50 Best Bend Vacation rentals on Holiday Lettings - Apartments

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127 Vacation rentals

25

Vacation home rental

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Just a short walk from Downtown Bend, is this gorgeous award-winning, 4 bedroom, 2.5 bath home. Awbrey House is applauded for its fine craftsmanship! This well appointed home features a gourmet kitchen with stainless steel appliances, including a Sub-Zero refrigerator a …see more

from $220 / night

$1540 / week

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from $220 / night

10

Bend Vacation studio rental

Central Oregon / Bend

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • 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 $59 / night

$413 / week

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avg. 1 hour 17 minutes

from $59 / 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 38 minutes

from $200 / night

23

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Located in River Wild, an exclusive and secluded neighborhood in the Mt. Bachelor Village Resort, Big Eddy features a spacious, open floor plan and a gourmet kitchen with stainless steel appliances and 5 burner gas range. The King Master Suite, which has private access …see more

from $180 / night

$1260 / week

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from $180 / night

21

Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
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 fo …see more

from $87 / night

$603 / week

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Responds fast!
avg. 3 hours 42 minutes

from $87 / night

15

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $225 / night

$1400 - $1800 / week

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from $225 / night

10

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 $65 / night

$455 / week

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from $65 / 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 $99 / night

$693 / week

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Responds fast!
avg. 3 hours 42 minutes

from $99 / 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
Canal view is a beautiful home located on the canal near the Old Mill District. This four-bedroom home features airy, open living spaces inside, and landscape lighting, a stone patio and natural gas fire pit outside. The gourmet kitchen features beautiful cabinets, gran …see more

from $200 / night

$1400 / week

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from $200 / 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 - $1250 / week

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Responds fast!
avg. 3 hours 17 minutes

from $150 / 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 …see more

from $240 / night

$1680 / week

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from $240 / night

(5) Excellent 

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

(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

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

(1) Excellent 

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
  • Car not necessary
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 $98 / night

$700 - $900 / week

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Responds fast!
avg. 3 hours 0 minutes

from $98 / night

14

Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $130 / night

$775 - $1200 / week

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from $130 / night

(4) Excellent 

13

Bend Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
This upstairs unit offers convenient access to all of Bend. Down town is less than a mile and the Shops at the Old Mill even closer. Spacious living area with the living, dining and kitchen open. Small deck off the living room provides fantastic sunsets over the Cascade …see more

from $150 / night

$800 - $1300 / week

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from $150 / night

10

Bend Vacation home rental

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Enjoy the luxury of a private, gated golf community in this beautifully-furnished townhome. Villa #6 is a two-bedroom, two-bath townhouse located in the quiet community of Broken Top. Enjoy beautiful views of the 18th Fairway of the privately-operated Broken Top Golf Co …see more

from $180 / night

$1260 / week

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from $180 / 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

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 eateries of Bend's vibrant downtown. The bakeries and breweries of the Galveston St corridor a …see more

from $210 / night

$1200 - $1700 / week

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from $210 / night

(1) Excellent 

10

Vacation home rental

Central Oregon / Bend

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
Location, Location, Location! Bend Zen a quaint, 1 Bedroom/1 Bath home ideally located near downtown Bend. Situated between Bend's premier shopping, dining, and entertainment establishments, and with centralized access to the outdoor recreation that makes Bend famous, y …see more

from $55 / night

$385 / week

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from $55 / 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

11

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 $65 / night

$455 / week

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from $65 / 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 beautiful home is located in the middle of the West side of Bend and minutes via bike to Bend's mountain biking epicenter, the Phil's Trail Head System. Bend has been rated #1 in the country for diver …see more

from $245 / night

$1715 / week

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from $245 / 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

31

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
Widgi Creek #15 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 to …see more

from $180 / night

$1260 / week

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from $180 / 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
Big Boulder is a gorgeous 3 bedroom, 2.5 bath home, in the River Wild Development of Mount Bachelor Village. Looking for a peaceful retreat in a quiet, forest setting? This home is nestled among large Ponderosa Pines and 15 in Bend's desirable Westside. The Deschutes Ri …see more

from $180 / night

$1260 / week

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from $180 / night

(2) 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

$633 / week

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Responds fast!
avg. 1 hour 14 minutes

from $109 / night

12

Home rental in Bend

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Our 3 bedroom 2 bath house, located right near the Old Mill district, is the perfect basecamp for your adventure in Central Oregon. You'll find comfort with 2 Queen beds, 1 California King, an open kitchen & living area, a garage and a fenced yard. Our home is great fo …see more

from $299 / night

$2000 / week

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Responds fast!
avg. 1 hour 48 minutes

from $299 / night

15

Bend Vacation home accommodation

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
The best way to enjoy your trip to Bend Oregon. The Pioneer Park Condominiums are located next to the beautiful Pioneer Park along the banks of the Deschutes River. With access to the river trail you will find hours of relaxing strolls with exciting views of the river o …see more

from $89 / night

$750 - $1200 / week

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from $89 / night

14

Bend Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • 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 St with easy access to Century Drive and …see more

from $210 / night

$1200 - $1700 / week

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from $210 / night

15

Bend Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
Excellent home for 2 couples or a family with two or three children. A newer house with tiled floor in the living room and dining room. Kitchen has open access to the living room keeping the cook with the company and family. Unless, of course, you prefer to grill outdoo …see more

from $150 / night

$800 - $1050 / week

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from $150 / night

23

Vacation home in Bend

Central Oregon / Bend

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Air conditioning
You'll love this 4 Bedroom/3.5 Bath one-of-a-kind house, located in a one-of-a-kind spot! This townhome is in a gated subdivision on the Deschutes River. Take in the seasonal rituals of wildlife on the river. Spend your mornings and evenings on the deck by watching floc …see more

from $133 / night

$931 / week

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from $133 / night

(2) 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

(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 family reunions or a getaway for several couples. Most of the rooms face the Cascade Mountains, and offer views of the …see more

from $290 / night

$2030 / week

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from $290 / night

(52) 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

$1125 - $1300 / week

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Responds fast!
avg. 3 hours 3 minutes

from $169 / night

(6) 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

(1) Excellent 

26

Vacation home in Bend

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

(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 $179 / night

$1175 - $1500 / week

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from $179 / night

(12) Very Good 

23

Vacation home with shared pool in Bend

Central Oregon / Bend

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Located 7.5 miles southwest of Sunriver, this home naturally provides the peace and quiet you have been longing for. You will enjoy the splendid hardwood floors and expansive living space with log accents. The spacious living room provides plenty of room for your friend …see more

from $325 / night

$2275 / week

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from $325 / night