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.


Properties Available 13 properties available
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
$125 - $895 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (2)
Beautiful custom built condo on ground level in desirable Pine Meadow Village with exceptional outdoor space. Spacious, 1720 sq. ft. of living space, the clubhouse, with seasonal swimming pool and spa, is conveniently just across the street from this very spacious property. Walking distance to eateries, shopping, and all Sisters has to offer.Featur
Hot HOT 36
Mountain Sage
3 Bedrooms Pet Friendly
$125 - $668 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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
Hot HOT 17
Riley`s Mountain View
2 Bedrooms Pet Friendly
$119 - $480 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (17)
Each bedroom comes with it's own sink and toilet and bedrooms 4 and 5 share a shower as do bedrooms 2 and 3. The master has its own bathroom and shower. Please note, Black Butte Ranch charges $9.00** per person per day forthose 7 years old and up. These are fees for maintaining the pools,bike paths, and other recreational activities. When you arriv
Hot HOT 14
Fairway View
5 Bedrooms
$145 - $860 / per night
Bedrooms 5 bedrooms
Guests 11 guests
This home is a short walk to Glaze Meadow Pool, tennis courts, playground, pickleball, and bike/ski rental shop. In the summer months, you can walk up to the Glaze Meadow pool cafe for a coffee or their famous cinnamon rolls. The house has 3 bedrooms, 2 1/2 bathrooms plus a shower room off the garage. The master has a king size bed with ensuite tub
Jacobs Ladder - Black Butte Ranch
3 Bedrooms
$119 - $646 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
The 4th Sister Lodge 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 of Sisters and its many artisanal shops, art galleries, c
Hot HOT 15
Fourth Sister Retreat
2 Bedrooms
$160 - $414 / per night
Bedrooms 2 bedrooms
Guests 6 guests
Welcome to our charming vacation rental in the picturesque Tollgate neighborhood of Sisters, Oregon. This delightful getaway offers a comfortable and spacious retreat for your family or group of friends, boasting four bedrooms, two bathrooms, and a variety of amenities to make your stay memorable.As you step inside, you'll be greeted by a warm and
Hot HOT 12
Halter Garden Home
3 Bedrooms Pet Friendly
$129 - $465 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
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
$95 - $390 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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
Hot HOT 25
Lariat House
3 Bedrooms Pet Friendly
$129 - $546 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Inviting and sunny, the wall of windows and vaulted ceilings make this condo a delight to be in, in the quaint Pine Meadow Village neighborhood. Enjoy everything Sisters has to offer, walk to everything in town, hang out at the pool (seasonal), or soak in the hot tub. There are tennis courts just a couple of blocks too!Nicely and fully furnished an
Hot HOT 11
The Three Sisters
2 Bedrooms
$65 - $343 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (25)
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
Hot HOT 24
The Sisters Moose
3 Bedrooms
$99 - $259 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (19)
Experience a Tranquil Getaway at our 2-Bedroom Condo in Pine Meadow Village, Sisters OregonWelcome to our charming 2-bedroom, 2 full bath vacation rental condo located in the peaceful Pine Meadow Village neighborhood of Sisters Oregon. This delightful vacation retreat offers a comfortable and relaxing experience for up to 6 guests.Upon entering, yo
Hot HOT 33
Big Mountain View Condo
2 Bedrooms Pet Friendly
$119 - $663 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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