This charming cottage is situated in Westside Bend, just a short walk from the Galveston food cart lot and within 2.4 kilometres of downtown Bend, the river wave at McKay Park, and the Amphitheatre. The area offers a lively atmosphere with a mix of shops, restaurants, and breweries. This one-bedroom cottage provides 69 square metres of living space and can comfortably accommodate up to four guests. The cottage features a fully equipped kitchen, a covered porch, a patio off the master bedroom, and an outdoor dining area with a propane BBQ, making it ideal for both relaxing and entertaining.
10 1 review
Bend, OR
22/06 – 24/06
$491/nighttotal: $982 (2 )
Oak Millhouse - Beautifully Restored Home In Downtown Old Bend
1 2
cottage , Bend
This mountain lodge in Bend's Old Bend district is 560 metres from Drake Park and 960 metres from the Old Mill District shopping centre. This cosy holiday home offers air conditioning, a fireplace, free Wi-Fi, a well-equipped kitchen with an oven and microwave, and a private terrace with a barbecue, ideal for exploring nearby attractions like Deschutes Brewery and engaging in wildlife viewing.
Bend, OR
01/08 – 31/08
$864/nighttotal: $25920 (30 )
Westside Vibes - Walkable W/ Salt Water Hot Tub Too!
3 2
cottage , Bend
This detached house is situated in Bend's River West district, a mere 160 metres from Galveston Street and a short walk to The Lot food cart pod and the Deschutes River. Offering 89 square metres of living space for up to six guests, this pet-friendly property features a kitchen, a private saltwater hot tub, a garden with hammocks and seating, and off-street parking for three vehicles.
Bend, OR
08/11 – 10/11
$774/nighttotal: $1548 (2 )
Bend Golf & Country Club Vacation Home
1 2
cottage , Bend
This Southeast Bend cottage, situated 1.1 kilometres from Bend Factory Stores, offers easy access to the Old Mill District and Deschutes River, both within a 4.8 kilometre radius. The self-catering property includes a microwave, dishwasher, patio, fireplace, free Wi-Fi in public areas, and free on-site parking; nearby attractions include shopping at Bend Factory Stores and recreational opportunities along the Deschutes River.
Bend, OR
08/11 – 10/11
$3769/nighttotal: $7538 (2 )
Sleeps 40! 8 Modern Units/20 Bdrs W/ Deck+hot Tub, 10mins To Downtown & Old Bend
1 2
cottage , Bend
This Summit West cottage in Bend, Oregon is conveniently located within 1.6km of Discovery Park Off-Leash Area and Central Oregon Community College, and within 3.2km of Westside Church and Overturf Butte Off-Leash Area. This pet-friendly self-catering holiday home boasts a fully equipped kitchen, laundry facilities, a balcony, free Wi-Fi, and parking; the unusual number of twelve bathrooms requires further clarification.
Bend, OR
08/11 – 10/11
$607/nighttotal: $1214 (2 )
Family-friendly Home W/ Fire Pit In Bend!
1 2
cottage , Bend
This pet-friendly holiday home in Mountain View, Bend, Oregon is located within 2km of St Charles Bend and within 3km of Pilot Butte State Park. The self-catering property boasts two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi in communal areas, free parking, and barbecue facilities, making it ideal for exploring Bend and its surrounding attractions.
Bend, OR
08/11 – 10/11
$525/nighttotal: $1050 (2 )
Old Mill Getaway By Avantstay Private Backyard W/ Hot Tub
1 2
cottage , Bend
This Larkspur cottage in Bend, Oregon is situated less than 2km from Bend Rock Gym, Ponderosa Park Dog Park, and the Old Mill District, and under 3km from the Deschutes River and Bend Factory Stores. The self-catering property features a fully equipped kitchen, 2.5 bathrooms, a washer/dryer, private balcony, and television; pets are welcome.
10 2 reviews
Bend, OR
22/06 – 24/06
$534/nighttotal: $1068 (2 )
North Sister - Bungalow Charm, Fireplace, Queen Bed, Parking
1 2
cottage , Bend
This detached house is situated in Bend's Old Bend district, nestled by a lake, offering a 4-minute drive to the Deschutes Historical Museum and a 10-minute walk to the Old Mill District. This 49 square metre holiday home accommodates up to three guests across two bedrooms and one bathroom, featuring a well-equipped kitchen with a fridge and microwave, air conditioning, and a garden with barbecue facilities, ideal for exploring nearby outdoor recreation.
10 5 reviews
Bend, OR
20/06 – 27/06
$506/nighttotal: $3542 (7 )
Fir Millhouse - Lovely Historic Cottage In Downtown Bend
1 2
cottage , Bend
This non-smoking cottage is located in Bend's Old Bend district, a short walk from sledding hills and ice skating, with the Old Mill District 1.92 kilometres away and Drake Park 1.12 kilometres on foot. This holiday home offers complimentary Wi-Fi, a well-equipped kitchen, and a private terrace, with proximity to Pilot Butte State Park and Tumalo State Park for outdoor activities.
Bend, OR
08/11 – 10/11
$994/nighttotal: $1988 (2 )
2 Units Deck, Hot Tub, Minutes To Old Bend 1212 Skyline Ranch By Avantstay
1 2
cottage , Bend
This detached house in Summit West, Bend, is located less than 1.6 kilometres from Discovery Park Off-Leash Area and Central Oregon Community College, and within 3.2 kilometres of Westside Church and Overturf Butte Off-Leash Area. This pet-friendly cottage offers complimentary WiFi, air conditioning, a full kitchen with a dishwasher and fridge, a private balcony, and an in-unit washer/dryer, with free self-parking available.
9.8 236 reviews
Bend, OR
22/10 – 26/10
$389/nighttotal: $1556 (4 )
Westside Cottage Fenced Yards Hot Tub One Block To Galveston Guest Favorite
2 2
cottage , Bend
The Westside Cottage is situated on the trendy west side of Bend, just a short walk from the Deschutes River and the historic downtown area, offering easy access to the city's attractions and amenities. This cottage has received excellent reviews for its location, cleanliness and overall experience. The cottage is a comfortable and well-equipped two-bedroom home with two bathrooms, spanning 82 square metres and accommodating up to four guests. This charming property offers a private outdoor space with a patio, pergola, hot tub and barbecue, as well as amenities such as a fully equipped kitchen, free Wi-Fi, a washing machine and dryer, and two bicycles for exploring the area.
Bend, OR
08/11 – 10/11
$933/nighttotal: $1866 (2 )
1115 Aerie Buyout 2 Units, Near Downtown Hot Tub + Mountain View
1 2
cottage , Bend
This Summit West holiday home in Bend, Oregon is situated less than 2km from Discovery Park Off-Leash Area and Central Oregon Community College, and within 3km of Overturf Butte Off-Leash Area and Westside Church. This pet-friendly three-bathroom dwelling boasts a fully equipped kitchen, in-unit laundry, private balcony, free Wi-Fi, and free on-site parking, perfect for families or groups exploring Bend's outdoor attractions.
Best family friendly Bend, OR cottage rentals
Among the 76 accommodations in Bend, OR, here are the 4 best family friendly cottage rentals
9.8 128 reviews
Bend, OR
22/10 – 26/10
$501/nighttotal: $2004 (4 )
Cinder Cone - Salt Hot Tub, Gas Fireplace, 100+ Mbps Wifi, Bikes, Very Walkable!
2 2
cottage , Bend
This newly renovated cottage is situated on Bend's west side, just 100 metres from Galveston Avenue's shops and restaurants, 500 metres from the Deschutes River and Mirror Pond, and a short walk to downtown. This 79 square metre dwelling accommodates up to six guests with two bedrooms and one bathroom, offering a private saltwater hot tub, cruiser bikes for exploring, and a fully equipped eat-in kitchen with an outdoor patio and gas BBQ.
9.8 326 reviews
Bend, OR
22/06 – 24/06
$445/nighttotal: $890 (2 )
Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/c, Walk Everywhere
2 2
cottage , Bend
This family-friendly cottage is located in Bend, just a short walk from the Old Mill District and Hayden Homes Amphitheater, offering easy access to the city's main attractions. The cottage has consistently received excellent ratings for its location, cleanliness, and overall experience. The two-bedroom cottage spans 65 square metres and can comfortably accommodate up to four guests. It features a fully equipped kitchen, a private patio, and access to a swimming pool, a spa, a fitness centre, and a garden, making it the perfect base for exploring Bend and enjoying its natural beauty.
9.4 176 reviews
Bend, OR
22/10 – 26/10
$434/nighttotal: $1736 (4 )
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries
2 2
cottage , Bend
This charming cottage is situated in Bend, just a short walk from the Deschutes River, Old Mill District, and Hayden Homes Amphitheater, making it an ideal base for exploring the city's attractions. It has consistently received excellent reviews from previous guests. The cottage is a comfortable 88 square metres and can accommodate up to six people. It offers a range of amenities and features including a fully equipped kitchen, a private garden with barbecue facilities, and access to a water park.
9.2 22 reviews
Bend, OR
22/06 – 24/06
$671/nighttotal: $1342 (2 )
Modern Cottage Charm & Walk To Downtown Bend
3 2
cottage , Bend
This Bend lakefront holiday home, a 10-minute walk (1.6km) from the Deschutes River and Bend city centre, is also within a 15-minute walk (2.4km) of Drake Park and the Tower Theatre. The 100 square metre property sleeps six in four bedrooms and one bathroom, boasting a fully equipped kitchen, swimming pool, jacuzzi, tennis court, and free Wi-Fi; housekeeping is available on request.
Best Bend, OR cottages with a garden
9.7 683 reviews
Bend, OR
19/06 – 20/06
$355/nightfor 1 night
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park
1 2
cottage , Bend
This charming cottage is located in the heart of Bend, just a kilometre from Drake Park and the Deschutes River, offering easy access to the city's vibrant downtown area. The property consistently receives excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers. The cottage offers a comfortable and convenient space for two guests, with a floor area of 39 square metres, one bedroom, and one bathroom. Enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, a swimming pool, and a terrace, perfect for relaxing after a day of exploring Bend's attractions.
9.8 407 reviews
Bend, OR
06/07 – 11/07
$777/nighttotal: $3885 (5 )
Vintage Awbrey- Fireplace, Hot Tub, Ac, 100+mbps Wifi, Bikes, Walk Downtown
2 2
cottage , Bend
This charming, vintage-modern home is located in the Westside neighbourhood of Bend, just a short walk from the downtown area and close to the Newport district. It has received excellent ratings for location, cleanliness, and overall user experience. The two-bedroom apartment spans 98 square metres and comfortably accommodates up to six guests. The property offers a range of amenities, including a private garden with a hot tub, a fully equipped kitchen, and a fitness centre, making it perfect for a relaxing and enjoyable stay in Bend.
9.6 41 reviews
Bend, OR
17/09 – 19/09
$504/nighttotal: $1008 (2 )
Walk To Downtown And Amphitheater
1 2
cottage , Bend
This charming cottage is located in River West, Bend, offering convenient access to the Hayden Homes Amphitheater and the Des Chutes Historical Museum, with a water park nearby. This 56 square meter dwelling accommodates two guests and features a well-equipped kitchen with a fridge and microwave, air conditioning, a garden, a spa, and parking, with the added benefit of internet access and allowing pets.
Bend, OR
08/11 – 10/11
$444/nighttotal: $888 (2 )
Pet-friendly Bend Home ~ 2 Mi To Downtown
1 2
cottage , Bend
This charming cottage is located in the Southern Crossing district of Bend, just a short distance from popular attractions like the Old Mill District and Hayden Homes Amphitheater. The cottage is situated within easy reach of the Deschutes River and Bend Factory Stores, providing convenient access to the area's best offerings. The cottage offers comfortable accommodation with 2.5 bathrooms, providing ample space for families or groups of friends. The property features a fully equipped kitchen, a fireplace, a patio, and a barbecue, allowing guests to enjoy a relaxing and comfortable stay.
Frequently Asked Questions about cottages in Bend, OR
What would be a good 2-days itinerary for visiting Bend, OR?
On your first day, head to the Old Mill District for some shopping and grab lunch at Anthony's at the Old Mill. In the afternoon, explore the Deschutes River Trail and enjoy the scenery. In the evening, catch a show at the Tower Theatre. On your second day, drive up to the top of Pilot Butte State Scenic Viewpoint for panoramic views of Bend and the surrounding area. Then, visit the High Desert Museum to learn about the history and culture of the region. In the evening, enjoy a delicious meal at one of the many fantastic restaurants in Bend.
What part of Bend, OR is ideal for renting a cottage?
The best area for renting a cottage in Bend is the west side of town, close to the Deschutes River. You'll find many charming cottages in the areas of River Pines, Westside, and the Old Mill District, all within easy reach of the river, parks, and trails.
What are the best cottage rentals with a pool in Bend, OR?
When is the best time to rent a cottage in Bend, OR?
The best time to rent a cottage in Bend is during the shoulder seasons, from April to May and September to October. The weather is still pleasant during these months, but the crowds are smaller and the prices are lower.
What are the best cottage rentals with a jacuzzi in Bend, OR?
You can't miss the Old Mill District, with its historic mill and shops, the Deschutes River Trail for stunning river views, and the Pilot Butte State Scenic Viewpoint for breathtaking panoramic views of Bend and the surrounding area.
What are the best cottage rentals for families and kids in Bend, OR?
Why consider renting a cottage in Bend, OR for your stay?
Renting a cottage in Bend offers a more intimate and homey experience than a hotel. You'll have your own space to relax and unwind, and many cottages come with amenities like kitchens and fireplaces, perfect for a cosy getaway.
What are the best pet friendly cottage rentals in Bend, OR?
Can you easily explore Bend, OR on foot or by bike?
Bend is a very walkable and bike-friendly city. You can easily explore the downtown area, the Old Mill District, and the Deschutes River Trail on foot or by bike. There are also many bike paths and trails around the city, making it a great place to explore on two wheels.
What are the best cottage rentals with parking in Bend, OR?
What are the best restaurants in Bend, OR with nature views?
For stunning views, try the upscale dining at The Pine Tavern, offering a beautiful forest setting, or the casual atmosphere of The Riverhouse, with its riverside patio and views of the Deschutes River.
What family-friendly activities are available in Bend, OR?
Bend is a fantastic destination for families. There are plenty of family-friendly activities, including the High Desert Museum, the Discovery Center, the Pilot Butte State Scenic Viewpoint, and the many parks and playgrounds around the city. For a fun adventure, take a ride on the Oregon High Desert Trail or visit the Sunriver Nature Center & Observatory.
Destinations nearby
Best Bend, OR cottage rentals with jacuzzi
Among the 76 accommodations in Bend, OR, here are the 4 best cottage rentals with a jacuzzi
9.2 31 reviews
Bend, OR
08/11 – 10/11
$298/nighttotal: $596 (2 )
Riverfront Cottage - Steam Room & Pet Friendly!
1 2
cottage , Bend
This riverside lodge in Bend's River West district offers direct access to the Deschutes River and its trail, with downtown Bend a 10 to 15-minute walk away and Pioneer Park adjacent. This 60 square meter holiday home, accommodating up to three guests, features one bedroom, one bathroom with a steam shower, a fully equipped kitchen, air conditioning, a private patio, and access to a shared indoor heated pool and hot tub.
9.7 278 reviews
Bend, OR
22/10 – 26/10
$414/nighttotal: $1656 (4 )
Historic Downtown Walk Everywhere Private Hot Tub One Block To River
2 2
cottage , Bend
The River Run cottage is situated in a central Bend neighbourhood, just a short walk from the Deschutes River and the historic downtown area, offering easy access to restaurants, shops, and galleries. This charming property enjoys excellent user, location, and cleanliness ratings. The cottage spans 176 square metres and comfortably accommodates four guests in two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen with Viking appliances, a private hot tub, a fenced backyard with a deck, and access to two cruiser bikes during the summer months.
9.9 215 reviews
Bend, OR
22/10 – 26/10
$381/nighttotal: $1524 (4 )
Trendy West Side Walk To Breweries & Food Carts Hot Tub Fenced Outdoor Space
2 2
cottage , Bend
The Sunrise Cottage is situated on Bend’s popular west side, just a short walk from 10 Barrel Brewing Company, Ariana’s, and the historic downtown area. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The two-bedroom cottage spans 84 square metres and comfortably accommodates up to four guests. It offers a range of modern amenities, including a fully equipped kitchen, air conditioning, high-speed internet, a private hot tub, and a fenced backyard with a deck and gazebo, perfect for enjoying the beautiful Bend weather.
9.9 291 reviews
Bend, OR
22/10 – 26/10
$334/nighttotal: $1336 (4 )
Contemporary Chic West Side Walk Everywhere Hot Tub One Block To River
1 2
cottage , Bend
The Nest is a self-contained house situated just 0.8km from Columbia Park and the Deschutes River in Bend, Oregon, offering a peaceful escape close to nature. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The house spans 60 square metres and comfortably accommodates two guests in a single bedroom and bathroom. The Nest offers a range of amenities for a relaxing stay, including a private hot tub, a fully equipped kitchen, a terrace, and access to two cruiser bikes for exploring the area.
Best Bend, OR cottages with a fireplace
Bend, OR
08/11 – 10/11
$515/nighttotal: $1030 (2 )
Ponderosa Pines By Avantstay Gorgeous Deck, 10 Mins From Central Bend Family Friendly,
1 2
cottage , Bend
This Bend Mountain View holiday home is conveniently located within 5km of Saint Charles Bend hospital and Pilot Butte State Scenic Viewpoint. The three-bathroom property offers a fully equipped kitchen, fireplace, washer/dryer, balcony, free Wi-Fi, and parking, plus proximity to Big Sky Off-Leash Dog Park.