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.

Westside Vibes - Walkable W/ Salt Water Hot Tub Too! - Bend, OR
No reviews

Westside Vibes - Walkable W/ Salt Water Hot Tub Too!

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.
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.
Modern Cottage Charm & Walk To Downtown Bend - Bend, OR
9.2 22 reviews

Modern Cottage Charm & Walk To Downtown Bend

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.
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries - Bend, OR
9.6 178 reviews

Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries

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.

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.

A Stone's Throw | Vintage Awbrey - Bend, OR
9.8 413 reviews

A Stone's Throw | Vintage Awbrey

apartment, 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.
Oak Millhouse - Beautifully Restored Home In Downtown Old Bend - Bend, OR
10 1 review

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.

Frequently Asked Questions about cottages in Bend, OR

Popular destinations

Best Bend, OR cottages with a garden

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.
Oak Millhouse - Beautifully Restored Home In Downtown Old Bend - Bend, OR
10 1 review

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.
Fir Millhouse - Lovely Historic Cottage In Downtown Bend - Bend, OR
9.8 6 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.
Walk Everywhere, Private Hot Tub, Modern Chic - Bend, OR
9.9 291 reviews

Walk Everywhere, Private Hot Tub, Modern Chic

bungalow, 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.

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.

A Stone's Throw | Vintage Awbrey - Bend, OR
9.8 413 reviews

A Stone's Throw | Vintage Awbrey

apartment, 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.
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.
Westside Vibes - Walkable W/ Salt Water Hot Tub Too! - Bend, OR
No reviews

Westside Vibes - Walkable W/ Salt Water Hot Tub Too!

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.
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.

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.

Walk Everywhere, Private Hot Tub, Modern Chic - Bend, OR
9.9 291 reviews

Walk Everywhere, Private Hot Tub, Modern Chic

bungalow, Bend
Walk To Downtown And Amphitheater - Bend, OR
9.6 41 reviews

Walk To Downtown And Amphitheater

cottage, Bend
Beaumont - Easy Access To All Of Central Oregon - Bend, OR
No reviews

Beaumont - Easy Access To All Of Central Oregon

cottage, Bend
Modern Cottage Charm & Walk To Downtown Bend - Bend, OR
9.2 22 reviews

Modern Cottage Charm & Walk To Downtown Bend

cottage, Bend
©2026 cozycozy.com