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

Private Balcony And Resort Amenities - Cozy Inviting Escape

apartment, Bend

This two-bedroom apartment is situated within the Mt. Bachelor Village Resort, offering convenient access to downtown Bend and outdoor recreation areas, just a short drive from skiing, water sports, golf, and hiking.
This family-friendly condo sleeps six guests and features a well-equipped kitchenette, a gas fireplace, a private balcony, and access to resort amenities including a seasonal swimming pool and hot tub.

9.8 37 reviews

Great Deals Next Summer During Deck Construction.

apartment, Bend

This two-bedroom Bend apartment, ideally located for access to Mount Bachelor, offers proximity to Bend's town centre and various outdoor pursuits.
The self-catering property sleeps six, boasting a fully equipped kitchen, two bathrooms (one with a washer/dryer), a private hot tub with Bend views, and access to a swimming pool, jacuzzi and garden.

9.9 195 reviews

Close, Cute & Clean! Hot Tub Bend Adventure Base

apartment, Bend

This two-bedroom apartment is conveniently located in Bend, just a short walk from the Old Mill District and the Deschutes River, providing easy access to the town's attractions and amenities. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment comfortably sleeps four guests with a queen bed and a full-over-twin trundle bed. Guests can enjoy a fully equipped kitchen, a private patio with a hot tub and fire pit, and access to a fitness centre, a garden, and parking.

9.7 117 reviews

Bekind Cottage

house, Bend

BEkiND Cottage is situated in Bend, Oregon, a short walk (approximately 1.6 km) from Drake Park and a few miles (approximately 5 km) from Hollinshead and Ponderosa Parks.
This 94 square metre house offers three bedrooms, one bathroom, a well-equipped kitchen including a dishwasher, a jacuzzi, a terrace, a garden, free parking, and free Wi-Fi; nearby activities include skiing and tennis on the on-site court.

8.6 8 reviews

Wilderness Exploration | 2 Queens + Ada Rated

apartment, Bend

This Boyd Acres apartment is situated near the Bend River Promenade and Deschutes River, within 1.6km of Sun Mountain Fun Center and River's Edge Golf Course.
This self-catering flat offers one bathroom, sleeps four guests, and includes an indoor pool, hot tub, free Wi-Fi, and essential kitchen amenities; limited housekeeping is provided.

10 99 reviews

Daphne Farmhouse...a Welcome Home Kind Of Feeling!

apartment, Bend

This Bend farmhouse, situated 2.4 kilometres from St Charles Bend and minutes from Pilot Butte State Scenic Viewpoint, offers easy access to the Old Mill District and Bend city centre.
The 3-bedroom property, sleeping up to 5 guests, features a full kitchen, laundry facilities, high-speed Wi-Fi, cable TV, a private basketball court, and ample outdoor seating on a large patio within its 0.6-acre grounds.

9.7 267 reviews

A Stone's Throw | Riverside Condo - Top Floor

apartment, Bend

This Westside Bend apartment, situated a short distance (less than 0.5 km) from downtown Bend and the Deschutes River, offers easy access to Pioneer Park and the Bend River Trail.
The top-floor condo sleeps four, features two bathrooms, a fully equipped kitchen with balcony gas grill, high-speed internet, Roku Live TV, and family-friendly amenities including a Pack & Play crib and high chair.

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.

No reviews

Pet Friendly Riverside Studio In Downtown Bend

apartment, Bend

This ground-floor studio flat offers direct access to the Deschutes River Trail, with Pioneer Park adjacent and downtown Bend just a short walk away, ensuring you are close to both nature and amenities.
This accommodation welcomes up to two guests and two pets for an additional fee, featuring a kitchenette with a stovetop, mini-fridge, and microwave, plus access to a heated indoor swimming pool and hot tub.

10 108 reviews

Quail View-pets Welcome, Great Outdoor Space

house, Bend

This executive suite, located in a peaceful Bend cul-de-sac, offers easy access to Bend's attractions, although precise distances to landmarks aren't specified.
The pet-friendly property boasts a spacious layout with one bathroom, accommodating two guests, and features a private patio, shared deck with gas grill, big-screen TV, work desk, fully equipped kitchen with dishwasher and gas range, washer/dryer, and ample off-street parking.

10 165 reviews

Charming Millhouse W/ Hot Tub Close To Everything

apartment, Bend

This Bend Old Mill District cottage, a short walk from restaurants and the Deschutes River, is conveniently located near the Hayden Homes Amphitheatre and approximately 48km from Mount Bachelor.
This pet-friendly two-bedroom house sleeps four, offering two king-size beds, a fully equipped kitchen with a gas BBQ, a hot tub, and two bicycles for exploring the area, alongside board games and other entertainment options.

9.7 76 reviews

Frosty Summit Condo, Mount Bachelor W/ Pool

apartment, Bend

This Mount Bachelor Village condo offers stunning views of the wooded hillside and Deschutes River, a short drive (approximately 8 km) from Bend city centre and Mount Bachelor ski area.
The one-bedroom apartment sleeps two guests, boasting a full kitchen, private balcony, shared pool and hot tub access, plus a queen-sized bed and streaming TV.

Best family friendly Bend, OR vacation rentals

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

10 12 reviews

New Renovated - 4 Br, 2 Bath - 0,9m To Old Mill

apartment, Bend

This Bend apartment, located in an established neighbourhood a short distance from the Old Mill District and Bend city centre, offers easy access to attractions such as Deschutes Brewery and Drake Park.
Sleeping six guests, this four-bedroom, two-bathroom property features a fully renovated kitchen, high-speed WiFi (300 Mbps), a large patio, and ample storage, perfect for families or groups exploring Bend, Oregon.

9.8 17 reviews

New! Hot Tub~foosball~bonus Room~pup Friendly!

apartment, Bend

This Bend, Oregon holiday home is conveniently located near Mount Bachelor Ski Resort and Deschutes National Forest, offering easy access to Widgi Creek Golf Club and Sun Mountain Fun Center.
This four-bedroom, three-bathroom property sleeps ten guests and boasts a private hot tub, a fully equipped kitchen with stainless steel appliances, a games room with a foosball table, and pet-friendly amenities including an extra-large dog crate.

9.7 58 reviews

Cozy Sunshine Retreat In Bend

apartment, Bend

This detached house in Bend offers excellent access to downtown amenities, being just a few minutes' drive away, and is conveniently located for exploring Central Oregon's outdoor pursuits.
This property accommodates up to six guests across three bedrooms and three bathrooms, featuring a fully equipped kitchen, a private hot tub in a fenced garden, a dedicated home office, and multiple living areas for comfort.

9.8 17 reviews

A Stone's Throw - Westside Vibes

apartment, Bend

This three-bedroom flat in Bend's Westside district is situated just 160 metres from Galveston Street and a short walk to the Deschutes River, offering convenient access to downtown attractions.
This pet-friendly accommodation for up to six guests boasts a private wrap-around deck with a propane barbecue, a saltwater hot tub, a fully equipped kitchen, and complimentary high-speed WiFi.

Best Bend, OR vacation rentals with a fireplace

9.6 111 reviews

New Listing! Private Hot Tub | Backyard | Foosball

apartment, Bend

This Bend riverfront property is located within 1.6km of Bend Factory Stores and the Old Mill District, and close to the Deschutes River and Riverbend Dog Park.
This five-bedroom, 197 square metre house sleeps ten guests and boasts a fully equipped kitchen, jacuzzi, private fenced yard, and barbecue grills, perfect for families or groups exploring Bend.

9.8 343 reviews

A Stone's Throw | Elderberry - Salt Water Hot Tub

bungalow, Bend

This family-friendly house is located in Bend, just a kilometre from Drake Park, the Deschutes River, and Tower Theater, and within a 2 kilometre radius of the Des Chutes Historical Museum and Downtown Bend Business Association. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house spans 102 square metres and comfortably accommodates eight guests. It features a fully equipped kitchen, a private garden, a swimming pool, a jacuzzi, a spa, a fitness centre, a tennis court, and parking.

9.4 35 reviews

Walk To Downtown And Amphitheater

apartment, Bend

This Westside Bend apartment, a short 0.8km walk from Drake Park and downtown Bend, offers easy access to numerous breweries, restaurants, and attractions including the Deschutes Brewery and Regal Old Mill cinema.
The 88 square metre property features two bedrooms, one bathroom, sleeps four comfortably in a queen and a double bed, and includes a fully equipped kitchen with dishwasher, air conditioning, parking, and high-speed internet access.

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.

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 6 reviews

Bluebird Day - Casa Sol

house, Bend

Bluebird Day - Casa Sol, a pet-friendly house in Bend, Oregon, is located an 8-minute walk (approximately 0.6 km) from Drake Park and a short drive from Hollinshead and Ponderosa Parks.
This two-bedroom, two-bathroom property sleeps up to nine guests and boasts a fully equipped kitchen with fridge, microwave, and dishwasher, plus a jacuzzi, air conditioning, free Wi-Fi, and on-site parking; it is conveniently situated 26 km from Redmond Municipal Airport.

9.4 3 reviews

Bend Condo Near Mt Bachelor With Hot Tub Sleeps 6

apartment, Bend

This two-bedroom apartment in Mount Bachelor Village Resort is situated a short drive (a few kilometres) from Bend city centre, the Old Mill District, and Mount Bachelor Ski Resort, offering easy access to local attractions.
The 78-square-metre property features an open-plan living area with a fireplace, a private balcony with mountain views, a well-equipped kitchen, and a swimming pool, jacuzzi and parking, comfortably sleeping six guests.

8.0 2 reviews

Broken Top Hot Tub Condo Near Old Mill Sleeps 6

apartment, Bend

This Bend apartment, situated in the Century West neighbourhood, is 0.3km from the Broken Top Club and a short drive from the Old Mill District (4km) and Mount Bachelor (32km).
The 161 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, jacuzzi, private deck with hot tub, and access to community amenities such as a playground and ski storage.

10 20 reviews

Deschutes Riverfront Zen Retreat

apartment, Bend

This ground-floor studio apartment is situated just 320 metres from downtown Bend, offering convenient walking access to the Deschutes River trail, Pioneer Park, and Drake Park.
This studio accommodation for two guests features a kitchenette with a fridge, freezer, and microwave, air conditioning, Wi-Fi, and access to an indoor swimming pool and hot tub, with a soaking tub and shower for relaxation.

Best Bend, OR vacation rentals with parking

9.4 63 reviews

Riverside Cottage - Just Steps From The Deschutes

apartment, Bend

This riverside flat in Bend's River West district offers direct access to the Deschutes River and is just a short walk to downtown attractions.
This 42 square meter flat accommodates up to four guests, features a kitchenette, air conditioning, and access to an indoor heated swimming pool and Jacuzzi, with pets welcome for an additional fee.

9.8 314 reviews

Charming Mt. Bachelor Village Condo

house, Bend

This newly renovated apartment is located in the Mt. Bachelor Village Resort on the west side of Bend, just a short walk from the Deschutes River trail and The Old Mill. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is a comfortable dwelling with two bedrooms, each with a queen-sized bed, and a queen-sized sofa bed in the living area, accommodating up to six guests. Guests can enjoy a fully equipped kitchen, a gas grill on the back deck, a swimming pool (seasonal), a year-round hot tub, and a growler for exploring the local craft beer scene.

9.4 45 reviews

Pet Friendly Riverside Studio In Downtown Bend

apartment, Bend

This ground-floor Bend studio apartment boasts unparalleled river views, situated directly on the Deschutes River Trail.
Offering easy access for all, this pet-friendly self-catering unit sleeps two, includes a kitchenette, indoor heated pool and hot tub access, and is close to Bend's attractions.

9.5 148 reviews

Larkspur Trail - Pool Table, Outdoor Living

apartment, Bend

Larkspur Trail is located in Bend, a short distance from Hollinshead Park (5.1 km) and Drake Park (6.1 km), offering easy access to the city’s attractions and outdoor activities. This property has received excellent ratings for location, cleanliness, and user experience.
This three-bedroom home provides spacious accommodation for families or groups of friends. Enjoy the private heated pool, patio, fully equipped kitchen, and fitness centre, as well as free parking and Wi-Fi.

Compare Vacation Rentals & Airbnb in Bend, OR

3745 Rentals and Airbnb in Bend, OR

Private Balcony And Resort Amenities - Cozy Inviting Escape

Great Deals Next Summer During Deck Construction.