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

4.93 out of 5 average rating, 256 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

4.94 out of 5 average rating, 396 reviews

Vintage Pink Hot Tub✓ Walkable✓

***Monthly Discount*** 30 day rental discount 7 night discount $120.00 clean fee 3 plus nights $50 per pet fee Our 104 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

4.96 out of 5 average rating, 24 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 in Sisters

4.98 out of 5 average rating, 137 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, 113 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.

Superhost

Cottage in Bend

4.78 out of 5 average rating, 134 reviews

New mid century cottage w/ hot tub & view

Welcome to Central Oregon! Tumalo is a quaint farming community 15 minutes from Bend, Redmond, and Sisters. It's the most central location to incredible rivers, climbing, hiking, skiing, biking, and all other activities you enjoy. The exterior is in a constant state of improvement! Depending on when you come, you may see piles of dirt and rock, or new vegetation, mulch. Update....we now have AC! And we have a king bed instead of a queen!!!

Guest favourite

Cottage

4.93 out of 5 average rating, 214 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

23 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

Guest favourite

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

4.95 out of 5 average rating, 313 reviews

Adorable West Side Cottage, Great Location!

My adorable and extremely comfortable 1 bedroom, 2 bath, w/ bonus room cottage is perfect for your getaway. Very comfortable house, Nectar Premier Copper Hybrid Mattress, pet-friendly, Apple TV, great porch, and fenced-in yard with firepit. Walk to Newport Market, Backporch Coffee, Chow, Spork, etc. Only five blocks from downtown. Off-street parking for two cars or can fit a large van.

Guest favourite

Cottage

4.98 out of 5 average rating, 103 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.