Early Bird Booking
Early Bird Booking Promo – Plan Ahead & Save 10%
Planning your getaway early has its perks! Book your stay 90 days or more before your arrival date and enjoy 10% off your reservation. It’s the perfect way to lock in your favorite vacation rental, secure the best dates, and save on your upcoming trip.
This offer is valid on new bookings only and cannot be combined with other promotions or discounts.
Ready to start planning your next escape?
📞 Call 877.632.7007 to book your stay and claim your Early Bird savings!
50 properties available
Welcome to The Branches on Jefferson, a unique opportunity to reserve an entire building in the heart of Sisters. Ideal for family gatherings, friend groups, wedding parties, and event travelers, this property combines togetherness with privacy—something rarely found in downtown locations.With three separate apartments under one roof, everyone can
Sisters Dream Inn vacation rental is the quintessential retreat for your Central Oregon vacation. This beautiful, charming and authentic 2-story, 2 bedroom (one is in the upstairs loft) and 1.5 bath pine log cabin is situated on a two acre parcel of pine forest land in a very quiet neighborhood set into the Deschutes National Forest only a couple o
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
Welcome to Branch A – Aspen Suite, a thoughtfully designed studio just a couple of blocks from Sisters Coffee and an easy walk to downtown shops, dining, and local events. This inviting space comfortably sleeps up to four guests with a queen bed and Murphy bed, making it ideal for couples, small families, or friends traveling together.The studio fe
Welcome to our charming ground level condo located in the heart of Sisters, Oregon. This cozy and inviting two-bedroom, two-bathroom vacation rental is the perfect place to unwind and enjoy all that this beautiful town has to offer. As you step inside, you'll be greeted by a spacious and tastefully decorated living area with comfortable seating, pe
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
Welcome to Your Black Butte Ranch GetawaySet right on the golf course, this spacious 3-story retreat offers the perfect blend of privacy, comfort, and classic cabin charm. Ideal for multiple families or group getaways, this home is designed to give everyone space to spread out—while still coming together to create memorable moments.Why Guests Love
Welcome to Jacob’s Ladder, a warm and welcoming family retreat in the heart of Black Butte Ranch, perfectly located just a short walk from Glaze Meadow Pool, sports courts, playgrounds, and trails. This spacious 3-bedroom, 2.5-bath home has been a longtime favorite for families and multi-family groups thanks to its thoughtful layout, peaceful setti
Previously known as Sister Home Upper, Sisters Retreat Upper is new and modern, bright and cheery, with all you need for comfortable lodging with short walk to downtown and plenty of parking.If you plan to be out and about most of the time you are visiting Sisters, this place is perfect and comfortable for up to 5 people.Park the car, close to ever
Welcome to Pine Rest, a bright and comfortable two-bedroom, two-bathroom condo in the quiet Pine Meadow Village neighborhood. Its thoughtful bedroom layout works well for families, couples, or friends traveling together, while its upstairs location offers a peaceful place to unwind after exploring Sisters and Central Oregon.**The Space**Located on
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
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
Tell us what you're looking for and someone will contact you with available options.