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

69 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

69 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.

A Stone's Throw | Aspen House - Bend, OR
9.8 338 reviews

A Stone's Throw | Aspen House

apartment, 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.
One Block To Downtown, Hot Tub, Private Home, Yard - Bend, OR
9.7 285 reviews

One Block To Downtown, Hot Tub, Private Home, Yard

apartment, 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.
Cinder Cone - Salt Hot Tub, Gas Fireplace, 100+ Mbps Wifi, Bikes, Very Walkable! - Bend, OR
9.8 128 reviews

Cinder Cone - Salt Hot Tub, Gas Fireplace, 100+ Mbps Wifi, Bikes, Very Walkable!

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.

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.

Fir Millhouse - Lovely Historic Cottage In Downtown Bend - Bend, OR
9.6 7 reviews

Fir Millhouse - Lovely Historic Cottage In Downtown Bend

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.
North Sister - Bungalow Charm, Fireplace, Queen Bed, Parking - Bend, OR
10 2 reviews

North Sister - Bungalow Charm, Fireplace, Queen Bed, Parking

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.

Frequently Asked Questions about cottages in Bend, OR

Popular destinations

Best Bend, OR cottages with a garden

A Stone's Throw | Aspen House - Bend, OR
9.8 338 reviews

A Stone's Throw | Aspen House

apartment, 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.
Oak Millhouse - Beautifully Restored Home In Downtown Old Bend - Bend, OR
10 2 reviews

Oak Millhouse - Beautifully Restored Home In Downtown Old Bend

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.
Modern Historic Cottage In Core Downtown - Bend, OR
9.9 219 reviews

Modern Historic Cottage In Core Downtown

apartment, 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.
First Street Rapids And River Trail - Bend, OR
9.8 37 reviews

First Street Rapids And River Trail

cottage, Bend
This charming cottage is located on the west side of Bend, just a short walk from the river trail and a 10-minute stroll to the bustling downtown area. Guests consistently rate this property as excellent, praising its convenient location and cozy atmosphere. This two-bedroom, one-bathroom home spans 1100 square feet, comfortably accommodating up to six guests. Enjoy modern amenities including air conditioning, a fully equipped kitchen, and a private garden, perfect for relaxing after a day of exploring Bend's natural wonders and vibrant downtown.

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.

Cottage Along Deschutes River Trail W Epic Views - Bend, OR
9.8 115 reviews

Cottage Along Deschutes River Trail W Epic Views

cottage, Bend
This Bend studio rental offers riverfront access to the Deschutes River Trail and is a ten-minute walk from downtown Bend's restaurants and shops.
The private unit includes a kitchen with a fridge, freezer, and microwave, air conditioning, an indoor heated pool and hot tub, on-site laundry, and accommodates two guests.

Choose the Right Pet-Friendly Cottages in Bend, OR

Traveling with a pet to Bend, OR is easy with these cottages, offering a warm welcome for your four-legged guests.

One Block To Downtown, Hot Tub, Private Home, Yard - Bend, OR
9.7 285 reviews

One Block To Downtown, Hot Tub, Private Home, Yard

apartment, Bend
Historic Downtown, Private Hot Tub, High Demand - Bend, OR
9.8 345 reviews

Historic Downtown, Private Hot Tub, High Demand

apartment, Bend
Riverfront Cottage - Steam Room & Pet Friendly! - Bend, OR
9.2 35 reviews

Riverfront Cottage - Steam Room & Pet Friendly!

cottage, Bend
Guest Favorite! Prime West Side Location, Hot Tub - Bend, OR
9.8 244 reviews

Guest Favorite! Prime West Side Location, Hot Tub

apartment, Bend
©2026 cozycozy.com