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76 Best cottages in Bend, OR
Bend, OR
11/08 – 11/10
$726/nighttotal: $1452 (2 )
2 Units Minutes To Downtown Bend Hot Tub 1208 Skyline Ranch By Avantstay
1 2
cottage , Bend
This cottage is located in Bend's Summit West district, under 1 mile from Discovery Park Off-Leash Area and Central Oregon Community College, and within 2 miles of Westside Church and Overturf Butte Off-Leash Area. This pet-friendly accommodation offers air conditioning, free WiFi, a full kitchen with a microwave and refrigerator, and a private balcony, with barbecue grills available for guest use.
Bend, OR
11/08 – 11/10
$711/nighttotal: $1422 (2 )
2 Units Minutes To Old Bend Deck + Hot Tub 1216 Skyline Ranch By Avantstay
1 2
cottage , Bend
This cottage is located in Summit West, Bend, offering easy access to attractions such as Discovery Park Off-Leash Area and Central Oregon Community College, both under 1 mile away, and Overturf Butte Off-Leash Area and Westside Church, both within 2 miles. This pet-friendly rental features a full kitchen with a microwave and dishwasher, air conditioning, a balcony, and on-site parking, with free WiFi available in public areas.
Bend, OR
11/08 – 11/10
$511/nighttotal: $1022 (2 )
Updated Farmhouse W/ Deck On Central Oregon Canal!
1 2
cottage , Bend
This charming cottage is located in Bend, Oregon, just 2.6 miles from Bend Rock Gym and within 6 miles of St. Charles Bend and Pilot Butte State Park. It features a fully equipped kitchen with a microwave and dishwasher, 2 bathrooms, and a TV. Guests can enjoy free self-parking, free WiFi in public areas, and barbecue grills. The cottage is pet-friendly and has air conditioning for your comfort.
Bend, OR
11/08 – 11/10
$368/nighttotal: $736 (2 )
Ponderosa Pines By Avantstay Gorgeous Deck, 10 Mins From Central Bend Family Friendly,
1 2
cottage , Bend
This Bend, Oregon Mountain View cottage is conveniently located within 3 miles of St. Charles Bend, Saint Charles Hospital, and Pilot Butte State Park. The three-bathroom home features a fully equipped kitchen, washer/dryer, fireplace, balcony, free Wi-Fi, and parking; enjoy nearby hiking trails and the city's attractions.
Bend, OR
11/08 – 11/10
$434/nighttotal: $868 (2 )
Family-friendly Home W/ Fire Pit In Bend!
1 2
cottage , Bend
This pet-friendly Bend cottage, located in Mountain View, is less than 1.2 miles from St. Charles Bend and Pilot Butte State Park. The two-bathroom house features a fully equipped kitchen with microwave and dishwasher, free Wi-Fi, air conditioning, free parking, and a BBQ; guests can enjoy easy access to area hospitals and outdoor recreation.
10 1 review
Bend, OR
06/22 – 06/25
$351/nighttotal: $1053 (3 )
Oak Millhouse - Beautifully Restored Home In Downtown Old Bend
1 2
cottage , Bend
This mountain cabin in Bend's Old Bend district is a 7-minute walk to Drake Park and a 12-minute walk to the Old Mill District. This vacation rental offers a private terrace, fenced yard, barbecue, free Wi-Fi, fireplace, air conditioning, and a full kitchen, with nearby access to a laundromat and attractions like Deschutes Brewery.
9.8 326 reviews
Bend, OR
06/22 – 06/24
$328/nighttotal: $656 (2 )
Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/c, Walk Everywhere
2 4
cottage , Bend
This family-friendly cottage is located in Bend, just a short walk from the Old Mill District, Deschutes Historical Museum, and Hayden Homes Amphitheater. It has consistently received excellent ratings for cleanliness, location, and overall experience. The 700-square-foot cottage comfortably accommodates up to four guests in its two bedrooms and one bathroom. Amenities include a full kitchen, a private patio, a swimming pool, a spa, a fitness center, and high-speed internet access.
9.8 128 reviews
Bend, OR
11/08 – 11/10
$318/nighttotal: $636 (2 )
Cinder Cone - Salt Hot Tub, Gas Fireplace, 100+ Mbps Wifi, Bikes, Very Walkable!
2 2
cottage , Bend
This pet-friendly cottage in Bend's River West neighborhood is located one block from Galveston Avenue's shops and restaurants and five blocks from the Deschutes River and Mirror Pond, putting downtown Bend a short stroll away. This 850-square-foot rental accommodates up to six guests with two bedrooms, one bathroom, a full kitchen, a private saltwater hot tub, and complimentary cruiser bikes for exploring the area.
10 11 reviews
Bend, OR
10/22 – 10/26
$294/nighttotal: $1176 (4 )
Sweet Craftsman Bungalow In The Heart Of Bend
1 2
cottage , Bend
Sugar Plum Cottage is a cozy and charming cottage that accommodates up to four guests in one queen bed and a queen sleeper sofa. It’s located in Bend’s vibrant Westside, a short walk from Galveston's food carts, breweries, and the river wave at McKay Park. The cottage offers a fully equipped kitchen with modern appliances, a covered porch, and a spa, ensuring a comfortable and relaxing stay. It also provides free Wi-Fi, cable TV, and TDS TV+ streaming capabilities for entertainment.
9.2 22 reviews
Bend, OR
06/22 – 06/24
$460/nighttotal: $920 (2 )
Modern Cottage Charm & Walk To Downtown Bend
3 4
cottage , Bend
This Bend lakefront home is a 10-minute walk from Downtown Bend and the Deschutes River, with Drake Park and the Tower Theater a short 15-minute walk or drive away. This 1,080-square-foot vacation rental boasts four bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, a private swimming pool, a jacuzzi, a tennis court, and free Wi-Fi.
10 2 reviews
Bend, OR
10/22 – 10/26
$279/nighttotal: $1116 (4 )
North Sister - Bungalow Charm, Fireplace, Queen Bed, Parking
1 2
cottage , Bend
This 530 square foot cottage in Bend's Old Bend district is a 10-minute walk from the Old Mill District and a 4-minute drive from the Deschutes Historical Museum, offering proximity to mountain and lake views. This 2-bedroom, 1-bathroom dwelling accommodates up to 3 guests and features a full kitchen, air conditioning, free WiFi, a garden, and a patio with a barbecue, ideal for exploring nearby Hayden Homes Amphitheater and Bend Rock Gym.
9.7 683 reviews
Bend, OR
10/22 – 10/26
$133/nighttotal: $532 (4 )
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park
1 2
cottage , Bend
This centrally located cottage is within walking distance of Bend's top attractions, including Drake Park and the Deschutes River. With excellent user, location, and cleanliness ratings, this 420-square-foot cottage comfortably accommodates up to 2 guests in its 1 bedroom and 1 bathroom layout. Enjoy amenities such as a fully equipped kitchen, a private patio, a water park, a garden, barbecue grills, a TV, free on-site parking, and even a spa. Pets are also welcome for an additional fee.
Compare Family-Friendly Cottages in Bend, OR
Getting the cottage right makes all the difference for a successful family trip to Bend, OR.
9.7 278 reviews
Bend, OR
10/22 – 10/26
$296/nighttotal: $1184 (4 )
Historic Downtown Walk Everywhere Private Hot Tub One Block To River
2 2
cottage , Bend
The River Run cottage is located in Bend, just a short walk from the Deschutes River and the historic downtown area, making it a perfect base for exploring the city's attractions. The cottage has earned excellent ratings for its location, cleanliness, and overall guest experience. The cozy cottage offers 1890 square feet of space, accommodating up to four guests in its two bedrooms and two bathrooms. Enjoy modern amenities, a private hot tub, a fully fenced backyard, and seasonal extras like a BBQ and bikes, ensuring a comfortable and relaxing stay.
9.4 176 reviews
Bend, OR
11/08 – 11/10
$331/nighttotal: $662 (2 )
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries
2 2
cottage , Bend
This family-friendly cottage sits just a short walk from the Deschutes River, Old Mill District, and Hayden Homes Amphitheater, placing you close to Bend's best attractions and activities. It also has excellent user ratings, ensuring a comfortable and enjoyable stay. This two-bedroom cottage, spanning 950 square feet, comfortably accommodates up to six guests. Enjoy a private yard, swimming pool, spa, and fitness center, all while taking advantage of the fully equipped kitchen, air conditioning, and high-speed internet.
Bend, OR
08/01 – 08/31
$618/nighttotal: $18540 (30 )
Westside Vibes - Walkable W/ Salt Water Hot Tub Too!
3 2
cottage , Bend
This River West cottage in Bend offers prime downtown walkability, located just one block from Galveston Street and within walking distance of The Lot food cart pod and the Deschutes River. This 960 sq ft rental accommodates up to 6 guests with 3 bedrooms and 1 bathroom, featuring a private saltwater hot tub, a fully fenced yard, a propane BBQ, instruments for jam sessions, and central heat and air conditioning.
9.8 407 reviews
Bend, OR
06/24 – 06/28
$543/nighttotal: $2172 (4 )
Vintage Awbrey- Fireplace, Hot Tub, Ac, 100+mbps Wifi, Bikes, Walk Downtown
2 2
cottage , Bend
This vintage-modern apartment is situated in the heart of Bend's Old Mill District, just three blocks from downtown and a short walk from Galveston Avenue and Drake Park. It has excellent user, location, and cleanliness ratings. The apartment offers 1050 square feet of living space, with 2 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. It features a private hot tub, a spacious backyard with a grassy yard, patio with outdoor seating, and a gas BBQ grill. Guests have access to cruiser bikes, river floaties, and a ski waxing station, making it easy to enjoy Bend's outdoor activities.
Best Bend, OR cottages with a garden
9.8 344 reviews
Bend, OR
10/22 – 10/26
$290/nighttotal: $1160 (4 )
Historic Downtown Location Heart Of Bend Walk Everywhere Hot Tub High Demand
2 2
cottage , Bend
The Autumn Cottage is located on a quiet street just one block from Bend's historic downtown area, making it easy to walk to shops, restaurants, and the Deschutes River. The cottage consistently receives excellent ratings for location, cleanliness, and overall experience. This 850-square-foot home comfortably sleeps four guests in its two bedrooms and one bathroom. Enjoy modern amenities like air conditioning, a private hot tub, a fully fenced backyard with a grassy lawn, and a variety of extras like cruiser bikes and a propane BBQ.
10 5 reviews
Bend, OR
07/24 – 07/26
$708/nighttotal: $1416 (2 )
Fir Millhouse - Lovely Historic Cottage In Downtown Bend
1 2
cottage , Bend
This non-smoking cottage is located in Bend's Old Bend district, offering proximity to sledding slopes and ice skating rinks, with Drake Park just a 7-minute walk away and the Old Mill District commercial complex a 12-minute walk. This accommodation features a private terrace, fenced courtyard, BBQ area, and fireplace, alongside a well-equipped kitchen with a fridge, microwave, and oven, plus complimentary Wi-Fi and air conditioning.
9.8 236 reviews
Bend, OR
10/22 – 10/26
$279/nighttotal: $1116 (4 )
Westside Cottage Fenced Yards Hot Tub One Block To Galveston Guest Favorite
2 2
cottage , Bend
The Westside Cottage is located on Bend's trendy west side, just a short walk from Galveston Avenue, placing you within easy reach of restaurants, breweries, and shops. This cottage has received excellent ratings for location, cleanliness, and overall experience. The cottage offers 880 square feet of space with two bedrooms, two bathrooms, and a capacity for four guests. Enjoy modern amenities, a private fenced backyard with a hot tub, and seasonal extras like cruiser bikes and a propane BBQ.
9.9 215 reviews
Bend, OR
10/22 – 10/26
$272/nighttotal: $1088 (4 )
Trendy West Side Walk To Breweries & Food Carts Hot Tub Fenced Outdoor Space
2 2
cottage , Bend
This charming Bend cottage is located on the west side of town, just a short walk from popular breweries, restaurants, and the Deschutes River. It has received excellent ratings for location, cleanliness, and overall experience. The cottage is a cozy 900 square feet, comfortably sleeping up to four guests in its two bedrooms and one bathroom. Amenities include a fully equipped kitchen, a private hot tub, a fenced backyard, and bikes for exploring the area.
Frequently Asked Questions about cottages in Bend, OR
When is the best time to rent a cottage in Bend, OR?
Spring and fall are the best times to visit Bend, offering pleasant weather and fewer crowds. You'll enjoy vibrant fall foliage in the fall and blooming wildflowers in the spring. Summer can be busy, but the weather is perfect for outdoor activities. Winter brings snow and skiing opportunities.
Why consider renting a cottage in Bend, OR for your stay?
Cottages offer a cozy and comfortable alternative to hotels, providing a home-away-from-home experience. Many cottages have unique features like fireplaces, private patios, and hot tubs, perfect for relaxing after a day of exploring. They often come equipped with kitchens, allowing you to prepare your own meals.
What are the best cottages with a pool in Bend, OR?
Can you easily explore Bend, OR on foot or by bike?
Bend is a very walkable city, especially the Old Mill District and downtown areas. You'll find bike paths along the Deschutes River and throughout the city, making it easy to explore on two wheels. There are also bike rental shops available throughout Bend.
What are the best cottages with a jacuzzi in Bend, OR?
These Bend, OR cottages feature private hot tubs and jacuzzis, perfect for a cozy soak.
9.9 291 reviews
Bend, OR
10/22 – 10/26
$239/nighttotal: $956 (4 )
Contemporary Chic West Side Walk Everywhere Hot Tub One Block To River
1 2
cottage , Bend
The Nest is a cozy and modern Bend home located just one block from Columbia Park and the Deschutes River, offering excellent user, location, and cleanliness ratings. This one-bedroom, one-bathroom house with a loft-style layout and 650 square feet of floor space comfortably accommodates two guests. Amenities include a king-sized bed, a large bathroom with a walk-in shower, a private two-person hot tub on the front deck, an outdoor dining area, a fully equipped kitchen, a coffee bar, and a ductless AC/heating system for year-round comfort.
9.2 31 reviews
Bend, OR
10/22 – 10/26
$230/nighttotal: $920 (4 )
Riverfront Cottage - Steam Room & Pet Friendly!
1 2
cottage , Bend
This riverfront cottage in Bend's River West neighborhood is steps from the Deschutes River and Pioneer Park, offering a 10-15 minute walk to downtown. This 650 sq ft rental accommodates up to 3 guests with 1 bedroom and 1 bathroom, featuring a steam room shower, heated floors, a gas fireplace, a full kitchen with laundry, and access to a shared indoor heated pool and hot tub.
Check Out Cottages with Fireplaces in Bend, OR
Experience a classic ski evening in Bend, OR with a cozy fireplace, included at these cottages near the slopes.
9.6 41 reviews
Bend, OR
09/17 – 09/19
$351/nighttotal: $702 (2 )
Walk To Downtown And Amphitheater
1 2
cottage , Bend
This 600 sq ft, 1-bedroom, 1-bathroom cottage in Bend's River West neighborhood is located near a water park and within 1 mile of the Hayden Homes Amphitheater and Des Chutes Historical Museum. This pet-friendly lodging offers air conditioning, a full kitchen with a fridge and microwave, a garden, a spa, and parking, with guest capacity for 2 people and a check-out time of 11:00 AM.
Bend, OR
11/08 – 11/10
$553/nighttotal: $1106 (2 )
Bend Golf & Country Club Vacation Home
1 2
cottage , Bend
This Southeast Bend cottage is conveniently located 0.7 miles from Bend Factory Stores, within 3 miles of the Old Mill District and the Deschutes River, and offers easy access to Riverbend Dog Park and Bend Rock Gym. The smoke-free home features a fireplace, complete kitchen with microwave and dishwasher, outdoor patio, free Wi-Fi, and free self-parking; it is air-conditioned and has a garden.
Bend, OR
11/08 – 11/10
$318/nighttotal: $636 (2 )
Pet-friendly Bend Home ~ 2 Mi To Downtown
1 2
cottage , Bend
This cottage is located in the Southern Crossing neighborhood of Bend, within a 15-minute walk of the Old Mill District and the Deschutes River. The cottage has 2.5 bathrooms and a fully equipped kitchen with a microwave and dishwasher. The cottage also has a fireplace, a patio, and free Wi-Fi. Guests can enjoy the convenience of free self-parking and a smoke-free environment. The cottage is pet-friendly and has air conditioning.