Cottage holiday rentals in Bend

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Top-rated cottage rentals in Bend

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Guest favourite

Cottage in Bend

4.93 out of 5 average rating, 247 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 in Terrebonne

4.91 out of 5 average rating, 272 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!

Superhost

Cottage in Bend

4.9 out of 5 average rating, 293 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.

Guest favourite

Cottage in Redmond

5 out of 5 average rating, 22 reviews

The West Minister Square Cottage

Come stay in fun, historic downtown Redmond just steps away from quaint shops, delicious restaurants, breweries, and food trucks! This cottage is a stand-alone building on a large lot that used to house clergy for the first church built in town in 1912. This cozy retreat is quiet, private, and peaceful. It has been lovingly restored top to bottom, and the interior is beautifully decorated to meet your every hope for comfort and convenience while you have your adventure in Central Oregon.

Guest favourite

Cottage in Old Bend

4.95 out of 5 average rating, 219 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.

Guest favourite

Cottage in Redmond

4.91 out of 5 average rating, 23 reviews

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

Guest favourite

Cottage in Bend

4.99 out of 5 average rating, 104 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 in Sisters

4.98 out of 5 average rating, 120 reviews

Walk mins to 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 quiet setting. Variety of restaurants, local festivals, parks, hiking, biking trailheads, Fives Pines Resort, and Creekside campground. Minutes drive to Hoodoo Mountain, Black Butte Resorts, Aspen Golf Course and Eagle Airport While relaxing in the evenings, enjoy the sound of Whychus Creek flowing in the distance. Extensive free off-road parking, RV parking, and internet

Superhost

Cottage in Bend

4.92 out of 5 average rating, 160 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 in Sunriver

4.96 out of 5 average rating, 57 reviews

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.

Guest favourite

Cottage in Bend

4.94 out of 5 average rating, 303 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 in Bend

4.98 out of 5 average rating, 86 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.