Search cheap cottages in Bend, OR from 100+ sites!

76 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Bend, OR cottages
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

76 Best cottages in Bend, OR

Compare Family-Friendly Cottages in Bend, OR

Getting the cottage right makes all the difference for a successful family trip to Bend, OR.

Historic Downtown Walk Everywhere Private Hot Tub One Block To River - 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.
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries - Bend, OR
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.
Westside Vibes - Walkable W/ Salt Water Hot Tub Too! - Bend, OR
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.
Vintage Awbrey- Fireplace, Hot Tub, Ac, 100+mbps Wifi, Bikes, Walk Downtown - Bend, OR
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

Historic Downtown Location Heart Of Bend Walk Everywhere Hot Tub High Demand - Bend, OR
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.
Fir Millhouse - Lovely Historic Cottage In Downtown Bend - Bend, OR
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.
Westside Cottage Fenced Yards Hot Tub One Block To Galveston Guest Favorite - Bend, OR
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.
Trendy West Side Walk To Breweries & Food Carts Hot Tub Fenced Outdoor Space - Bend, OR
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

Destinations nearby

Find the Best Cottages with a Hot Tub in Bend, OR

These Bend, OR cottages feature private hot tubs and jacuzzis, perfect for a cozy soak.

Contemporary Chic West Side Walk Everywhere Hot Tub One Block To River - Bend, OR
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.
Riverfront Cottage - Steam Room & Pet Friendly! - Bend, OR
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.

Walk To Downtown And Amphitheater - Bend, OR
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 Golf & Country Club Vacation Home - Bend, OR
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.
Pet-friendly Bend Home ~ 2 Mi To Downtown - Bend, OR
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.
©2026 cozycozy.com