Vacation Rentals
38 properties available
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
Cozy Studio Retreat | Walk to Downtown SistersWelcome to Jefferson Hideaway, a cozy and thoughtfully designed studio retreat tucked away in a quiet neighborhood just steps from downtown Sisters.Whether you're visiting for a romantic getaway, a cycling adventure, a hiking trip, or a relaxing weekend exploring Central Oregon, this private hideaway of
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
Your Black Butte Ranch Family EscapeTucked among the towering pines of beautiful Black Butte Ranch, this cozy and welcoming retreat is the perfect place to slow down, reconnect, and experience the best of Central Oregon.Whether you're planning summer adventures, family bike rides, winter ski days, or peaceful mornings surrounded by nature, this hom
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
Ponderosa Sunset Retreat is a gorgeous, 2 bedroom 2 bath condo located fountain side in the Pine Meadow Village community moments away from Sisters city center. Accommodating up to 6, it's perfect for two small families, a couples trip, or a friends getaway! The spaceWe can't wait to welcome you to The Ponderosa Sunset Retreat! Our home is locate
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
Escape to the serene beauty of Whychus Canyon, a perfect destination for a romantic getaway or peaceful retreat. This newly built, 3-bedroom, 2-bathroom home offers breathtaking canyon views and an idyllic location to relax and reconnect with nature.Wake up to spectacular sunrises over the canyon, enjoy sunlight streaming through a south-facing wal
Welcome to your own private oasis at this stunning yurt vacation rental located on a 40-acre ranch. With a full bathroom complete with a soaking tub and a fully equipped kitchen, this yurt offers the perfect romantic escape for a couple.Inside the yurt, you'll find a cozy and intimate space, with a comfortable queen-sized bed perfect for two people
Tucked away on 3 peaceful acres with jaw-dropping views of the Three Sisters and Broken Top, Vista View Retreat is your perfect home base for adventure, rest, and everything in between. Just a short 10-minute drive from the heart of downtown Sisters, this 4-bedroom, 2-bathroom home comfortably sleeps up to 8 guests and welcomes dogs, making it idea
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
A True Central Oregon EscapeWelcome to Jumping Juniper Ranch. Your own private oasis just outside Sisters. With 40 acres to explore and direct access to 3,500+ acres of BLM land, this is the perfect place to unplug, spread out, and reconnect with the people you’re traveling with.Whether you're planning a family vacation, friends getaway, or a quiet
Tell us what you're looking for and someone will contact you with available options.