Property with pools
Properties in Pine Meadow Village, Tollgate and Black Butte Ranch that have a seasonal pool available. Most pools are open Memorial Day thru Labor Day.
22 properties available
Welcome to our charming and dog-friendly vacation rental nestled in the beautiful Tollgate community of Sisters, Oregon. This inviting home offers a perfect getaway for your family vacation to Central Oregon. With three bedrooms, a spacious yard, access to a seasonal pool, community basketball and tennis courts, your stay here promises to be a memo
Lariat House
3 Bedrooms
$129 - $778 / per night
3
bedrooms
2
baths
8
guests
5
(1)
The 4th Sister Lodge - Bottom floor, easy access to assigned parking. These condominiums are surrounded by Creekside park where Whychus Creek runs year round. The complex features a seasonal pool and year round sauna and hot tub. Also a club house with a pool table, ping-pong, foosball and a fitness area. It's an easy walk to the historical town o
Fourth Sister Retreat
2 Bedrooms
$118 - $811 / per night
2
bedrooms
2
baths
6
guests
4.9
(13)
Welcome to our charming vacation rental nestled in the beautiful neighborhood of Tollgate in Sisters, Oregon. This delightful 3-bedroom, 2-bathroom house offers the perfect retreat for your next getaway. With comfortable sleeping arrangements including 2 queen beds, two twin beds, a sleeper sofa, and a queen air mattress, there's plenty of space to
Peters Cabin
3 Bedrooms
$108 - $445 / per night
3
bedrooms
2
baths
8
guests
5
(3)
Escape to your own private paradise at this stunning vacation rental in Sisters, Oregon. This beautiful 40-acre ranch is bordered by 3,500 acres of BLM land, providing you with endless opportunities to explore the great outdoors. With 5 bedrooms and 3 full bathrooms, this home can accommodate up to 10 guests comfortably.Inside, you'll find that the
Jumping Juniper Ranch Main House
5 Bedrooms
$328 - $1,354 / per night
5
bedrooms
3
baths
10
guests
Escape to the beauty of central Oregon and stay in our charming 3-bedroom, 2 full bath, 2-story vacation rental nestled in the serene Tollgate community of Sisters, Oregon. Perfect for families, friends, or couples seeking a relaxing getaway, this cozy retreat offers a range of amenities that promise to elevate your vacation experience.Step inside
Martingale Lodge
3 Bedrooms
$113 - $689 / per night
3
bedrooms
2
baths
8
guests
5
(4)
Let us welcome you to, Magical Sisters Retreat. A calm and relaxing 2 bedroom 2 bath condo located in the Pine Meadow Village neighborhood. With easy access to Highway 20 and a short walk to downtown; you will be positioned perfectly to enjoy all that Sisters Oregon has to offer. When you enter you will be greeted by an open, bright and inviting s
Magical Sisters Retreat
2 Bedrooms
$94 - $514 / per night
2
bedrooms
2
baths
4
guests
5
(9)
This Beautiful home has room for the whole family, extended family, and friends. Located in the neighborhood of Tollgate, you are surrounded by acres of National Forest, have access to the seasonal pool, biking paths, a tennis court, and a basketball court. Making memories is easy in this spacious home. Imagine relaxing in the hot tub with your
Wagon Wheel Home
5 Bedrooms
$124 - $955 / per night
5
bedrooms
3
baths
10
guests
5
(2)
We would like to welcome you to this Deschutes River View Condo located in the beautiful community of Eagle Crest, a 5-Star Resort. This uniquely positioned condo is located on a dead-end street giving you additional privacy and avoiding through traffic.When entering the condo, you will be greeted by an open space with plenty of natural light, roo
Deschutes River View Eagle Crest
3 Bedrooms
$174 - $526 / per night
3
bedrooms
2
baths
6
guests
4.6
(6)
Sitting just off from the historical downtown of Sisters, nestled in the trees, this delightful condo offers a perfect blend of comfort and entertainment, making it an ideal retreat for all. When you enter this upstairs condo you will immediately notice the clean and cozy feel it provides. From the decor to the furniture to the wood fireplace, it a
Fourth Sisters Bliss
2 Bedrooms
$90 - $507 / per night
2
bedrooms
2
baths
4
guests
5
(2)
Park the car and walk or bike to everything in town, mountain views, and A/C. Come to Sisters and take in the views of four mountains and a pond w/seasonal fountain from this condo. It is on the west edge of Sisters and only a few blocks to the heart of downtown Sisters to shop, dine, browse. Year-round spa and seasonal pool privileges are included
Riley`s Mountain View
2 Bedrooms
$118 - $643 / per night
2
bedrooms
2
baths
6
guests
4.9
(21)
Escape to this charming and budget-friendly vacation retreat, perfect for two couples or a small family. With two inviting bedrooms and two bathrooms, this cozy haven comfortably accommodates up to six guests.Nestled just a stone's throw away, you'll discover the Tollgate seasonal pool, a tennis court, basketball court, a delightful children's play
The Sisters Moose
3 Bedrooms
$98 - $459 / per night
2
bedrooms
2
baths
6
guests
4.9
(23)
Welcome to Fairway View, a distinctive residence located on the 7th hole of Big Meadow golf course, in the prestigious Black Butte Ranch community.Inside, this three story home boasts generously sized living areas, perfect for family gatherings and entertaining. On the second level you will find a well-equipped kitchen featuring modern appliances,
Fairway View
5 Bedrooms
$171 - $1,130 / per night
5
bedrooms
11
guests
4.7
(9)
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