Sisters Holiday Rentals
House
10.0Exceptional
(138 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
Hot Tub
Parking
Pool
Ocean View
US $296/Night
7 Nights - US $2,072
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
6 Guests
2023.62 ft²
- Parking
- Pool
View
Air Conditioner
US $1,136/Night
7 Nights - US $7,949
Hotel
9.8Exceptional
(910 Reviews)
1 Bath
- Hot Tub
Breakfast- Parking
- Pool
US $281/Night
7 Nights - US $1,965
House
10.0Exceptional
(104 Reviews)
2 Bedrooms
2 Baths
6 Guests
1438 ft²
- Hot Tub
- Pool
Balcony/Terrace
Kitchen
US $317/Night
7 Nights - US $2,217
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
2281.95 ft²
- Hot Tub
- Parking
- Pool
Skiing
US $454/Night
7 Nights - US $3,178
Condo
10.0Exceptional
(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $378/Night
7 Nights - US $2,646
Cottage
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $282/Night
7 Nights - US $1,972
Condo
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $371/Night
7 Nights - US $2,600
Condo
10.0Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $399/Night
7 Nights - US $2,796
Luxury Holiday Rentals in Sisters
Over 862+ Luxury Holiday Rentals in or Near Sisters
House
- Bend
- ·
- Black Butte Ranch
- 0.93 mi to center
9.8Exceptional
(19 Reviews)
7 Bedrooms
4 Baths
17 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,864/Night
7 Nights - US $13,050
House
- Bend
- ·
- Black Butte Ranch
- 1.68 mi to center
9.0Exceptional
(8 Reviews)
5 Bedrooms
3 Baths
14 Guests
3600 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,854/Night
7 Nights - US $12,980
House
10.0Exceptional
(39 Reviews)
7 Bedrooms
5 Baths
18 Guests
5069 ft²
- Parking
- Pool
- Skiing
- Balcony/Terrace
US $1,775/Night
7 Nights - US $12,424
House
- Bend
- ·
- Black Butte Ranch
- 0.68 mi to center
6 Bedrooms
4 Baths
13 Guests
- Parking
Spa- Kitchen
Internet
US $1,767/Night
7 Nights - US $12,369
House
- Bend
- ·
- Black Butte Ranch
- 1.07 mi to center
6 Bedrooms
5 Baths
10 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $1,745/Night
7 Nights - US $12,218
House
- Bend
- ·
- Black Butte Ranch
- 0.72 mi to center
10.0Exceptional
(17 Reviews)
5 Bedrooms
3 Baths
16 Guests
4100 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,722/Night
7 Nights - US $12,052
House
- Bend
- ·
- Black Butte Ranch
- 0.34 mi to center
10.0Exceptional
(29 Reviews)
6 Bedrooms
4 Baths
17 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $1,719/Night
7 Nights - US $12,033
House
- Bend
- ·
- Black Butte Ranch
- 1.21 mi to center
3 Bedrooms
3 Baths
8 Guests
2518.75 ft²
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
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
- Pool
- Spa
- Balcony/Terrace
US $1,529/Night
7 Nights - US $10,705
Top-Rated Holiday Rentals with a Pool in Sisters
Over 604+ The Best Private Villas and Holiday Rentals in Sisters with a Pool
House
10.0Exceptional
(220 Reviews)
3 Bedrooms
2 Baths
8 Guests
1650 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $335/Night
7 Nights - US $2,342
House
- Bend
- ·
- Black Butte Ranch
- 1.59 mi to center
10.0Exceptional
(171 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $679/Night
7 Nights - US $4,750
House
- Bend
- ·
- Black Butte Ranch
- 0.48 mi to center
10.0Exceptional
(92 Reviews)
3 Bedrooms
2 Baths
11 Guests
1600 ft²
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
US $1,028/Night
7 Nights - US $7,197
House
- Bend
- ·
- Black Butte Ranch
- 0.46 mi to center
10.0Exceptional
(91 Reviews)
4 Bedrooms
3 Baths
13 Guests
2300 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $729/Night
7 Nights - US $5,100
House
- Bend
- ·
- Black Butte Ranch
- 0.29 mi to center
10.0Exceptional
(91 Reviews)
3 Bedrooms
2 Baths
8 Guests
1963 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $707/Night
7 Nights - US $4,952
Cabin
- Bend
- ·
- Black Butte Ranch
- 1.36 mi to center
10.0Exceptional
(72 Reviews)
4 Bedrooms
2 Baths
8 Guests
1500 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $561/Night
7 Nights - US $3,924
House
- Bend
- ·
- Black Butte Ranch
- 1.57 mi to center
10.0Exceptional
(69 Reviews)
3 Bedrooms
3 Baths
8 Guests
2150 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $768/Night
7 Nights - US $5,377
House
- Bend
- ·
- Black Butte Ranch
- 0.17 mi to center
10.0Exceptional
(69 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $395/Night
7 Nights - US $2,762
House
- Bend
- ·
- Black Butte Ranch
- 1.06 mi to center
10.0Exceptional
(64 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $632/Night
7 Nights - US $4,422
Pet-Friendly Holiday Rentals in Sisters
Over 290+ Pet-Friendly Holiday Rentals in or Near Sisters
Cabin
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $454/Night
7 Nights - US $3,181
House
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
7 Guests
1786.81 ft²
- Parking
- View
- Air Conditioner
- Internet
US $444/Night
7 Nights - US $3,109
House
9.6Exceptional
(5 Reviews)
1 Bedroom
2 Baths
5 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $469/Night
7 Nights - US $3,284
House
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
4 Guests
1250 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $445/Night
7 Nights - US $3,114
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
10 Guests
1550 ft²
- Hot Tub
- Parking
- View
- Air Conditioner
US $419/Night
7 Nights - US $2,931
Condo
- Bend
- ·
- Black Butte Ranch
- 1.28 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
852 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $424/Night
7 Nights - US $2,967
New
House
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
10 Guests
2642 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $427/Night
7 Nights - US $2,992
Condo
9.8Exceptional
(124 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $217/Night
7 Nights - US $1,518
Condo
9.8Exceptional
(119 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $216/Night
7 Nights - US $1,514
Large Holiday Rentals and Private Villas in Sisters
Over 250+ Large Holiday Rentals and Private Villas in or Near Sisters
House
- Bend
- ·
- Black Butte Ranch
- 0.85 mi to center
10.0Exceptional
(62 Reviews)
5 Bedrooms
4 Baths
10 Guests
2800 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $584/Night
7 Nights - US $4,089
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
- Parking
- Pool
- Skiing
US $550/Night
7 Nights - US $3,850
House
- Bend
- ·
- Black Butte Ranch
- 1.18 mi to center
10.0Exceptional
(56 Reviews)
4 Bedrooms
3 Baths
10 Guests
2855 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,033/Night
7 Nights - US $7,228
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
- Parking
- Pool
- Skiing
US $189/Night
7 Nights - US $1,323
House
- Bend
- ·
- Black Butte Ranch
- 1.36 mi to center
10.0Exceptional
(50 Reviews)
4 Bedrooms
5 Baths
10 Guests
2838 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,001/Night
7 Nights - US $7,006
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
- Pool
- Spa
US $987/Night
7 Nights - US $6,906
House
- Bend
- ·
- Black Butte Ranch
- 1.52 mi to center
10.0Exceptional
(44 Reviews)
5 Bedrooms
4 Baths
14 Guests
4500 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,140/Night
7 Nights - US $7,979
House
- Bend
- ·
- Black Butte Ranch
- 1.16 mi to center
10.0Exceptional
(24 Reviews)
4 Bedrooms
3 Baths
12 Guests
3199 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,053/Night
7 Nights - US $7,371
House
- Bend
- ·
- Black Butte Ranch
- 1.54 mi to center
10.0Exceptional
(13 Reviews)
5 Bedrooms
3 Baths
12 Guests
4401 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,172/Night
7 Nights - US $8,205
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
- Kitchen
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
- Parking
- Pool
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
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $138/Night
7 Nights - US $966
House
1 Bedroom
2 Baths
6 Guests
1442.36 ft²
- Hot Tub
- Pool
- Balcony/Terrace
Child Friendly
US $150/Night
7 Nights - US $1,050
Apartment
5.0Average
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $141/Night
7 Nights - US $987
Hotel
9.4Exceptional
(94 Reviews)
6 Baths
696.07 ft²
- Hot Tub
- Breakfast
- EV Charge Station
- Parking
US $382/Night
7 Nights - US $2,675
Apartment
4.7Average
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
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 62+ Sisters Private Villas and Holiday Homes Under $200
New
Condo
2 Bedrooms
2 Baths
4 Guests
1215 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $125/Night
7 Nights - US $877
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
7 Guests
1797.57 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $109/Night
7 Nights - US $763
Hotel
9.6Exceptional
(219 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,318
Apartment
7.8Very Good
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
605 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $180/Night
7 Nights - US $1,262
House
9.2Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
7 Guests
1399.31 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $148/Night
7 Nights - US $1,036
House
5.0Average
(58 Reviews)
3 Bedrooms
2 Baths
6 Guests
1750 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $200/Night
7 Nights - US $1,400
House
5.0Average
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
Laundry
US $177/Night
7 Nights - US $1,239
House
5.0Average
(4 Reviews)
3 Bedrooms
3 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $167/Night
7 Nights - US $1,169
House
5.0Average
(3 Reviews)
5 Bedrooms
4 Baths
6 Guests
1184 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $112/Night
7 Nights - US $781
Instantly Bookable Holiday Homes in Sisters
Over 570+ Instantly Bookable Holiday Homes in or Near Sisters
Cabin
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $279/Night
7 Nights - US $1,956
Condo
10.0Exceptional
(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $359/Night
7 Nights - US $2,511
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $701/Night
7 Nights - US $4,906
Condo
- Bend
- ·
- Black Butte Ranch
- 1.43 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
US $539/Night
7 Nights - US $3,771
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $346/Night
7 Nights - US $2,422
Condo
- Bend
- ·
- Black Butte Ranch
- 1.43 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
US $509/Night
7 Nights - US $3,563
Condo
- Bend
- ·
- Black Butte Ranch
- 1.33 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
US $503/Night
7 Nights - US $3,522
Cabin
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Breakfast
- Pool
- Spa
US $405/Night
7 Nights - US $2,835
Cabin
- Bend
- ·
- Black Butte Ranch
- 1.34 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
214 ft²
- Hot Tub
- Pool
- Spa
- Kitchen
US $327/Night
7 Nights - US $2,292
Book a Last Minute Place to Stay in Sisters
About Casai's Private Villas and Holiday Rentals in Sisters
Discover more than 871 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 1570.18 ft², with nightly prices averaging US $535.
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.
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Top Accommodation Types in Sisters
| Type | Count |
|---|---|
| Vacation Homes | 638 |
| Holiday Apartments | 43 |
| 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
- Golf View Retreat | Hot Tub, 3 Kings & Pool Table
- View stunning sunsets and enjoy cozy comfort steps from the heart of Sisters.
- Home with a private hot tub, shared pool, & National Forest at your backdoor
- Sisters, OR Lodge – Pickleball, Private Creek, Hot Tub & Mt Views on 8.5 Acres
- NEXT TO GLAZE MEADOW, CUTE, WITH MANY AMENITIES!
- Black Butte Ranch-GM on 7th Hole. Major Upgrades! Ranch Favorite!
- Lovely setting on Aspen Lake
- Prime August Days Avail! Charming & Updated Black Butte Ranch Fairway Golf Home
- 3 Bed/3 bath on Golf Course/Two Large decks/bikes/Includes 7 bikes/2100 sq ft/
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
- Delightful escape near downtown with shared pool & hot tub, rec room, & large deck
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 871 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.
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