Tollgate Rentals
From $606 per night (USD)VRBO
STAY IN SISTERS! PICKLEBALL, SWIM, TENNIS, GOLF, SHOP, BIKE, HIKE, DINE & MORE!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautifully hand scribed log home is the perfect vacation destination for your small group or family. It offers the ...
From $606 per night (USD)VRBO
From $225 per night (USD)Expedia
Unique Private Cabin in the Pines in Sisters! Clean & Cozy!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and enjoy our cozy cabin nestled in the Ponderosa pines in Tollgate, 2 miles west of Sisters, for a peaceful relaxi ...
From $225 per night (USD)Expedia
From $495 per night (USD)VRBO
Forest mountain retreat with resort-style amenities and minutes from Sisters
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come relax in a cozy one-story home among lush Ponderosa Pine trees bordering the Deschutes National Forest and only two ...
From $495 per night (USD)VRBO
From $762 per night (USD)Expedia
Modern Tollgate Mountain Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your perfect mountain escape in Tollgate, just outside Sisters, Oregon! This beautifully updated 4-bedroom, 2 ...
From $762 per night (USD)Expedia
From $395 per night (USD)VRBO
Ponderosa Pines *Cabin*, Sisters OR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tranquil Forest Retreat in Sisters – 2BR/2BA House, Hot Tub & Outdoor Living Welcome to your perfect Central Oregon get ...
From $395 per night (USD)VRBO
From $331 per night (USD)Expedia
Home with a private hot tub, shared pool, & National Forest at your backdoor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dunn Valley The Space: Treat your family to a fantastic modern vacation retreat with a private backyard ho ...
From $331 per night (USD)Expedia
From $287 per night (USD)VRBO
Family-Friendly Home with Fireplaces, Firepit, Gas Grill, Free WiFi, Central AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Retreat in the Pines The Space: This lovely, modern home boasts all the essential comforts to ensure a per ...
From $287 per night (USD)VRBO
From $246 per night (USD)Expedia
Rustic Cabin Rental near Hoodoo Ski Area and the Deschutes River in Sisters, Oregon
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
This rustic cabin rental near Sisters, Oregon, can accommodate up to nine guests at a time, making it ideal for groups o ...
From $246 per night (USD)Expedia
From $487 per night (USD)VRBO
HOT TUB, Dog Friendly, Steps from pickleball/pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
What you’ll love about our Sisters retreat: - Steps from the Tollgate community pool and pickleball courts - Private sal ...
From $487 per night (USD)VRBO
From $473 per night (USD)Expedia
The Nest | Private Guest Suite Near DT Sisters
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Nest Escape to The Nest, a bright and spacious private guest suite just minutes from downtown Sisters. W ...
From $473 per night (USD)Expedia
From $653 per night (USD)VRBO
Cozy 3 bedroom, 3 bathroom, Log Home, PET FRIENDLY, Tollgate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Tollgate! Just a short drive from Sisters, this cute and quiet neighborhood is the perfect spot for your fami ...
From $653 per night (USD)VRBO
From $571 per night (USD)Expedia
Ponderosa Pines *Cabin + Casita*, Sisters OR
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tranquil Forest Retreat in Sisters – 3BR/3BA House + Casita, Hot Tub & Outdoor Living Welcome to your perfect Central O ...
From $571 per night (USD)Expedia
From $312 per night (USD)VRBO
Enjoy Our Family Friendly Home In Tollgate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You've got to see this place. We have a whole wall of windows facing South with frequent small herds of deer visiting. A ...
From $312 per night (USD)VRBO
From $416 per night (USD)VRBO
House in the Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our Woodsy Escape with 3 bedrooms and 2 bathrooms to accommodate up to 6 adults and children. The interior includ ...
From $416 per night (USD)VRBO
From $310 per night (USD)VRBO
Great Mountain View in the heart of Central Oregon
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on 3/4 acre in Toll Gate subdivision with pool, this home has a beautiful view of the Three Sisters from the liv ...
From $310 per night (USD)VRBO
From $430 per night (USD)Expedia
Modern Tollgate Home - HOT TUB, Half Acre Lot
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you ...
From $430 per night (USD)Expedia
From $444 per night (USD)VRBO
Home nestled in the forest just outside Sisters
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sit back and relax. If you love the outdoors and sitting in a pine tree forest, you'll love this. It's a short walk on a ...
From $444 per night (USD)VRBO
From $397 per night (USD)Expedia
Cozy Tollgate Cabin Near Trails + Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Nestled in the friendly Tollgate community just minutes from downtown Sisters, Oregon, The Sisters Moose is the perfect ...
From $397 per night (USD)Expedia
From $534 per night (USD)VRBO
Martingale Lodge Cozy 3 bdrm, 2 bath, Sisters Oregon, private hot tub, backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the beauty of central Oregon and stay in our charming 3-bedroom, 2 full bath, 2-story vacation rental nestled ...
From $534 per night (USD)VRBO
From $365 per night (USD)Expedia
Peters Cabin Cozy Retreat in Sisters Tollgate Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming vacation rental nestled in the beautiful neighborhood of Tollgate in Sisters, Oregon. This delig ...
From $365 per night (USD)Expedia
From $479 per night (USD)VRBO
Stunning Single level Home, Hot Tub, Fenced Yard, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Sisters Basecamp This stunning 5 bedroom, 3 bath home is the perfect getaway for guests looking to mix a little relax ...
From $479 per night (USD)VRBO
From $381 per night (USD)Expedia
Sweet Retreat Cozy Cabin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dreamy getaway in the mountains near Sisters, Oregon. You will have use of the entire cabin. This cabin is completely re ...
From $381 per night (USD)Expedia
From $326 per night (USD)VRBO
Fantastic Forested Escape, *Pet Friendly*, Open Layout, Fireplace, Huge Deck, 3 Miles to Sisters
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled in the towering pines of the Deschutes National Forest, You will find a modern cabin retreat within the Tollgate ...
From $326 per night (USD)VRBO
From $361 per night (USD)Expedia
Cozy Hideaway w/outdoor living and hot tub! Close to skiing and hiking.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax or work from our comfortable and Cozy Hideaway, just a quick bike ride or drive to downtown Sisters. Inhale the pi ...
From $361 per night (USD)Expedia
From $693 per night (USD)VRBO
House+ADU+GameRoom+Jacuzzi+Pool+Fire pit+Loft
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Get ready to relax in this 6-bedroom house in Sisters. This wonderful property boasts 2 king beds, 1 bunk bed, 1 queen b ...
From $693 per night (USD)VRBO
From $397 per night (USD)Expedia
Dog-Friendly Retreat w/ Hot Tub & Forest Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to the Talking Pines cabin - your perfect getaway in Sisters, Oregon. This beautifully maintained home blends mod ...
From $397 per night (USD)Expedia
From $325 per night (USD)VRBO
Wooden A-Frame Cabin Nestled in the Tall Pines
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful cabin in the woods. 'Your Sisters Cabin' is geared towards fun and relaxati ...
From $325 per night (USD)VRBO
From $456 per night (USD)Expedia
Lariat House Dog-Friendly Retreat in Sisters
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming and dog-friendly vacation rental nestled in the beautiful Tollgate community of Sisters, Oregon. ...
From $456 per night (USD)Expedia
From $393 per night (USD)VRBO
Family-Friendly, Modern Home with Extra Large Hot Tub with EV Charger
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come explore all that Central Oregon has to offer and relax in this beautiful, family friendly home. This home has moder ...
From $393 per night (USD)VRBO
From $326 per night (USD)Expedia
Hot Tub, Fire Pit, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Step into the warm embrace of 🌲 Cascadia Cottage, your cozy retreat nestled in the heart of scenic Sisters, Oregon. Tho ...
From $326 per night (USD)Expedia
From $408 per night (USD)VRBO
1-acre retreat with firepits, wraparound porch & a relaxing 6-person hot tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your peaceful 1-acre country retreat, a bright and inviting home designed for comfort in every season. Relax ...
From $408 per night (USD)VRBO
From $350 per night (USD)Expedia
Adventure Basecamp in Sisters | Fireplace + Garage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hiker’s Hideaway – Modern Retreat in Sisters, Oregon Escape to the beauty of Central Oregon at Hiker’s Hideaway, a styli ...
From $350 per night (USD)Expedia
From $545 per night (USD)VRBO
House + Bonus Room, HOT TUB, Huge Yard, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This modern and family friendly home is nestled among mature pine trees on a fully landscaped half acre lot with a hot t ...
From $545 per night (USD)VRBO
From $445 per night (USD)Expedia
Juniper & Pine • Barrel Sauna + Hot Tub • Sisters, Oregon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to Juniper & Pine, a peaceful 3-bedroom, 2.5-bath cabin nestled in a quiet neighborhood inside the Deschutes Nati ...
From $445 per night (USD)Expedia
From $426 per night (USD)VRBO
2 min to Downtown Sisters, Family Friendly, XBOX, Game Rm, Outdoor Patio w/ BBQ,
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Stagecoach Manor in Sisters, Oregon Welcome to Stagecoach Manor ~ Your western-themed retreat in the heart of Sisters! ...
From $426 per night (USD)VRBO