Sisters Holiday Rentals
House
10.0Exceptional
(103 Reviews)
2 Bedrooms
2 Baths
6 Guests
1438 ft²
Hot Tub
Fireplace/Heating
Pool
Balcony/Terrace
US $339/Night
7 Nights - US $2,370
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
6 Guests
2023.62 ft²
- Fireplace/Heating
- Pool
View
Pet Friendly
US $1,136/Night
7 Nights - US $7,949
Hotel
9.6Exceptional
(1002 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $215/Night
7 Nights - US $1,506
Condo
10.0Exceptional
(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $394/Night
7 Nights - US $2,757
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
2281.95 ft²
- Hot Tub
Skiing- Fireplace/Heating
- Pool
US $889/Night
7 Nights - US $6,224
Cottage
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $258/Night
7 Nights - US $1,805
Condo
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $448/Night
7 Nights - US $3,138
House
10.0Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $213/Night
7 Nights - US $1,490
Condo
10.0Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $429/Night
7 Nights - US $3,003
Luxury Holiday Rentals in Sisters
Over 859+ Luxury Holiday Rentals in or Near Sisters
House
- Bend
- ·
- Black Butte Ranch
- 1.25 mi to center
9.8Exceptional
(50 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen
Parking
US $3,449/Night
7 Nights - US $24,145
House
- Bend
- ·
- Black Butte Ranch
- 0.53 mi to center
9.2Exceptional
(5 Reviews)
7 Bedrooms
9 Baths
22 Guests
5145 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,938/Night
7 Nights - US $13,564
House
10.0Exceptional
(39 Reviews)
7 Bedrooms
5 Baths
18 Guests
5069 ft²
- Skiing
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,775/Night
7 Nights - US $12,424
House
- Bend
- ·
- Black Butte Ranch
- 0.89 mi to center
1 Bedroom
1 Bath
12 Guests
2400.35 ft²
Private Pool- Hot Tub
Spa- Fireplace/Heating
US $1,670/Night
7 Nights - US $11,691
House
- Bend
- ·
- Black Butte Ranch
- 1.07 mi to center
6 Bedrooms
5 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
Air Conditioner
US $1,620/Night
7 Nights - US $11,340
House
- Bend
- ·
- Black Butte Ranch
- 1.21 mi to center
3 Bedrooms
3 Baths
8 Guests
2518.75 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,597/Night
7 Nights - US $11,180
House
- Bend
- ·
- Black Butte Ranch
- 0.40 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
5 Baths
18 Guests
4000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $1,578/Night
7 Nights - US $11,047
House
- Bend
- ·
- Black Butte Ranch
- 1.67 mi to center
8.0Excellent
(18 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,561/Night
7 Nights - US $10,925
House
- Bend
- ·
- Black Butte Ranch
- 0.93 mi to center
9.8Exceptional
(18 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,480/Night
7 Nights - US $10,361
Top-Rated Holiday Rentals with a Pool in Sisters
Over 605+ The Best Private Villas and Holiday Rentals in Sisters with a Pool
House
10.0Exceptional
(217 Reviews)
3 Bedrooms
2 Baths
8 Guests
1650 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $242/Night
7 Nights - US $1,694
House
- Bend
- ·
- Black Butte Ranch
- 1.23 mi to center
10.0Exceptional
(121 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $489/Night
7 Nights - US $3,425
House
- Bend
- ·
- Black Butte Ranch
- 0.48 mi to center
10.0Exceptional
(92 Reviews)
3 Bedrooms
2 Baths
11 Guests
1600 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $771/Night
7 Nights - US $5,400
House
- Bend
- ·
- Black Butte Ranch
- 0.46 mi to center
10.0Exceptional
(91 Reviews)
4 Bedrooms
3 Baths
13 Guests
2300 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $960/Night
7 Nights - US $6,720
House
- Bend
- ·
- Black Butte Ranch
- 0.17 mi to center
10.0Exceptional
(66 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $491/Night
7 Nights - US $3,436
House
- Bend
- ·
- Black Butte Ranch
- 1.06 mi to center
10.0Exceptional
(64 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $632/Night
7 Nights - US $4,422
House
- Bend
- ·
- Black Butte Ranch
- 0.85 mi to center
10.0Exceptional
(62 Reviews)
5 Bedrooms
4 Baths
10 Guests
2800 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $590/Night
7 Nights - US $4,130
House
10.0Exceptional
(61 Reviews)
4 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $430/Night
7 Nights - US $3,009
House
- Bend
- ·
- Black Butte Ranch
- 1.18 mi to center
10.0Exceptional
(55 Reviews)
4 Bedrooms
3 Baths
10 Guests
2855 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $911/Night
7 Nights - US $6,374
Pet-Friendly Holiday Rentals in Sisters
Over 288+ Pet-Friendly Holiday Rentals in or Near Sisters
Cabin
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $437/Night
7 Nights - US $3,059
House
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
7 Guests
1786.81 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $560/Night
7 Nights - US $3,923
House
9.6Exceptional
(5 Reviews)
1 Bedroom
2 Baths
5 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $469/Night
7 Nights - US $3,284
House
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
4 Guests
1250 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $394/Night
7 Nights - US $2,759
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
10 Guests
1550 ft²
- Hot Tub
- Fireplace/Heating
- View
- Pet Friendly
US $419/Night
7 Nights - US $2,931
Condo
- Bend
- ·
- Black Butte Ranch
- 1.28 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
852 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $422/Night
7 Nights - US $2,955
Cabin
- Bend
- ·
- Black Butte Ranch
- 0.29 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1280 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $433/Night
7 Nights - US $3,034
Condo
9.8Exceptional
(118 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $219/Night
7 Nights - US $1,536
Condo
9.8Exceptional
(117 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $226/Night
7 Nights - US $1,583
Large Holiday Rentals and Private Villas in Sisters
Over 252+ Large Holiday Rentals and Private Villas in or Near Sisters
Apartment
8.0Excellent
(2 Reviews)
1 Bedroom
5 Baths
14 Guests
3200 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $872/Night
7 Nights - US $6,101
House
- Bend
- ·
- Black Butte Ranch
- 0.53 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
6 Baths
20 Guests
4789.94 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $550/Night
7 Nights - US $3,850
House
1 Bedroom
3 Baths
10 Guests
2642 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $457/Night
7 Nights - US $3,196
House
- Bend
- ·
- Black Butte Ranch
- 0.89 mi to center
9.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
10 Guests
3143.06 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
US $189/Night
7 Nights - US $1,323
New
House
- Bend
- ·
- Black Butte Ranch
- 0.24 mi to center
4 Bedrooms
3 Baths
10 Guests
- Pet Friendly
- Kitchen
Internet
Child Friendly
US $783/Night
7 Nights - US $5,484
House
- Bend
- ·
- Black Butte Ranch
- 1.59 mi to center
10.0Exceptional
(170 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $797/Night
7 Nights - US $5,577
House
- Bend
- ·
- Black Butte Ranch
- 1.36 mi to center
10.0Exceptional
(49 Reviews)
4 Bedrooms
5 Baths
10 Guests
2838 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $960/Night
7 Nights - US $6,723
House
- Bend
- ·
- Black Butte Ranch
- 1.08 mi to center
10.0Exceptional
(47 Reviews)
4 Bedrooms
4 Baths
10 Guests
3923 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $1,245/Night
7 Nights - US $8,713
House
- Bend
- ·
- Black Butte Ranch
- 1.52 mi to center
10.0Exceptional
(44 Reviews)
5 Bedrooms
4 Baths
14 Guests
4500 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $996/Night
7 Nights - US $6,975
Wheelchair Accessible Holiday Homes in Sisters
Over 14+ Wheelchair Accessible Holiday Homes in or Near Sisters
House
4.8Average
(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
1033 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $262/Night
7 Nights - US $1,834
House
- Bend
- ·
- Black Butte Ranch
- 0.57 mi to center
3 Bedrooms
3 Baths
9 Guests
1937.5 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $716/Night
7 Nights - US $5,014
House
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $838/Night
7 Nights - US $5,866
Apartment
5.0Average
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $138/Night
7 Nights - US $966
House
1 Bedroom
2 Baths
6 Guests
1442.36 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $150/Night
7 Nights - US $1,050
Apartment
5.0Average
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $987
Hotel
9.4Exceptional
(94 Reviews)
6 Baths
696.07 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $382/Night
7 Nights - US $2,675
Apartment
4.7Average
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $130/Night
7 Nights - US $910
House
- Bend
- ·
- Black Butte Ranch
- 0.86 mi to center
4.2Average
(50 Reviews)
5 Bedrooms
3 Baths
12 Guests
2382 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $450/Night
7 Nights - US $3,150
Sisters Private Villas and Holiday Homes Under $200
Over 65+ Sisters Private Villas and Holiday Homes Under $200
Apartment
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $191/Night
7 Nights - US $1,334
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
7 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $109/Night
7 Nights - US $763
Hotel
9.6Exceptional
(199 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,318
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
230 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $172/Night
7 Nights - US $1,207
House
9.2Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
7 Guests
1399.31 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $148/Night
7 Nights - US $1,036
Apartment
9.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $179/Night
7 Nights - US $1,251
House
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $193/Night
7 Nights - US $1,353
Apartment
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $191/Night
7 Nights - US $1,338
New
House
3 Bedrooms
1 Bath
9 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $187/Night
7 Nights - US $1,307
Instantly Bookable Holiday Homes in Sisters
Over 569+ Instantly Bookable Holiday Homes in or Near Sisters
Cabin
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $321/Night
7 Nights - US $2,250
Condo
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $359/Night
7 Nights - US $2,514
Condo
- Bend
- ·
- Black Butte Ranch
- 1.32 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $518/Night
7 Nights - US $3,624
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
3 Baths
7 Guests
1350 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $454/Night
7 Nights - US $3,181
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $232/Night
7 Nights - US $1,625
Condo
- Bend
- ·
- Black Butte Ranch
- 1.28 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $773/Night
7 Nights - US $5,412
Condo
- Bend
- ·
- Black Butte Ranch
- 1.43 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $612/Night
7 Nights - US $4,283
Condo
- Bend
- ·
- Black Butte Ranch
- 1.43 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $523/Night
7 Nights - US $3,662
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $457/Night
7 Nights - US $3,202
Book a Last Minute Place to Stay in Sisters
About Casai's Private Villas and Holiday Rentals in Sisters
Discover more than 868 vacation rentals available in Sisters. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Sisters.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Sisters, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Sisters. On average, places to stay near Sisters offer 1567.14 ft², with nightly prices averaging US $541.
With Casai, finding and comparing holiday rentals in Sisters is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Sisters
| Type | Count |
|---|---|
| Vacation Homes | 641 |
| Holiday Apartments | 40 |
| Cottages | 5 |
Use these Quick Filters to Find a Holiday Rental in Sisters
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Sisters.
Weather in Sisters, OR
View the weather forecast for Sisters before booking your Sisters Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 15°F
March - May
High 69°F Low 30°F
June - August
High 88°F Low 44°F
September - November
High 74°F Low 32°F
Top Attractions Around Sisters, OR
Casai offers a large selection of top attractions around Sisters . Research things to do on your vacation before you visit Sisters.
Other Places to Stay in Sisters, OR
Frequently Asked Questions About Sisters?
What are the top holiday rentals in Sisters?
With numerous options available in Sisters, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Sisters:
- Enjoy Our Family Friendly Home In Tollgate
- Hot Tub + Golf Views | 3 King Suites + Game Loft
- Contemporary Cozy Cabin: Bikes, Outdoor Fire Table, and EV Charging
- Home with a private hot tub, shared pool, & National Forest at your backdoor
- 8+ Acre Waterfront Home w/Mountain Views & Pickleball Fun! Close to Town.
- NEXT TO GLAZE MEADOW, CUTE, WITH MANY AMENITIES!
- Black Butte Ranch-GM on 7th Hole. Major Upgrades! Ranch Favorite!
- SM BBR home - Perfect for two families!
- Prime location! Recent remodel. On the 13th green! Minutes to Paulina Pool!
- 5 Bedroom-2 w/King Beds, 4 Decks, Screened-in Breezeway. TRUE BLACK BUTTE FEEL!
How many holiday rentals have private pools in Sisters?
Discover a selection of holiday rentals with private pools near Sisters with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Cozy home with shared pool, sauna, golf, private hot tub & deck - dog-friendly
- South Meadow 23
- Dog-friendly home with grill, deck, firepit, balcony, & mountain view
- Three Peaks Hideaway
Which holiday homes in Sisters are best for families?
If you're searching for a family-friendly holiday home in Sisters, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Sisters:
How many Casai.com holiday rentals are available in Sisters?
As of 2026, Casai boasts over 868 properties listed in the Sisters area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Sisters.
People Also Ask
Finding the best prices in Sisters
Map
