Vacation Rentals
40 properties available
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 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
Welcome to our charming upstairs condo nestled in the beautiful town of Sisters, Oregon. This delightful vacation rental offers a perfect blend of comfort and entertainment, making it an ideal retreat for families or groups of friends. As you step inside, you'll be greeted by a warm and inviting living space adorned with a cozy fireplace, creating
Hiker’s Hideaway – Modern Retreat in Sisters, OregonEscape to the beauty of Central Oregon at Hiker’s Hideaway, a stylish and comfortable 3-bedroom townhouse designed for adventure, relaxation, and making memories together.Located in the peaceful Cold Springs neighborhood just minutes from downtown Sisters, this modern mountain retreat is the perfe
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
HIGHLIGHTS Access to the Pine Meadow Village clubhouse with a seasonal pool and year-round hot tubOpen-concept living area with a gas-burning fireplace and comfortable seatingPrivate balcony with seating, pond and mountain viewsFree parking on premises and self check-inWelcome to our 2-bedroom, 2-bath condo in Pine Meadow Village. It’s a comfortabl
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
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
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 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
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
We would like to welcome you to The Quails Nest. This charming and whimsical home is in the heart of Sisters Oregon on a quiet neighborhood street.When entering the home, you will notice a welcoming entry way encouraging you to enter relax mode.To the left is the downstairs half bathroom, and as you proceed into the home you are greeted by an open
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