50 Best Central Oregon Vacation rentals on Holiday Lettings - House rentals

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Vacation rentals Sunriver
453 properties
Vacation rentals Black Butte Ranch
151 properties
Vacation rentals Bend
126 properties
Redmond
51 properties
Vacation rentals Sisters
21 properties
Cabins Camp Sherman
11 properties
La Pine
10 properties

Central Oregon

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827 Vacation rentals

26

Home accommodation in Black Butte Ranch

Central Oregon / Black Butte Ranch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Planning a trip to Central Oregon with your friends and loved ones? Consider staying at this memorable three-bedroom Black Butte Ranch home, which features a spacious patio, two master suites, and access to resort amenities such as a shared pool, a shared hot tub, tenni …see more

from $127 / night

$889 / week

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from $127 / night

36

Home accommodation in Sisters

Central Oregon / Sisters

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This comfortable vacation rental in Sisters is a fantastic place to plan your next Central Oregon adventure. Nestled in Tollgate, an authentic western-style community, when you stay here you will have easy access to city businesses, shared amenities such as a pool, plus …see more

from $150 / night

$1050 / week

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from $150 / night

(1) Excellent 

19

Redmond Vacation home rental

Central Oregon / Redmond

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
With rustic charm, access to the Eagle Crest Resort, and plenty of space for up to six lucky guests, this sprawling, single-level townhouse in the newly-built Creekside community is the perfect home-away-from-home for your next vacation! This cozy home offers luxurious …see more

from $89 / night

$623 / week

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from $89 / 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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Responds fast!
avg. 1 hour 17 minutes

from $59 / night

(1) Excellent 

7

Vacation apartment with shared pool in Sunriver

Central Oregon / Sunriver

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
The condo is a ground floor unit with two bedrooms and two baths. The bedrooms are on opposite sides of the unit with living area between. One bedroom has a bath with stand up shower and bedroom on other side has bathroom outside with tub/.shower combo. Condo comple …see more

from $95 / night

$595 / week

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from $95 / night

25

Vacation home rental

Central Oregon / Sunriver

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Planning your next trip to Central Oregon? Look no further than this incredible cabin! Located in the heart of Sunriver and near this community's amazing amenities, this recently remodeled vacation rental has a private hot tub, a gas fireplace, and plenty of fun options …see more

from $99 / night

$693 / week

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from $99 / night

28

Sunriver Vacation home rental

Central Oregon / Sunriver

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Looking for the perfect Sunriver getaway for your family or group? Consider this lovely four-bedroom home, which boasts a private hot tub and 10 complimentary SHARC passes in addition to a convenient location. Sunriver offers plenty of nearby, family-friendly entertainm …see more

from $136 / night

$952 / week

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from $136 / night

44

Vacation home in Redmond

Central Oregon / Redmond

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
This 3,200 square-foot home in Eagle Crest includes a private hot tub and great amenities inside and out, making this a great rental for family and friends alike! Located in the heart of Eagle Crest, this home is less than 20 miles from Sisters and Bend, and 38 miles fr …see more

from $99 / night

$693 / week

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from $99 / night

27

Home rental in Sunriver

Central Oregon / Sunriver

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
This wonderful two-bedroom, two-bath condo features a loft and a den. It is also dog-friendly and comes with six SHARC passes. It has fabulous views of the mountains and golf course. This Sunriver retreat sleeps eight with queen beds in each of the two bedrooms, one ups …see more

from $70 / night

$490 / week

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from $70 / night

(1) Excellent 

31

Sunriver Vacation home rental

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This spacious three-bedroom Sun River vacation rental offers a private hot tub, gas fireplace, expansive patio, and space for eight guests! Whether you're soaking up the sun or skiing the slopes, Tan Oak is the perfect destination location for the entire family! Walk to …see more

from $107 / night

$743 / week

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from $107 / night

36

Sunriver Vacation home rental

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This home at #39 Oregon Loop is a beautiful space with three bedrooms and two baths, a private hot tub, and eight passes to SHARC. The home located on the north side of Sunriver, near the North Store and the Woodlands Golf Course. This home features a romantic king mast …see more

from $175 / night

$1225 / week

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from $175 / night

22

Vacation home in La Pine

Central Oregon / La Pine

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
River Bend 1 River Bend 1 has everything you visit Central Oregon for; peace and quiet while recharging with the numerous outdoor activities available. This home, located a short five (5) miles south of the Sunriver Resort area, sits on three (3) acres of forest land …see more

from $125 / night

$750 - $1680 / week

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from $125 / night

32

Vacation home in Redmond

Central Oregon / Redmond

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
You'll be perched above the golf course in this deluxe townhome with resort amenities and modern conveniences for the whole group. Bring family or friends for a summer retreat or plan the perfect ski holiday! The two-story home is located in Eagle Crest Resort, a luxury …see more

from $70 / night

$490 / week

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from $70 / 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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from $99 / night

35

Vacation home in Sunriver

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Leave behind your worries and surround yourself with the tall trees and wide skies of Central Oregon! From easy access to golf, swimming, and a private hot tub to the stunning natural beauty just nearby, your new vacation home in Sunriver is just what you need to stay r …see more

from $122 / night

$848 / week

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from $122 / night

(1) Excellent 

36

Vacation home in Sunriver

Central Oregon / Sunriver

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Intimate and elegant, this dog-friendly Sunriver vacation home offers up to six guests a well-appointed condo in the Sunriver, with access to the Quelah community swimming pool, hot tub, and seasonal tennis courts. Located in a fabulous year-round destination, this home …see more

from $88 / night

$616 / week

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from $88 / night

(1) Good 

30

Home rental in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This newer craftsman style home is walking distance to Downtown Sisters. From the front porch you can view Black Crater. The upstairs family room has a large screen TV and wonderful skylights adding an abundance of natural light. There is a sleeper sofa in this room. Th …see more

from $87 / night

$609 / week

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from $87 / night

18

Home rental in Black Butte Ranch with shared pool

Central Oregon / Black Butte Ranch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
We just lowered our summer and fall rates plus if you book before March 31 we'll give you a $50 gift card to use anywhere on the ranch, so be sure to check it out. Our 2400 sq. foot executive dream 3 bedroom home has a "to-die-for" view of Mt. Jefferson, Glaze Meadow g …see more

from $295 / night

$1850 - $2195 / week

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from $295 / 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

7

Black Butte Ranch Vacation apartment rental

Central Oregon / Black Butte Ranch

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
This beautiful Central Oregon vacation rental condo has been newly remodeled with coordinated decor and fresh paint throughout the home. The dining room connects to a nice deck, with and outdoor table and seating for four. This condo is overlooking the 10th fairway at …see more

from $225 / night

$1575 / week

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from $225 / night

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

(3) Excellent 

23

Redmond Vacation apartment rental

Central Oregon / Redmond

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Enjoy this 1871sqft 3 bedroom 2.5 bath condo with a vaulted ceiling in the family room. This home comfortably sleeps 8 to 9 people with 1 king, 1 queen, 2 twin beds (1 w/ trundle), and a twin top/ full bottom bunk bed. The fully equipped kitchen features Granite Counter …see more

from $135 / night

$1055 - $1225 / week

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Responds fast!
avg. 2 hours 17 minutes

from $135 / night

24

Home rental in Black Butte Ranch with shared pool

Central Oregon / Black Butte Ranch

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning home will exceed all your vacation rental needs. The open floor plan will easily accommodate your extended family. A large river rock fireplace in the open great room, beautiful gourmet kitchen, television area for the kids, spacious decks and sweeping vie …see more

from $489 / night

$3424 - $4123 / week

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from $489 / 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

20

Vacation condo in Sunriver

Central Oregon / Sunriver

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary
This newly renovated place is one minute walk to the village. The village has shops, restaurants, ice skating, bounce houses, rock climbing and miniature golf. You will find three golf courses nearby. The sharc is a two minute drive and offers indoor/outdoor swimming po …see more

from $175 / night

$1225 / week

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from $175 / night

21

Vacation home accommodation

Central Oregon / Sunriver

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Surrounded by trees, this adorable, two story Sunriver cottage offers a gas grill, wood-burning fireplace, and space for up to six friends or family members. You'll have access to the Ranch Cabin shared pool and six SHARC passes. Located just one-and-a-half miles north …see more

from $87 / night

$603 / week

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from $87 / night

(10) Excellent 

9

Vacation apartment in Black Butte Ranch

Central Oregon / Black Butte Ranch

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
Lodge Condo 022 is a Signature rated, two bedroom, one full size bathroom townhouse style condominium. LC 022 has recently been updated; including the kitchen and bathroom. The décor and furnishings are traditional Northwest style of a high quality, including the art. …see more

from $285 / night

$1995 / week

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from $285 / 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

(5) Very Good 

7

Vacation home in Black Butte Ranch

Central Oregon / Black Butte Ranch

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
This Executive rated Central Oregon vacation home is furnished with many high quality touches, is set on a private lot backing to the Deschutes National Forest, has free wi fi throughout the home and a hot tub. The entry opens into a great room with vaulted ceilings and …see more

from $415 / night

$2905 / week

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from $415 / night

(1) Excellent 

31

Home rental in Sunriver

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This newly renovated home is located in the center of Sunriver in the popular Circle 4 Cabin complex, which boasts its own on-site swimming pool, and a private hot tub. This home is about 17 miles from Bend, and 21 miles from Mt. Bachelor, located in the heart of Sunriv …see more

from $99 / night

$693 / week

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from $99 / night

26

Home rental in Black Butte Ranch with shared pool

Central Oregon / Black Butte Ranch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This wonderful vacation home feels like new with upgrades throughout. Walk into the expansive entry and the beautiful decorator touches and colors are everywhere. The living room is open to the kitchen and dining room, making it easy to converse with the cooks! The kitc …see more

from $265 / night

$1855 - $2555 / week

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from $265 / night

(2) Excellent 

15

Sunriver Vacation home rental

Central Oregon / Sunriver

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Experience the natural beauty of Sunriver from this quiet location near the national forest. Enjoy views of the large common area and wildlife from your deck and from the many windows in the great room. Use the 3 single bikes and the tandem (in season) to bike the 30 …see more

from $185 / night

$850 - $1400 / week

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from $185 / night

35

Vacation home rental

Central Oregon / Redmond

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
This truly wonderful single level in the Ridge at Eagle Crest offers one of the best vacation locations in Central Oregon. The nearly 3,000 square foot open and air conditioned spacious floor plan is ideal for entertaining or spending time with all your friends and fami …see more

from $225 / night

$1575 / week

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from $225 / night

(5) Very Good 

8

Vacation home in Black Butte Ranch

Central Oregon / Black Butte Ranch

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
Executive four bedroom vacation rental in a central location to Big Meadow and Glaze Meadow Golf Courses, within walking distance to Paulina Pool or quick bike ride or walk to Glaze Meadow Recreation Center & Spa, and free wi fi throughout. Spring Home 015 features two …see more

from $340 / night

$2380 / week

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from $340 / night

30

Sunriver Vacation home rental

Central Oregon / Sunriver

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Dog-friendly Meadow House 19 has all the requirements for the perfect romantic getaway for two or even a fun-filled excursion for the small family of six (including SHARC passes). You'll have a hot tub! Your incredible lawn is ideally suited for an old-fashioned picnic …see more

from $112 / night

$778 / week

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from $112 / night

(3) Excellent 

11

Vacation home in Black Butte Ranch

Central Oregon / Black Butte Ranch

3 12 1 night min

  • 3 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
One of the best family vacation settings and views on the Ranch. Enjoy meadow and mountain views from multi-level decks. Partial garage access for guests; set up with a ping pong table. This vacation rental at Black Butte Ranch sits on the end of a cul-de-sac with priva …see more

from $425 / night

$2975 / week

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from $425 / night

(4) Excellent 

6

Vacation apartment in Black Butte Ranch

Central Oregon / Black Butte Ranch

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
This central Oregon vacation rental condo is an end unit with quiet and peaceful views of the meadow and Cascade mountains from the deck. Great central Oregon views from alcove on main level and upstairs. Tiled and updated fixtures in baths. Kitchen is galley-type with …see more

from $220 / night

$1540 / week

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from $220 / 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

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

29

Home rental in Black Butte Ranch with shared pool

Central Oregon / Black Butte Ranch

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Expansive windows look onto the large decks which run the entire length of the home, and private, wooded home site. The deck is secluded and allows for private sunbathing or provides an ideal area to fire up the gas grill for those family evening bbq's after long days o …see more

from $250 / night

$1750 - $2555 / week

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from $250 / night