50 Best Bend Vacation rentals on Holiday Lettings - Apartments

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595 Vacation rentals

8

Vacation home in Bend

Central Oregon / Bend

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Pet friendly
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 st …see more

from $63 / night

$441 / week

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from $63 / night

15

Home rental in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Imagine watching sunsets over the Cascades looking across the Deschutes River. Walking to the Shops at the Old Mill. A mile from down town Bend. This spacious town home has two master suites. The first floor Queen Master has a large walk in closet and a gorgeous bathroo …see more

from $275 / night

$1,600 - $2,250 / week

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from $275 / 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

(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. 3 hours 30 minutes

from $195 / 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

(8) Very Good 

25

Home rental in Bend

Central Oregon / Bend

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
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 Desch …see more

from $69 / night

$483 / week

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Responds fast!
avg. 35 minutes

from $69 / 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. 2 hours 0 minutes

from $250 / 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

(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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from $165 / night

10

Vacation home in Bend

Central Oregon / Bend

1 4 Min stay varies

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

from $90 / night

$585 - $1,200 / week

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from $90 / night

14

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
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 Street with easy access to Century Driv …see more

from $210 / night

$1,200 - $1,700 / week

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from $210 / night

13

Vacation home in Bend

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
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 surro …see more

from $150 / night

$900 - $1,400 / week

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from $150 / 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

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

13

Vacation home in Bend

Central Oregon / Bend

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly
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 sh …see more

from $290 / night

$1,700 - $2,300 / week

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from $290 / night

13

Vacation home rental

Central Oregon / Bend

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Pet friendly
A newly remodeled 1 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 $60 / night

$420 / week

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from $60 / night

8

Vacation home rental

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

Inquire View

from $60 / 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

(2) Very Good 

15

Home rental in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
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. Minut …see more

from $210 / night

$1,350 - $1,800 / week

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from $210 / 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 $115 / night

$650 - $850 / week

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Responds fast!
avg. 1 hour 30 minutes

from $115 / 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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from $130 / 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

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

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

9

Vacation home in Bend

Central Oregon / Bend

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • 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

(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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Responds fast!
avg. 35 minutes

from $112 / 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

Vacation home in Bend

Central Oregon / Bend

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • 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

Inquire View

from $60 / night

10

Vacation home in Bend

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 $130 / night

$775 - $1,100 / week

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from $130 / night

25

Log cabin rental in Bend

Central Oregon / Bend

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
This classic log cabin exudes rustic country charm and offers 1,329 square feet of cozy living space. With views of the Deschutes River from all 3 bedrooms, the living room and the lofted patio, this Bend vacation rental cabin invites 7 guests to experience the essence …see more

from $125 / night

$875 - $1,645 / week

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Responds fast!
avg. 7 minutes

from $125 / 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

Inquire View

from $60 / 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

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

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

Inquire View

from $60 / 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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from $250 / night

14

Vacation home in Bend

Central Oregon / Bend

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly
Heyburn 3 is a newly remodeled ground floor home that is beautifully furnished and has lots of privacy. A large flat screen TV and gas fireplace in the living room adds to it's charm. The open floor plan allows for an easy flow from the kitchen to the dining area with a …see more

from $140 / night

$840 - $1,100 / week

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from $140 / night

(8) 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

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 $128 / night

$896 / week

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Responds fast!
avg. 35 minutes

from $128 / 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

9

Vacation home in Bend

Central Oregon / Bend

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • 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

Inquire View

from $60 / night