Cottage holiday rentals in Sisters

4.93 out of 5 average rating, 282 reviews

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

Located in the heart of NW Bend in the middle of it all! A short walk to great restaurants + pubs, the river, Amphitheater, Downtown, 3 Parks, The Old Mill -but on a nice quiet street. Well worth the price, it sleeps a comfortable 4 and a cozy 6 with a comfty Queen bed in one room, and pine bunk bed in other room (full bed on bottom and top with cozy mattresses). Large enclosed yard for the pets and patio with Hot tub! The home is well stocked, tastefully furnished with high quality bedding.

4.95 out of 5 average rating, 418 reviews

Vintage Pink Hot Tub✓ Walkable✓

NOTE: Thru June ongoing road construction is scheduled on Portland Ave. Please read Other Things to Note below before booking :-) Our 105 year-old lovingly restored 1920 cottage is 3 blocks from First Street River Rapids, 25 minutes to Bachelor & 10 minute walk to Town. Centrally located urban setting on a main street. Step back in time, the original charm was painstakingly preserved, with original claw foot bathtub, wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

4.92 out of 5 average rating, 122 reviews

Cottage in La Pine

“Peaceful Pines Cottage” 2+ acres near Mt. Bach

Peaceful Pines Cottage is a newly renovated PET FRIENDLY remote cottage located in Central Oregon. Perfect for ski trips at Mt. Bachelor & Willamette Ski Resort! This 3 bedroom / 2 full bathroom home is on 2.25 acres of fully fenced-in land that backs up to public BLM land for you to explore.. Driving distance to downtown La Pine, Bend, PCT trails, Crater Lake National Park, lakes + much more! This is the perfect home for a gathering with loved ones or a relaxing weekend for yourself.

4.98 out of 5 average rating, 158 reviews

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna

IMAGINE WALKING A FEW MINUTES TO THE HEART OF DOWNTOWN, YET STILL NESTLED AMONGST OLD-GROWTH PONDEROSA PINES IN A SERENE SETTING, NATURES BEAUTY ALL AROUND TO TAKE IN. Various restaurants, local festivals, parks, hiking and biking trailheads, Fives Pines Resort and Spa, Creekside campground, and an athletic center are moments away. Minutes drive to Hoodoo Mountain, Black Butte Resorts, Aspen Golf Course, and Eagle Airport. Extensive free off-road parking, RV parking, and internet.

4.94 out of 5 average rating, 117 reviews

Cottage in Old Bend

Two Bedroom Charmer with Hot Tub

The Mill House cottage is one of three historic cottages on this property. It is located in the heart of Bend between the historic downtown and desirable Old Mill district. There is no better location than this one, just steps from Columbia river park and walking distance from the amphitheater, 10 Barrel Brewery, Good Life Brewery, Jackson's Corner and Active Culture. We offer complimentary bikes making it easy for you to zip downtown for your morning coffee or evening happy hour.

4.99 out of 5 average rating, 119 reviews

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

4.94 out of 5 average rating, 233 reviews

Cottage in Old Bend

Historic Downtown, Private Hot Tub, High Demand

This amazing little downtown cottage provides all the comforts of home with the freedoms of vacationing. You cannot find a better location than The Autumn Cottage! It is located on a quiet little street, yet it is just one block from the historic downtown area. It has been lovingly designed to offer guests the full flavor of Bend, with many modern amenities paired with classic charm to make your Bend visit exceptional.

4.97 out of 5 average rating, 119 reviews

Exceptional Downtown Cottage-Level II EV charger

24 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Exceptional 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. These significant investments keep the Cottage fresh and like it was brand new. City of Bend Short Term Rental Operating License: STR-20-0285

4.92 out of 5 average rating, 163 reviews

Amazing Location! | Charming, Cozy Cottage

There is no better way to explore Bend than in this vibrant, centrally located, popular neighborhood in the heart of Bend. This charming cottage will have you feeling right at home during your visit. Enjoy a spacious backyard area with a gas fire pit, a fully equipped kitchen, comfortable communal areas for lounging and dining, a bathroom downstairs, one private bedroom downstairs and another upstairs.

4.97 out of 5 average rating, 117 reviews

Cottage in Sunriver

Cozy Home w/River Access, Hot Tub, 5min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.

4.97 out of 5 average rating, 112 reviews

River Camp House

The perfect getaway for the outdoor enthusiast and for local entertainment in this ultra clean Bend home. Hop on the trails from the doorstep of this riverside home. Rustic tables, wooden floors, and a central fire place lend to the warm, cabin ambiance. Relax on the patio by the fire pit perfect for roasting marshmallows after a full day on the slopes.