Cottage vacation rentals in Bend

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Top-rated cottage rentals in Bend

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Guest favorite

Cottage in Bend

4.94 out of 5 average rating, 236 reviews

5 star! 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.

Aug 22 – 29

G$71,878 GYD per night

Guest favorite

Cottage in Terrebonne

4.9 out of 5 average rating, 260 reviews

Quiet central Oregon desert retreat with a view!

Bright and cheery cottage on five acres with a view! Bathrooms completely renovated in 2019 with tile and modern barn decor. Premium linens and duvets. Fully stocked kitchen with Nespresso machine. Gas BBQ on the deck! Relax in this extraordinary high desert setting or hike right out your front door. Located in a rural area 50 minutes north of Bend, between the Deschutes and Crooked Rivers, you will have access to climbing, fishing, kayaking. Come visit the craft breweries in nearby Redmond!

Apr 23 – 30

G$29,913 GYD per night

Guest favorite

Cottage in Sisters

4.98 out of 5 average rating, 103 reviews

Walk Downtown! Family&Friend Retreat/Sauna

Imagine walking a few minutes to the heart of downtown, yet still nestled amongst old-growth pine in a serene setting. Minutes walk away from a variety of restaurants, local festivals, parks, hiking, and biking trailheads, Fives Pines Resort, Creekside campground. Minutes drive to Hoodoo Mountain, Black Butte Resorts, Aspen golf course. While relaxing in the evenings, enjoy the sound of Whychus Creek flowing in the distance. Extensive free off-road parking and RV parking, high-speed internet.

Oct 17 – 24

G$50,169 GYD per night

Superhost

Cottage in Bend

4.89 out of 5 average rating, 279 reviews

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

Apr 8 – 15

G$38,769 GYD per night

Guest favorite

Cottage in Bend

4.95 out of 5 average rating, 209 reviews

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage perfectly embodies the spirit of Bend. This charming two bedroom, one bathroom vacation home is ideal for those Bend explorers who wish to be in the heart of it all. This house is located on a vibrant and eclectic street, situated just two blocks from downtown Bend. You are just a short stroll to all the superb dining, infamous breweries, art galleries, and festivals that make our town so unique.

Aug 17 – 24

G$86,436 GYD per night

Guest favorite

Cottage in Bend

5.0 out of 5 average rating, 93 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.

Jun 4 – 11

G$51,163 GYD per night

Guest favorite

Cottage in Bend

4.92 out of 5 average rating, 159 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.

Aug 7 – 14

G$74,437 GYD per night

Superhost

Cottage in Bend

4.77 out of 5 average rating, 121 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!

Jul 30 – Aug 6

G$31,600 GYD per night

Guest favorite

Cottage in Sunriver

4.95 out of 5 average rating, 39 reviews

Cozy Charmer with River Access, 5mins 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.

Oct 15 – 22

G$34,987 GYD per night

Guest favorite

Cottage in Bend

4.94 out of 5 average rating, 300 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.

Oct 6 – 13

G$48,752 GYD per night

Guest favorite

Cottage in Bend

4.97 out of 5 average rating, 77 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.

Sep 23 – 30

G$39,671 GYD per night

Superhost

Cottage in Bend

4.89 out of 5 average rating, 102 reviews

The Sparrow Cottage in the Old Mill

The Sparrow House is located in the heart of Bend between the historic downtown and desirable Old Mill district. It is within walking distance to just about everything you could want from the grocery store to some of the best restaurants in town (check out our guidebook).

Oct 13 – 20

G$45,775 GYD per night