50 Best Bend Vacation rentals on Holiday Lettings - Apartments

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114 Vacation rentals

(3) Very Good 

14

Bend Vacation cottage rental

Central Oregon / Bend

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Hello! Here is your home away from home in Bend! Comfortable for a weekend or a month, our 1920's era west side 2 bedroom, 1 bath bungalow is in a quiet neighborhood just a block from the Deschutes River trail and First Street kayak rapids. Recently fully remodeled, it …see more

from $155 / night

$930 - $1160 / week

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Responds fast!
avg. 3 hours 36 minutes

from $155 / night

(44) Excellent 

27

Vacation cottage in Bend

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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

from $154 / night

$1025 / week

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Responds fast!
avg. 3 hours 3 minutes

from $154 / night

22

Vacation home in Bend

Central Oregon / Bend

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Need extra space for your large group? Cascade Peaks is a five-bedroom home very convenient to skiing at Mt. Bachelor Resort as well as world-class hiking and mountain bike trails. This three-level, architectural home features great views of Mt. Jefferson and a newly up …see more

from $220 / night

$1540 / week

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from $220 / night

(1) Excellent 

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

$633 / week

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Responds fast!
avg. 1 hour 16 minutes

from $109 / night

12

Vacation condo in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $139 / night

$789 / week

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Responds fast!
avg. 1 hour 16 minutes

from $139 / night

(3) Excellent 

37

Bend ski home to rent.

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Views from your front yard. Walk the butte and be in the park in 50 yds. The home is lovely furnished with tasteful furniture, granite counter tops, fireplace and landscaped backyard. The tall cathedral ceilings throughout the home are awe inspiring. This home can s …see more

from $135 / night

$900 / week

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from $135 / 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

$731 - $1250 / week

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Responds fast!
avg. 3 hours 18 minutes

from $150 / night

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 $200 / night

$1200 - $1830 / week

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Responds fast!
avg. 2 hours 43 minutes

from $200 / night

(1) Excellent 

25

Bend Vacation home rental

Central Oregon / Bend

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
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 a large family reunion or a getaway for several couples. Most of the rooms face the Cascade Mountains, and offer views …see more

from $290 / night

$2030 / week

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from $290 / night

32

Vacation home rental

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
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 …see more

from $300 / night

$2100 / week

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from $300 / night

18

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Looking for a peaceful retreat in a quiet, forest setting? Big Boulder is nestled among large ponderosa trees and 15 acres of undeveloped land just off Century Drive on Bend's desirable west side. The Deschutes River Trail is just out the door, and provides access to in …see more

from $180 / night

$1260 / week

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from $180 / night

(1) Excellent 

16

Home rental in Bend

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
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 thr …see more

from $250 / night

$1750 / week

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from $250 / night

(1) Excellent 

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 - $1290 / week

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Responds fast!
avg. 3 hours 58 minutes

from $165 / night

(2) Excellent 

30

Bend Vacation home rental

Central Oregon / Bend

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
The Space This house is 2 bedrooms with a secluded loft. The master bedroom has a Queen sized bed, walk in closet, and a full sized bathroom. The second bedroom has a Queen sized bed and has access to the second bathroom. Both bathrooms have custom concrete counters an …see more

from $250 / night

$1500 / week

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Responds fast!
avg. 1 hour 38 minutes

from $250 / night

(1) Excellent 

16

Home rental in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Ideally located to enjoy Bend’s Westside attractions, the Quincy House is just 3 blocks above Newport Avenue, home to many of Bend’s favorite restaurants and hangouts including Backporch Coffee Roasters, Chow and Spork. Built in 2000 by one of Bend’s most sought after …see more

from $200 / night

$1500 - $2052 / week

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Responds fast!
avg. 1 hour 29 minutes

from $200 / 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

$1925 / week

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Responds fast!
avg. 1 hour 51 minutes

from $275 / night

(2) 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

$1365 / week

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Responds fast!
avg. 1 hour 50 minutes

from $195 / night

(1) Very Good 

20

Vacation home rental

Central Oregon / Bend

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
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 …see more

from $148 / night

$1036 / week

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from $148 / night

20

Home rental in Bend

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Comfortable and cozy, Mirror Pond makes for an intimate stay in Bend. For a small family or couple, this house is on the banks of the Deschutes River near downtown, with an idyllic view of Drake Park at one of the most picturesque locations in Bend. This home is one of …see more

from $135 / night

$945 / week

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from $135 / night

15

Bend Vacation home rental

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
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 second floor unit is perfectly situated. A lovely river …see more

from $125 / night

$750 - $1100 / week

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from $125 / 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 56 minutes

from $130 / night

25

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
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 bedroo …see more

from $180 / night

$1260 / week

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from $180 / night

15

Vacation home in Bend

Central Oregon / Bend

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Pet friendly
Value inside and out with full kitchen with large table with extra seating at the counter. This is a newer two-story, three bedrooms, 2.5 bath house with a bonus room upstairs. On the main level you have a ‘great room’ with the living room, full kitchen, dining room and …see more

from $195 / night

$1200 - $1701 / week

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from $195 / night

14

Vacation home rental

Kansas / Council Grove

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • 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 $109 / night

$625 - $1050 / week

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from $109 / night

(1) Excellent 

37

Bend Vacation home rental

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
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 e …see more

from $240 / night

$1680 / week

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from $240 / night

(5) 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. A full kitchen w …see more

from $150 / night

$900 / week

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from $150 / night

(1) Very Good 

14

Vacation home in Bend

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
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 $125 / night

$750 - $1100 / week

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from $125 / night

17

Condo rental in Bend with shared pool

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • 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

$700 - $900 / week

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Responds fast!
avg. 3 hours 24 minutes

from $99 / night

27

Log cabin rental in Bend

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Blinn’s Landing Enjoyed and cherished by family and friends since 1951, this rustic log cabin, located at the confluence of Spring River and Deschutes River, adjacent to Sunriver Resort, offers a relaxing getaway with sparkling natural springs and picturesque mountain & …see more

from $289 / night

$2300 / week

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from $289 / night

28

Bend Vacation apartment rental

Central Oregon / Bend

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
*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 …see more

from $175 / night

$1050 - $3500 / week

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from $175 / night

28

Vacation home in Bend

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Located on a canal, this four-bedroom Bend-style home features airy, open living spaces inside, and outside space with landscape lighting, a stone patio and fire pit. Canal View is a beautiful home for your Bend vacation, with hardwood floors, a wrought-iron staircase a …see more

from $200 / night

$1400 / week

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from $200 / night

13

Vacation home in Bend

Central Oregon / Bend

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
Gorgeous new home on 5 acres, quiet yet close to town. Beautiful northwest mountain views. Beautifully furnished. Beautifully finished with granite counter tops, fine cabinetry and modern, elegant decor. Extra large windows allow in the light and beauty of the natural s …see more

from $150 / night

$900 - $1400 / week

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from $150 / night

36

Vacation home in Bend

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
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 cou …see more

from $245 / night

$1715 / week

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from $245 / night

11

Vacation home in Bend

Central Oregon / Bend

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
This house is in the heart of Bend and within two blocks of Drake Park and the historic downtown neighborhood and the river. Visit 10 Barrel and the food carts of Galveston. Drop into the Riverside Market. Walk to the Old Mill river parks, trails and playgrounds. Stroll …see more

from $150 / night

$800 - $1200 / week

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from $150 / night

12

Vacation home in Bend

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
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 $125 / night

$750 - $1100 / week

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from $125 / night

1