from $210 / night

$1,300 - $1,900 / week

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from $210 / night

14

Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Located in Bend’s Historic Westside, walking distance to beautiful Drake Park and downtown with its great dining, coffee shops, bakeries, gourmet grocery stores and many other conveniences. This newly-remodeled, clean and spacious, one bedroom house sleeps up to four pe …see more

from $130 / night

$775 - $1,200 / week

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from $130 / night

10

Bend Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
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 …see more

from $90 / night

$585 - $1,200 / week

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from $90 / night

12

Bend Vacation home rental

Central Oregon / Bend

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
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 kitchen …see more

from $125 / night

$800 - $1,200 / week

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from $125 / night

(5) Excellent 

42

Vacation condo in Bend

Central Oregon / Bend

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in beautiful Mount Bachelor Village offering spectacular views of downtown Bend & Old Mill District. This Condo House is 2.0 miles from downtown Bend and 20 miles from the slopes of Mount Bachelor Ski Resort. Nearby activities include downhill & cross-count …see more

from $150 / night

$1,000 - $1,175 / week

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from $150 / night

(8) Excellent 

35

Vacation home in Bend

Central Oregon / Bend

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
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 …see more

from $112 / night

$784 / week

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from $112 / night

(3) Very Good 

22

Vacation home rental

Central Oregon / Bend

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Enjoy the comfort and serenity waiting for you at this peaceful home with views to the Big Deschutes River. Watch ducks stirring the water or a heron standing nearby. Listen to geese pierce the calm as you absorb the tranquil beauty of this natural setting. With easy ac …see more

from $195 / night

$1,365 / week

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Responds fast!
avg. 2 hours 12 minutes

from $195 / night

14

Vacation home in Bend

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown! This condo is part of the Pioneer Park Condos that are located along the Deschutes River. This top floor unit is perfectly situated. A lovely river trail follows the D …see more

from $90 / night

$585 - $1,200 / week

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from $90 / night

(1) Excellent 

12

Bend Vacation home rental

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Cute and cozy cottage on the west side of Bend. A short stroll to First Street Rapids foot bridge and the river trail. 10 minute walk to downtown Bend with an assortment of restaurants, night life, and activities throughout the year. Convenient access to the parkway for …see more

from $150 / night

$1,050 / week

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from $150 / night

13

Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Available as a monthly rental, this beautiful 3 bed/2.5 bath home has high ceilings with sky lights for great lighting throughout the grand entrance. Enjoy sitting outdoors with plenty of seating around the fireplace and bbq. This home has a spacious office room on the …see more

from $93 / night

$651 / week

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from $93 / night

(2) Excellent 

21

Vacation condo with golf nearby in Bend

Central Oregon / Bend

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very clean, light and comfortable, well furnished one bedroom two full baths/shower/tub. Sleeps 4 very comfortably. Includes all utilities, wifi, basic cable, land line and use of all amenities. Fireplace ( presto log only), balcony with Deschutes Forest views and of …see more

from $165 / night

$1,055 - $1,250 / week

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Responds fast!
avg. 26 minutes

from $165 / night

8

Vacation home in Bend

Central Oregon / Bend

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Escape to the country in this gorgeous luxury 1 bedroom town house apartment on Old Bend Redmond Highway. Located on the ground floor, newly built. Queen Bedroom, high ceilings, lots of light. The kitchen has all new appliances and is fully stocked. Granite counter tops …see more

from $125 / night

$800 - $1,200 / week

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from $125 / night

26

Vacation home in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Enjoy incredible views of the Deschutes River during your stay at 'River Glen Retreat,' a 3-bedroom, 2.5-bathroom vacation rental house in Bend! The 2,500-square-foot home is located on the banks of the river and has large windows which provide guests with unbeatable vi …see more

from $315 / night

$2,205 - $3,465 / week

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Responds fast!
avg. 40 minutes

from $315 / night

14

Bend Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown. This remodeled condo is part of the Pioneer Park Condos that are located along the Deschutes River. This second floor unit is perfectly situated. A lovely river trail …see more

from $90 / night

$585 - $1,200 / week

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from $90 / night

(4) Excellent 

31

Vacation home rental

Central Oregon / Bend

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Air conditioning
Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While Snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. It felt like home when …see more

from $400 / night

$2,800 / week

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Responds fast!
avg. 2 hours 48 minutes

from $400 / night

15

Vacation home in Bend

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
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 full …see more

from $195 / night

$1,200 - $1,700 / week

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from $195 / night

15

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
This is a newer two-story, 3 bedroom/2.5 bath house with a bonus room upstairs. Living room, full kitchen, dining room and half bath on first floor as well as the laundry facility with full size washer and dryer. Gas fireplace in the living room. Upstairs you have the m …see more

from $225 / night

$1,400 - $1,800 / week

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from $225 / night

14

Bend ski home to rent.

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Ski
  • Child friendly
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 Villag …see more

from $200 / night

$1,400 / week

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from $200 / night

8

Vacation home in Bend

Central Oregon / Bend

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Pet friendly
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 st …see more

from $60 / night

$420 / week

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from $60 / night

(3) Excellent 

8

Vacation home in Bend

Central Oregon / Bend

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Pet friendly
This house is right on the Deschutes River. You can walk one way to town (through Drake Park), and the other way also along the river to the Old Mill District. There really isn't a better location in Bend. One bedroom with queen bed and a really comfortable queen hid …see more

from $150 / night

$730 - $1,250 / week

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Responds fast!
avg. 3 hours 38 minutes

from $150 / night