25 Best Sisters Vacation rentals on Holiday Lettings - Cabins

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259 Vacation rentals

34

Vacation home in Sisters

Central Oregon / Sisters

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
If you're looking for a peaceful Central Oregon getaway to share with your large group, consider staying at this stunning Sisters vacation rental. Custom built by an architect with experience designing churches, this cathedral-esque home boasts five bedrooms, a loft, a …see more

from $149 / night

$1,043 / week

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avg. 2 hours 13 minutes

from $149 / night

(1) Excellent 

26

Vacation home in Sisters

Central Oregon / Sisters

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Escape the hustle and bustle of daily life when you stay at this charming, dog-friendly studio. Enjoy the peace and quiet of the incredible Central Oregon landscape while you reconnect with your loved one and spend time exploring the beautiful natural surroundings. Si …see more

from $54 / night

$378 / week

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avg. 2 hours 13 minutes

from $54 / 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

$1,050 / week

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avg. 2 hours 13 minutes

from $150 / night

26

Vacation home with shared pool in Sisters

Central Oregon / Sisters

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
You can't beat this practically new home on the west side of Pine Meadow Village. A corner lot with an awesome view of Three Sisters. Relax on our large covered porch and watch the mountains, sunset, and roaming deer. Or just relax in our living room and view it all …see more

from $209 / night

$1,463 / week

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avg. 36 minutes

from $209 / night

25

Home rental in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This rustic cabin in Sisters, OR offers access to a shared pool, tennis courts, and proximity to wilderness and conveniences for up to eight guests to feel at home! Sitting in the quiet and relaxed Tollgate community three miles outside of Sisters, a quick drive will b …see more

from $99 / night

$693 / week

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avg. 2 hours 13 minutes

from $99 / 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. …see more

from $99 / night

$693 / week

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Responds fast!
avg. 2 hours 13 minutes

from $99 / night

(1) Excellent 

24

Vacation home in Sisters

Central Oregon / Sisters

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
This traditional log cabin in Sisters, OR will accommodate up to seven travelers to enjoy modern amenities, a shared pool, and tennis courts! Part of the Tollgate community just three miles from the heart of Sisters, you'll enjoy bike paths and easy access to outdoor f …see more

from $67 / night

$469 / week

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avg. 2 hours 13 minutes

from $67 / night

8

Vacation home rental

Central Oregon / Sisters

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
Spacious family-friendly home located on the 16th fairway of Big Meadow Golf Course. Large open kitchen with granite countertops and bar seating. The dining area adjoins the Great Room where you can dine, play cards or games, or lounge in front of the fireplace. Two be …see more

from $325 / night

$2,275 / week

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from $325 / night

(2) Excellent 

13

Vacation home in Sisters

Central Oregon / Sisters

4 9 5 nights min

  • 4 bedrooms
  • Sleeps 9
  • 5 nights min
  • Child friendly
  • Air conditioning
Serious Quilters will love this house and location!! We have a 2500 Square feet home with 4 bedrooms and a home office (that easily converts to a 5th bedroom). We can sleep 9 on beds and another 4 on air mattresses. $350/night with a minimum of 4 nights. Great outdo …see more

from $425 / night

$2,800 - $3,850 / week

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from $425 / night

38

Vacation home in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This comfortable, riverfront home in Sister, OR is the perfect spot for your next getaway! Up to eight guests will feel at home here with modern furnishings, access to the Wychus Creek right out the back door, and your own private hot tub. Located in a quiet neighborho …see more

from $99 / night

$693 / week

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avg. 2 hours 13 minutes

from $99 / night

45

Sisters Vacation home rental

Central Oregon / Sisters

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
Plan a rejuvenating trip to Central Oregon at Sisters Mountain View Ranch, where you'll find 30 acres of private land and a private hot tub for a family of up to nine to have a great time! Located a few miles south of downtown Sisters, you'll enjoy privacy while still …see more

from $99 / night

$693 / week

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avg. 2 hours 13 minutes

from $99 / night

42

Home rental in Sisters

Central Oregon / Sisters

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Air conditioning
Say hello to a relaxing, laid-back Central Oregon getaway when you stay at this secluded Sisters vacation rental. Nestled on five acres just outside the city limits, this home boasts a private hot tub and a wood-burning fireplace in addition to convenient amenities such …see more

from $149 / night

$1,043 / week

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avg. 2 hours 13 minutes

from $149 / night

33

Vacation home rental

Central Oregon / Sisters

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Rejoice in the scent of pine trees, sage, and beautiful desert landscape when you take a retreat to Central Oregon. This cute bungalow in Sisters is the perfect home base for a group of six, featuring a large outdoor patio with gazebo seating in any weather, access to a …see more

from $90 / night

$630 / week

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avg. 2 hours 13 minutes

from $90 / night

26

Home rental in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Retreat to this large, spacious home in Sisters with your family and friends - plus the family dog! You'll have plenty of room to relax, a lovely deck with a gas grill, and a great location near town and lots of outdoor recreation. Located in the quiet Squaw Creek com …see more

from $100 / night

$700 / week

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avg. 2 hours 13 minutes

from $100 / night

(1) Very Good 

28

Home rental in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
If you're planning a Central Oregon getaway, you can't go wrong with a stay at this dog-friendly Bend vacation rental. Whether you're lounging on the spacious decks, admiring the mountain views as you soak in the private hot tub, or relaxing in front of the wood stove, …see more

from $134 / night

$938 / week

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avg. 2 hours 13 minutes

from $134 / night

30

Home rental in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Whether you're here for the famous Sisters Rodeo or you're just looking for a quiet home-base from which to explore Central Oregon, you can't go wrong with this charming cottage. Your friends and family will love soaking in the private hot tub, while your dog will love …see more

from $109 / night

$763 / week

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avg. 2 hours 13 minutes

from $109 / night

32

Vacation home in Sisters

Central Oregon / Sisters

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Take a trip to Sisters and enjoy a stay at this charming house right in downtown. With entertainment, a central location, and a separate studio for privacy, up to six guests will have a great time here! Located across from the Village Green City Park just a couple bloc …see more

from $86 / night

$602 / week

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avg. 2 hours 13 minutes

from $86 / night

(3) Good 

24

Vacation home in Sisters

Central Oregon / Sisters

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Sisters Tollgate Cabin is nestled among the pine trees on the edge Deschutes National Forest. Knotty pine walls and western decor provide rustic ambience in this two bedroom vacation cabin. Downtown Sisters is just three miles away, where art, culture, and dining abou …see more

from $74 / night

$518 / week

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avg. 2 hours 13 minutes

from $74 / night

30

Vacation apartment with shared pool in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This condo takes full advantage of the gorgeous views of the 10th Fairway plus the North, the South Sister Mountains as well as Broken Top. There is a large Trex deck where the views are stunning to sunbathe, enjoy the golfers, evening BBQs with family or just relax wi …see more

from $225 / night

$1,575 - $2,168 / week

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from $225 / night

24

Home rental in Sisters

Central Oregon / Sisters

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
This charming 1930's-era bungalow in the heart of historic Sisters offers a comfortable and convenient way to enjoy a romantic or adventure-packed vacation in the Cascades. Set on a quiet street within walking distance to restaurants, coffee shops, galleries and the th …see more

from $49 / night

$343 / week

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avg. 2 hours 13 minutes

from $49 / night

20

Vacation apartment with shared pool in Sisters

Central Oregon / Sisters

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This cozy, charming condo is in a prime location. Walk to most facilities and enjoy the stunning scenery Black Butte offers every time you look outside or venture onto the deck! Perfect for the sunbather or wildlife buff or photographer. This condo is ideal for exper …see more

from $175 / night

$1,225 - $1,801 / week

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from $175 / night

23

Vacation home with shared pool in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This spacious (1,744 sq. ft) home has loads of charm and is beautifully updated. Surrounded by Ponderosa Pines and within a short walk to the popular Paulina Springs Pool area, it will be ideal for your family vacation. Paulina Springs Pool, which is as unique as Black …see more

from $265 / night

$1,855 - $2,683 / week

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from $265 / night

28

Vacation home with shared pool in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
GM#349 is a spacious 2,855 sq. foot reverse living home that sits on a quiet cul-de-sac at Black Butte Ranch. It sits on over an acre with stunning views of the #14 Fairway of Glaze Meadow! When you enter the great room of this home, you are struck by the beautiful wo …see more

from $299 / night

$2,093 - $2,933 / week

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from $299 / night

32

Vacation home with shared pool in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This vacation home sits on a beautifully landscaped home site with large Ponderosas and vine maple, a perfect habitat for abundant birds and wildlife. The spacious back deck is very private, bordering forest land and there are bird houses everywhere for nesting and a wo …see more

from $295 / night

$2,065 - $2,903 / week

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from $295 / night

25

Vacation home with shared pool in Sisters

Central Oregon / Sisters

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
As you walk into this five bedroom house, you will feel as if you have come home! Charming decor and warmth will make you feel welcome and comfortable. The entry enters into the large great room, with an open concept living space of living room, dining room, and kitche …see more

from $485 / night

$3,395 - $4,300 / week

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from $485 / night