Vacation Rentals
42 properties available
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! This upstairs condo has one
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
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
Cozy Loft Retreat | Walk to Downtown SistersWelcome to Pine Street Loft, a charming loft-style retreat in the heart of Sisters, Oregon. Thoughtfully designed for couples, solo travelers, and small families, this inviting getaway combines modern comfort with the relaxed pace of a mountain town.Located just a short walk from downtown Sisters, you'll
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 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
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
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
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
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
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
Newly remodeled 2 bedroom 2 bath home just outside of Sisters. Located on a private, wooded, one acre lot in Crossroads.Your dog will enjoy this vacation as well with a fully fenced front yard. This is the enchanted area of the explorers Lewis and Clark, offering miles and miles of rivers, lakes, forest, and stunning mountain peaks.For the golfer
Tell us what you're looking for and someone will contact you with available options.