What should a first-time visitor not miss in Bend, OR?

You definitely want to check out the Old Mill District, it's a great place to wander around, grab a bite to eat and enjoy the views of the Deschutes River. You can't go wrong with a trip to the top of Pilot Butte for panoramic views of Bend and the surrounding area. And, of course, you'll want to explore the Cascade Lakes Highway, it's a scenic route that takes you past some of the most beautiful lakes in the area.

What are the best Airbnb and vacation rentals in Bend, OR?

Private Apartment - Your Bend Escape - Right In Town , Kathy's Westside Perch and The Garden Apt-hot Tub Fireplace Ac 250+ Mbps are the most popular Airbnb and vacation rentals in Bend, OR among travelers.

Which neighborhood in Bend, OR should you consider for a vacation rental?

The Old Mill District is a popular choice for vacation rentals, as it's close to the river and has lots of restaurants and shops. If you're looking for a quieter neighbourhood, consider staying in the Westside, which is known for its family-friendly atmosphere. For a more central location, the downtown area is a great choice.

What are the most popular Airbnbs in Bend, OR?

Among the Airbnbs in Bend, OR, Private Apartment - Your Bend Escape - Right In Town , Kathy's Westside Perch and The Garden Apt-hot Tub Fireplace Ac 250+ Mbps are the most popular ones.

What are the top family-friendly attractions in Bend, OR?

The High Desert Museum is a great place to learn about the local wildlife and culture, and the Pilot Butte State Scenic Viewpoint offers fantastic views of the city and surrounding area. And don't forget the Drake Park, it's a great place for a picnic and a stroll.

What are the best vacation rentals with a pool in Bend, OR?

Historic Belle Millhouse In Bend - Or - Walk To Downtown -vrbo , Beautiful Home Overlooking The River-minutes To It All and Bernhard Justice- Salt Hot Tub - 100+ Wifi - Gas Firepl - Bikes - Ev Plug - Walkable are the best vacation rentals with a pool in Bend, OR.

When is the best time to book a vacation rental in Bend, OR?

The best time to book is during the shoulder season, from April to May or September to October. You'll avoid the summer crowds and the prices are usually lower.

What are the best rentals for families and kids in Bend, OR?

The best rentals for families and kids in Bend, OR are Cozy Bookworm's Retreat In Bend , Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub and Historic Belle Millhouse In Bend - Or - Walk To Downtown -vrbo .

What are the best budget-friendly activities in Bend, OR?

The Deschutes River is perfect for a free day of swimming, sunbathing, or kayaking. You can also walk or cycle the Deschutes River Trail, which stretches for 23 km along the river. And there are plenty of free concerts and events happening in the city throughout the year.

What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?

The best vacation rentals or Airbnb with a jacuzzi in Bend, OR are The Garden Apt-hot Tub Fireplace Ac 250+ Mbps , Tranquil & Magical-hottub Fireplace Ac 250 Mbps+ and Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub .

What are the best restaurants with local dishes in Bend, OR?

Try the Anthony's at the Old Mill, they have a great selection of fresh seafood and local dishes. There's also The Pine Tavern, it's a classic Bend restaurant with a menu full of local favourites.

What are the best walking or cycling routes in Bend, OR?

The Deschutes River Trail is a great option for both walking and cycling, you can also check out the Tumalo Creek Trail, it's a beautiful trail that winds through the forest.

Are there pet-friendly attractions in Bend, OR?

Yes, many of the parks and trails in Bend are pet-friendly, including the Drake Park and the Deschutes River Trail. There are also a number of restaurants and shops that welcome dogs.

What are the benefits of choosing a vacation rental in Bend, OR?

Vacation rentals offer more space and privacy than a hotel, and they often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.

What are the top sports attractions and facilities in Bend, OR?

Bend is a great place for outdoor sports, with plenty of opportunities for hiking, biking, skiing, and snowboarding. The Mount Bachelor Ski Resort is a popular destination for winter sports, and there are also several golf courses in the area.

Best Vacation Rentals & Airbnb in Bend, OR for 2026

No reviews

River Ridge 420ab - Condo W/views, Pool & Hot Tub

house, Bend

River Ridge Condo 420 is a three-bedroom, three-bathroom condominium situated within the Mount Bachelor Village Resort in Bend, Oregon, offering panoramic views of the Deschutes River.
This property accommodates up to six guests and features air conditioning, a kitchen with a fridge, freezer, microwave, and dishwasher, a swimming pool, Jacuzzi, garden, and parking, with proximity to outdoor recreation opportunities.

9.9 336 reviews

Westside Bungalow - Heart Of Bend

apartment, Bend

This Westside Bend cottage is conveniently located within walking distance of the Deschutes River and numerous breweries and restaurants.
The two-bedroom, two-bathroom property sleeps four guests and features a fully equipped kitchen, in-unit laundry, a large fenced yard, and ample off-street parking.

No reviews

Bluebird Day - Pine Hideaway

house, Bend

Bluebird Day - Pine Hideaway is a pet-friendly house in Bend, Oregon, located 1.9 kilometres from Drake Park and within a 6.6-kilometre radius of Hollinshead and Ponderosa Parks.
This one-bedroom property sleeps five, boasts a fully equipped kitchen with fridge, microwave, and dishwasher, plus free Wi-Fi, parking, and air conditioning; guests under 25 require a parent or guardian to check in.

9.9 65 reviews

Private Pine Retreat | Hot Tub | Relax & Reset

apartment, Bend

This two-bedroom apartment is situated in Bend, just a short distance from Central Oregon Community College and Westside Church, and within easy reach of Drake Park and Tower Theater. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment spans 167 square metres and comfortably accommodates up to four guests. It boasts a fully equipped kitchen, a spacious living area, and a private garden, perfect for relaxing after a day of exploring Bend's attractions.

9.2 23 reviews

New! Affordable Mountain Escape | Pool - Hot Tub | Near Mt. Bachelor

apartment, Bend

This flat in Bend's Century West district is just steps from the Deschutes River Trail and within walking distance of the Hayden Homes Amphitheater and Drake Park, with downtown Bend and the Old Mill District a 5-minute drive away, and Mt. Bachelor Ski Resort 25 kilometres distant.
This 57 square metre apartment offers two bedrooms, one bathroom, and accommodation for three guests, featuring a fully equipped kitchen with a fridge, microwave oven, and dishwasher, plus a communal swimming pool, jacuzzi, terrace, and parking.

9.8 16 reviews

Bend Basecamp! Condo W/ Pool Near Deschutes River

apartment, Bend

This Mount Bachelor Village condo is conveniently located a short drive from Bend city centre and Mount Bachelor ski resort.
The single-storey apartment sleeps four, featuring a king bed, queen sleeper sofa, fully equipped kitchen, washer/dryer, two Smart TVs, an electric fireplace, covered balcony with gas grill, and access to a seasonal outdoor pool, hot tub, and communal gardens.

9.9 155 reviews

Spacious Two Story 2 Bed 2 Bath West Side Condo

house, Bend

This family-friendly apartment is located in Bend's Century West district, just 3 kilometres from the Deschutes River, Old Mill District, and Hayden Homes Amphitheater. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious, with 132 square metres of floor area and room for up to 6 guests. It boasts a fully equipped kitchen, a fireplace, a terrace, a swimming pool, a jacuzzi, and a garden, perfect for relaxing after a day of exploring Bend.

9.8 6 reviews

New Charming Home Located In Downtown Bend!

apartment, Bend

This two-bedroom flat is located in central Bend, within 500 meters of the Tower Theatre, Des Chutes Historical Museum, Deschutes Brewery, and Regal Old Mill, offering convenient pedestrian access to local amenities and the Des Chutes River.
This family-friendly apartment sleeps up to six guests and features air conditioning, Wi-Fi, a full kitchen, a private terrace, and parking, with a luxurious bathroom including a heated pebble floor and a rain shower.

10 19 reviews

Close To River And Trails - New Ev Charger!

apartment, Bend

This Westside Bend guesthouse, a 10-minute walk from the Deschutes River and a short drive from Bend city centre, the Old Mill District, and Mount Bachelor ski resort, offers a 37% monthly discount resulting in a nightly rate of £76.50 (approx. $94.50 USD).
The property comprises two bedrooms, a cosy loft, one bathroom, a private deck, and on-site laundry facilities, comfortably accommodating up to four guests and featuring a fully equipped kitchen, Jacuzzi, and air conditioning.

9.9 84 reviews

King Bed| Clean | Fast Wi-fi | Firepit | Peaceful

apartment, Bend

This apartment is situated in a peaceful neighbourhood in Bend, just 6.4 kilometres from Downtown Bend, 8 kilometres from Pilot Butte, and 8 kilometres from the Deschutes Brewery. The property has consistently received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This three-bedroom, two-bathroom home can accommodate up to six guests. It offers a fully equipped kitchen, a dedicated workspace with high-speed internet, a private garden with a gazebo and patio seating, and a jacuzzi.

No reviews

20 Min To Mt Bachelor Perfect Basecamp For Skiers

apartment, Bend

This Bend apartment offers a convenient base near Ponderosa and Hollinshead Parks, approximately 8 kilometres from each, and a short drive from Drake Park, providing easy access to green spaces and outdoor activities.
The 65 square metre self-catering flat sleeps three, features a kitchenette with microwave and fridge, free Wi-Fi, parking, and air conditioning, and is ideally located for exploring Bend and Mount Bachelor (a 32 km drive).

No reviews

Spacious Kitchen And Elegant Interiors - Amazing Forest Retreat

house, Bend

This detached house is situated in Bend's west side, offering convenient access to the town centre's shops and restaurants, located approximately 1.6 kilometres away.
This spacious, two-level property accommodates up to 10 guests across four bedrooms, featuring air conditioning, free WiFi, a fully equipped kitchen, and an upstairs family room with games.

Best family friendly Bend, OR vacation rentals

Among the 3745 accommodations in Bend, OR, here are the 4 best family friendly rentals

No reviews

Fully Furnished 30+ Day Executive Rental Utilities Included

apartment, Bend

This two-bedroom flat in Bend's Old Mill District is a short walk from the Deschutes River, Hayden Homes Amphitheater, and numerous shops and eateries.
Spanning 92 square meters, this pet-friendly accommodation accommodates up to four guests and features a garden, spa, parking, and a dedicated workspace with high-speed internet.

9.8 62 reviews

One Level 7mins To Oldmills District Petsok 5 Beds

apartment, Bend

This spacious three-bedroom apartment is situated in the Foxborough neighbourhood of Southeast Bend, just 7km from the Old Mill District and 9km from the Deschutes River Trail and Farewell Park. It has consistently received excellent reviews for its location, cleanliness, and overall user experience.
The 132 square metre apartment comfortably accommodates up to 8 guests and features a large open-plan living area, a well-equipped kitchen, and a fenced-in backyard. Amenities include a jacuzzi, a fireplace, a BBQ, a smart TV with Netflix and YouTube TV, and a washer and dryer.

9.9 467 reviews

The Heart Of Bend. Brownstone Apartment.

apartment, Bend

This studio apartment is located in the Old Mill District, a short walk from the Deschutes River and a 5-minute walk from the Bend Amphitheater, offering easy access to the area's attractions and amenities. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The self-catering property spans 81 square metres, comfortably accommodating up to 3 guests in a single bedroom and bathroom. The studio is equipped with a kitchen, air conditioning, a terrace, a garden, and parking, providing everything you need for a comfortable stay.

9.2 22 reviews

Modern Cottage Charm & Walk To Downtown Bend

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 vacation rentals with a fireplace

No reviews

Charming Flat With Outdoor Fire Pit And Scenic Views - Delightful Retreat

apartment, Bend

This newly renovated 65-square-meter flat is situated on the downtown end of the Galveston corridor in Bend, just 100 meters from the Galveston Bridge overlooking the river and directly across from Drake Park.
The apartment sleeps four and offers two bedrooms, a fully equipped kitchen, air conditioning, and outdoor seating with park views, providing convenient access to shops, eateries, and Deschutes River activities.

10 24 reviews

Cozy & Luxurious Guest House In The Heart Of Bend!

house, Bend

This Bend apartment, a 600 sq ft (56 sq m) custom-built property above a garage, is a 1.6km walk from Bend's downtown area, offering easy access to restaurants and a grocery store.
The open-plan loft features a king and queen bed, sleeping four guests (though only children can stand upright in the loft), and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and a garden.

9.5 704 reviews

The Mallard House Walk To Downtown Bend In 5 Mins

apartment, Bend

The Mallard house is situated on the west side of Bend, just a 1.6km walk from the town centre through Drake Park, and within easy reach of shops and restaurants. This apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, one-bathroom property comfortably sleeps four guests, with a fenced yard perfect for pets. The Mallard house includes a fully equipped kitchen, air conditioning, parking, and an EV charger, as well as a charming herb garden for guests to enjoy.

9.6 178 reviews

Ground Floor Ski/river Condo #152

apartment, Bend

This cosy apartment is situated in the Mt. Bachelor Village area, just minutes from the ski resort and forest trails, and steps from the Deschutes River trail. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment can accommodate up to four guests and features a fireplace, a sofa bed, and a washer and dryer. Guests can enjoy the peaceful surroundings on the private deck, relax by the swimming pool, or explore the park-like setting with wildlife viewing opportunities.

Frequently Asked Questions about vacation rentals in Bend, OR

What should a first-time visitor not miss in Bend, OR?
You definitely want to check out the Old Mill District, it's a great place to wander around, grab a bite to eat and enjoy the views of the Deschutes River. You can't go wrong with a trip to the top of Pilot Butte for panoramic views of Bend and the surrounding area. And, of course, you'll want to explore the Cascade Lakes Highway, it's a scenic route that takes you past some of the most beautiful lakes in the area.
What are the best Airbnb and vacation rentals in Bend, OR?
Private Apartment - Your Bend Escape - Right In Town, Kathy's Westside Perch and The Garden Apt-hot Tub Fireplace Ac 250+ Mbps are the most popular Airbnb and vacation rentals in Bend, OR among travelers.
Which neighborhood in Bend, OR should you consider for a vacation rental?
The Old Mill District is a popular choice for vacation rentals, as it's close to the river and has lots of restaurants and shops. If you're looking for a quieter neighbourhood, consider staying in the Westside, which is known for its family-friendly atmosphere. For a more central location, the downtown area is a great choice.
What are the most popular Airbnbs in Bend, OR?
Among the Airbnbs in Bend, OR, Private Apartment - Your Bend Escape - Right In Town, Kathy's Westside Perch and The Garden Apt-hot Tub Fireplace Ac 250+ Mbps are the most popular ones.
What are the top family-friendly attractions in Bend, OR?
The High Desert Museum is a great place to learn about the local wildlife and culture, and the Pilot Butte State Scenic Viewpoint offers fantastic views of the city and surrounding area. And don't forget the Drake Park, it's a great place for a picnic and a stroll.
What are the best vacation rentals with a pool in Bend, OR?
Historic Belle Millhouse In Bend - Or - Walk To Downtown -vrbo, Beautiful Home Overlooking The River-minutes To It All and Bernhard Justice- Salt Hot Tub - 100+ Wifi - Gas Firepl - Bikes - Ev Plug - Walkable are the best vacation rentals with a pool in Bend, OR.
When is the best time to book a vacation rental in Bend, OR?
The best time to book is during the shoulder season, from April to May or September to October. You'll avoid the summer crowds and the prices are usually lower.
What are the best rentals for families and kids in Bend, OR?
The best rentals for families and kids in Bend, OR are Cozy Bookworm's Retreat In Bend, Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub and Historic Belle Millhouse In Bend - Or - Walk To Downtown -vrbo.
What are the best budget-friendly activities in Bend, OR?
The Deschutes River is perfect for a free day of swimming, sunbathing, or kayaking. You can also walk or cycle the Deschutes River Trail, which stretches for 23 km along the river. And there are plenty of free concerts and events happening in the city throughout the year.
What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?
The best vacation rentals or Airbnb with a jacuzzi in Bend, OR are The Garden Apt-hot Tub Fireplace Ac 250+ Mbps, Tranquil & Magical-hottub Fireplace Ac 250 Mbps+ and Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub.
What are the best restaurants with local dishes in Bend, OR?
Try the Anthony's at the Old Mill, they have a great selection of fresh seafood and local dishes. There's also The Pine Tavern, it's a classic Bend restaurant with a menu full of local favourites.
What are the best walking or cycling routes in Bend, OR?
The Deschutes River Trail is a great option for both walking and cycling, you can also check out the Tumalo Creek Trail, it's a beautiful trail that winds through the forest.
Are there pet-friendly attractions in Bend, OR?
Yes, many of the parks and trails in Bend are pet-friendly, including the Drake Park and the Deschutes River Trail. There are also a number of restaurants and shops that welcome dogs.
What are the benefits of choosing a vacation rental in Bend, OR?
Vacation rentals offer more space and privacy than a hotel, and they often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
What are the top sports attractions and facilities in Bend, OR?
Bend is a great place for outdoor sports, with plenty of opportunities for hiking, biking, skiing, and snowboarding. The Mount Bachelor Ski Resort is a popular destination for winter sports, and there are also several golf courses in the area.

Popular destinations

Best Bend, OR vacation rentals with jacuzzi

10 2 reviews

Private Hot-tub- 3 Bdr For 8 Pet's Ok

house, Bend

This Bend holiday home is located 4.3km from Hollinshead Park, 5.3km from Drake Park, and 7.2km from Ponderosa Park, offering easy access to Bend's popular green spaces.
The 172 square metre property boasts three bedrooms sleeping up to eight guests, three bathrooms, a fully equipped kitchen, a private hot tub, a garden, and free Wi-Fi; perfect for families or groups exploring Bend's cycling routes and attractions.

5.5 2 reviews

Fam-friendly- Hot-tub - 30min To Mt Bachelor

house, Bend

This three-bedroom Bend holiday home is situated 4km from Drake Park and 3.2km from Ponderosa Park, offering easy access to Bend's amenities and a 30-minute drive to Mount Bachelor.
The 156-square-metre property boasts three bathrooms, a Jacuzzi, a garden, parking, and can comfortably accommodate up to 15 guests, featuring a fully equipped kitchen and free Wi-Fi.

10 2 reviews

84 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Bend

This two-bedroom apartment in Mt. Bachelor Village Resort is situated minutes from Bend's city centre and offers easy access to outdoor activities such as skiing and hiking.
The 77-square-metre condo features a well-equipped kitchenette, two bathrooms, a private balcony, and access to a seasonal swimming pool and hot tub, accommodating up to six guests.

No reviews

28 M² Condo ∙ 1 Bedroom ∙ 2 Guests

apartment, Bend

This studio flat is situated in Mt. Bachelor Village, offering convenient access to the Deschutes River Trail, and is only a short drive from downtown Bend and the Old Mill District, with Mt. Bachelor located 30 kilometres away.
This 27 square metre studio apartment accommodates two guests and features a king-size bed, a mini-fridge, microwave, and coffeemaker, with access to a seasonal swimming pool, year-round hot tub, playground, and games room.

Best Bend, OR vacation rentals with parking

9.9 189 reviews

New Tranquil Retreat On Canal

house, Bend

This renovated guest house near Pine Nursery Park in Bend, Oregon, is conveniently located 8 kilometres from the city centre and under 32 kilometres from Redmond Municipal Airport.
Sleeping up to six guests, this self-catering property boasts a fully equipped kitchen, in-unit laundry, a large bathtub, balcony, smart TV, and board games, making it ideal for families seeking a peaceful retreat in a secluded setting on a 1.2-hectare plot by a canal.

10 135 reviews

River Views At First Street Rapids + Walk Downtown

apartment, Bend

This ground floor studio flat is located in a residential area just 0.8 kilometres from downtown Bend and 1.4 kilometres from Drake Park, offering a peaceful setting close to the city's attractions. The property enjoys excellent user, location and cleanliness ratings, making it a popular choice for travellers. The flat is a studio apartment for two guests, equipped with a kitchenette and a queen-size bed. It includes a range of amenities such as a swimming pool, hot tub, laundry facilities, and parking, along with easy access to the river trail, making it ideal for exploring Bend's outdoor activities.

9.9 125 reviews

Zen W/ Hot Tub, Office, Yard, Dog Friendly, Park

apartment, Bend

This Bend property is conveniently located a short drive (approximately 8km) from Costco and Whole Foods, and minutes from downtown Bend, the Deschutes River, Pilot Butte State Scenic Viewpoint, and numerous trails and parks.
This 167 square metre house boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, jacuzzi, fitness centre, and a large private garden with a firepit; perfect for families or groups exploring Bend.

10 23 reviews

High Desert Haven | Dogs Stay Free

apartment, Bend

This modern desert retreat is located in a desert district, offering a private yard and convenient access to local attractions.
This pet-friendly one-bedroom suite accommodates two guests, featuring a private outdoor space, modern interior design, and an ensuite bathroom.

Compare Vacation Rentals & Airbnb in Bend, OR

3745 Rentals and Airbnb in Bend, OR