Cottage holiday rentals in Bend

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Top-rated cottage rentals in Bend

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Guest favourite

Cottage

4.94 out of 5 average rating, 269 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.

Guest favourite

Cottage

4.96 out of 5 average rating, 25 reviews

Cottage Live/Play in the Heart of Downtown Sisters

Our Cottage is quiet, clean and close to the center of downtown Sisters with its boutiques and restaurants less than two blocks from your door. No car needed. And even being close to everything provides open vistas of the Three Sisters Mountain range, expansive views of ranch life within a few steps and a community known for special events. Let your inner-west shine. (NOTE: We cancelled Airbnb in 2016 & stayed with VRBO. We're back. Have had 5 star reviews for 12 years with VRBO.)

Guest favourite

Cottage

4.98 out of 5 average rating, 100 reviews

The Tumalo House

The Tumalo House is located just north of Bend and is situated between Tumalo Cider and Bend Cider. Just across the street from The Bite, the local hang out, this fully renovated 1940's farm house offers 2 bedrooms, sofa bed and 1 bath, and outdoor space with a gas fire pit. This cozy find is only steps from the Deschutes river, 30 minutes from Mt. Bachelor and minutes from Downtown Bend and The Shops at the Old Mill. No matter what brings you here, this home will make you want to stay!

Guest favourite

Cottage

4.98 out of 5 average rating, 146 reviews

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, NATURE'S BEAUTY IS 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.

Guest favourite

Cottage

4.95 out of 5 average rating, 114 reviews

The Mill Cottage - a perfectly located retreat

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.

Guest favourite

Cottage

4.99 out of 5 average rating, 117 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.

Guest favourite

Cottage

4.95 out of 5 average rating, 402 reviews

Vintage Pink Hot Tub✓ Walkable✓

$120.00 clean fee 3 plus nights $50 per pet fee 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. The original charm was painstakingly preserved, with original claw foot tub, and with your comfort in mind, modern conveniences like Hot Tub, Gas fireplace, Dishwasher, W/D. Easily accessible, centrally located urban setting on a main street.

Guest favourite

Cottage

4.94 out of 5 average rating, 224 reviews

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.

Guest favourite

Cottage

4.97 out of 5 average rating, 118 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

Superhost

Cottage

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.

Guest favourite

Cottage

4.97 out of 5 average rating, 107 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.

Guest favourite

Cottage

4.95 out of 5 average rating, 325 reviews

Adorable West Side Cottage, Great Location!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed. Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown