Vacation rentals in Bend, OR

3745 available vacation rental offers

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Bend, OR vacation rentals
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Best Vacation rentals and Airbnb offers in Bend, OR

Best family friendly Bend, OR vacation rentals

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

Condo ∙ 1 Bedroom ∙ 2 Guests - Bend, OR
8.0 1 review

Condo ∙ 1 Bedroom ∙ 2 Guests

apartment, Bend
This king suite is located in Mount Bachelor Village, Bend, Oregon, within walking distance of the Old Mill District and the Deschutes River Trail.
The one-bedroom, one-bathroom unit sleeps two guests and features a kitchenette with a coffee maker, mini-fridge, and microwave, plus access to a seasonal outdoor pool (March-September), two year-round hot tubs, and a 10% discount for weekly bookings (excluding Christmas/New Year's).
170 M² House ∙ 3 Bedrooms ∙ 6 Guests - Bend, OR
9.8 20 reviews

170 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Bend
This Bend vacation home sits at the base of Pilot Butte, offering immediate access to hiking trails and is minutes from Whole Foods and other restaurants.
The 1820-square-foot property features three bedrooms, three bathrooms, accommodates six guests, and includes a gourmet kitchen, hot tub, and a second-level office space.
New! Cozy Bend Escape | Hot Tub | Forest Views - Bend, OR
10 3 reviews

New! Cozy Bend Escape | Hot Tub | Forest Views

apartment, Bend
This upper-level, corner condo in Mt. Bachelor Village Resort's Ski House 3 is located in Bend's Century West neighborhood, offering mountain and river proximity, with Pilot Butte State Park approximately 1 mile away.
This 850 sq ft condo accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, a natural gas fireplace, a king main suite, ductless air conditioning, and access to a community hot tub and seasonal swimming pool.
Gateway To Mt Bachelor - Bend, OR
9.8 173 reviews

Gateway To Mt Bachelor

house, Bend
This Bend vacation home is conveniently located just 2.4 miles from Drake Park and 4.6 miles from Hollinshead Park, making it easy to explore the city's attractions and enjoy the surrounding natural beauty. This property consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The 850 square foot house comfortably accommodates up to 6 guests with two bathrooms. The home is fully equipped with modern amenities like air conditioning, a private pool, a jacuzzi, a terrace, a garden, and free parking, making it an ideal choice for a relaxing and enjoyable stay in Bend.

Best Bend, OR vacation rentals with a fireplace

The Drake Club, Walk To Downtown Ev Charger - Bend, OR
9.6 678 reviews

The Drake Club, Walk To Downtown Ev Charger

cabin, Bend
This Westside Bend studio apartment is conveniently located an 8-minute walk from downtown Bend, a 10-minute walk from the Old Mill District, and a short bike ride from Phil's Trail.
The pet-friendly unit offers a fully equipped kitchen, one bathroom, sleeps two guests, includes cable TV and Wi-Fi, a fenced yard, and access to an EV charger; rentals of bikes and paddleboards are also available.
Downtown, Modern Nostalgia--walk To Shops, Cafes - Bend, OR
9.8 536 reviews

Downtown, Modern Nostalgia--walk To Shops, Cafes

apartment, Bend
This charming Bend cottage is located on the Westside, just a five-minute walk from the Deschutes River and a ten-minute walk to downtown, making it easy to explore the city's attractions and enjoy the beautiful natural surroundings. Guests consistently rate this property excellent for location, cleanliness, and overall experience.
This 1000-square-foot cottage comfortably sleeps six guests in its two bedrooms and two bathrooms. Enjoy modern amenities like free Wi-Fi, cable TV, a fully equipped kitchen, and a private terrace, perfect for relaxing after a day of exploring Bend's breweries, hiking trails, and outdoor activities.
Wanderlust Condo Bend - Fully Remodeled! - Bend, OR
10 19 reviews

Wanderlust Condo Bend - Fully Remodeled!

apartment, Bend
Wanderlust Condo Bend, located in Mt. Bachelor Village, offers easy walking access to the Old Mill District, the Deschutes River Trail, and Mt. Bachelor Ski Resort.
This newly remodeled 840-square-foot condo features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, in-unit laundry, a private patio, and access to a pool, hot tub, and BBQs.
Location, Style And Comfort - Bend, OR
10 1 review

Location, Style And Comfort

apartment, Bend
This historic house is centrally located between the Deschutes River and downtown Bend, offering easy access to both natural beauty and urban amenities.
This 3-bedroom, 1-bathroom rental accommodates up to 5 guests and features a private fenced backyard, a fireplace, and high-end appliances.

Frequently Asked Questions about vacation rentals in Bend, OR

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

    Bend is known for its outdoor adventures. You can't miss a hike up Pilot Butte for panoramic views of the city and Cascade Mountains. For a more challenging hike, try the Smith Rock State Park, famous for its rock climbing. And don't forget to visit the Old Mill District for shopping, dining, and the Deschutes River.
  • What are the best Airbnb and vacation rentals in Bend, OR?

    Private Apt - 1bdrm/1bath - With Kitchen - 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, with its proximity to restaurants, shops, and the Deschutes River. If you're looking for a quieter stay, consider the Westside, close to the Cascade Lakes Highway and offering easy access to hiking trails and lakes. The downtown area is also a good option, offering a vibrant nightlife and a central location.
  • What are the most popular Airbnbs in Bend, OR?

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

    The High Desert Museum is a must-visit for families, showcasing the natural history and wildlife of the region. For a fun day out, head to the Sunriver Nature Center & Observatory for a guided tour of the night sky. The Pilot Butte State Scenic Viewpoint is a great spot for kids to run around and enjoy the views.
  • What are the best vacation rentals with a pool in Bend, OR?

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

    Peak season in Bend runs from June to September, so it's best to book your vacation rental well in advance, especially if you're traveling during summer holidays. You'll find better deals and more availability during the shoulder seasons, like spring and fall.
  • What are the best rentals for families and kids in Bend, OR?

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

    Bend is full of free and low-cost activities. Take a stroll along the Deschutes River Trail, enjoy a picnic at Drake Park, or explore the many free art galleries in the downtown area. You can also check out the free events at the Les Schwab Amphitheater, like outdoor concerts and movies.
  • What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?

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

    For a taste of Bend, try the classic Bend Brewing Co. for their craft beers and pub fare. Anthony's at the Old Mill offers fresh seafood with a beautiful view of the Deschutes River. And for a casual dining experience, head to the popular 10 Barrel Brewing Co. for their craft beers and delicious burgers.
  • What are the best walking or cycling routes in Bend, OR?

    The Deschutes River Trail is a scenic and easy walk or bike ride, offering views of the river and the Cascade Mountains. For a more challenging ride, try the Century Drive, a 40-mile loop around Bend that takes you through forests, meadows, and past the Cascade Lakes.
  • Are there pet-friendly attractions in Bend, OR?

    Many parks and trails in Bend are dog-friendly, including the Deschutes River Trail and Drake Park. The High Desert Museum also welcomes well-behaved dogs on leash. Many restaurants offer outdoor seating where you can bring your furry friend.
  • What are the benefits of choosing a vacation rental in Bend, OR?

    Vacation rentals offer more space and privacy than hotels, often with kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups. Many rentals are located in desirable neighborhoods, offering easy access to attractions and activities.
  • What are the top sports attractions and facilities in Bend, OR?

    Bend is a popular destination for outdoor sports. The area offers world-class skiing and snowboarding at Mount Bachelor in the winter. In the summer, you can enjoy hiking, biking, kayaking, and fishing. The Bend Golf Club is a public course with stunning views of the Cascade Mountains.

Popular destinations

Choose the Perfect Vacation Rentals with a Hot Tub in Bend, OR

Experience the ultimate recovery after a long active day with a private hot tub at these premier Bend, OR vacation rentals.

Riverfront Condo Next To Park And Downtown Bend - Bend, OR
8.6 34 reviews

Riverfront Condo Next To Park And Downtown Bend

apartment, Bend
This second-story condo in Bend's River West neighborhood offers river views and is a 10-minute walk to downtown attractions.
This 640 sq ft condo accommodates up to 4 guests with two queen beds, features a full kitchen, indoor pool, hot tub, and is pet-friendly for up to two pets with an additional fee.
Mountain Daydream West Bend Condo With Pool! - Bend, OR
10 6 reviews

Mountain Daydream West Bend Condo With Pool!

apartment, Bend
This newly remodeled Westside Bend condo provides a modern-cabin feel with vaulted ceilings and a gas fireplace, offering keyless entry and a private balcony overlooking a pine forest, just a short walk from the Deschutes River and a quick drive to Mt. Bachelor.
This family-friendly, pet-friendly condominium accommodates up to 6 guests with 2 bathrooms and a fully equipped kitchen, featuring access to community amenities like a swimming pool, hot tubs, playground, and fire pit, and is conveniently located near the Old Mill, Downtown Bend, and Hayden Homes Amphitheater.
Near Old Mill! Family Home W/hot Tub & Trampoline - Bend, OR
9.9 73 reviews

Near Old Mill! Family Home W/hot Tub & Trampoline

apartment, Bend
This Bend, Oregon house rental is centrally located near the Old Mill District, within walking distance of the Deschutes River Trail and a short bike ride from Hayden Homes Amphitheater.
This 1800-square-foot property boasts three bedrooms, two bathrooms, sleeps up to ten guests, and features a well-equipped kitchen, a jacuzzi, and outdoor amenities including an inflatable hot tub, cold plunge tub, trampoline, and ninja course.
Walk To Downtown - Near River - Bend, OR
9.8 200 reviews

Walk To Downtown - Near River

apartment, Bend
This charming cottage is located just one block from the Deschutes River and five blocks from downtown Bend, placing you within easy reach of the city's best attractions and the natural beauty of the area. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy a private hot tub, a fenced yard perfect for pets, and easy access to Drake Park, the Deschutes River, and the vibrant downtown area with its shops, restaurants, and entertainment options.

Best Bend, OR vacation rentals with parking

River View Condo- Edge Of Downtown - Bend, OR
No reviews

River View Condo- Edge Of Downtown

house, Bend
This condo is located on the edge of downtown Bend, a 15-minute walk from Drake Park and 1.3 miles from Hollinshead Park.
This 640 sq ft condo accommodates up to 7 guests and features air conditioning, a full kitchen with a dishwasher, a fireplace, an indoor pool, a hot tub, and on-site parking.
Atomic Ranch ~ Mcm In Bend ~ Hot Tub + Huge Yard - Bend, OR
No reviews

Atomic Ranch ~ Mcm In Bend ~ Hot Tub + Huge Yard

apartment, Bend
This remodeled mid-century modern home is situated in Bend's Westside district, offering direct access to nearby trails and a short 5-minute drive to Riverbend Park and the Deschutes River, with Mt. Bachelor ski resort 21 miles away.
This 1430 sq ft house accommodates up to 8 guests across 3 bedrooms, featuring a private backyard with a hot tub and playset, a fully equipped designer kitchen, complimentary bikes, laundry facilities, and a small gym, making it ideal for families and pet owners.
Adorable 3 Bdrm 1/2 Mile From Downtown & Old Mill - Bend, OR
9.7 87 reviews

Adorable 3 Bdrm 1/2 Mile From Downtown & Old Mill

apartment, Bend
This Bend, Oregon mill is ideally located near downtown, the Old Mill District, and Hayden Amphitheater, offering easy access to the Deschutes River and Mount Bachelor (a 25-minute drive).
This three-bedroom, one-bathroom house sleeps five guests and features a kitchen with a fridge, microwave, and dishwasher, a jacuzzi, a fenced yard, and parking; the loft provides extra sleeping space.
Modern Retreat · Walk To Old Mill · Sleeps 6 - Bend, OR
9.4 115 reviews

Modern Retreat · Walk To Old Mill · Sleeps 6

apartment, Bend
This Old Mill Retreat is a family-friendly Bend, Oregon rental located a short walk from the Old Mill District, providing easy access to shops, restaurants, and Highway 97 for day trips to Smith Rock State Park, Sunriver, and Mount Bachelor.
This 1,250-square-foot house features two bedrooms, two bathrooms, sleeps six (with options for more), and boasts three private patios, a fully equipped kitchen, in-home laundry, Wi-Fi, and proximity to river trails and breweries.

Top 5-Star Vacation Rentals in Bend, OR

These upscale vacation rentals in Bend, OR offer premium amenities and refined service for an unforgettable stay.

Stylish Cozy Bungalow W/ Theater - Bend, OR
9.8 161 reviews

Stylish Cozy Bungalow W/ Theater

apartment, Bend

Guest-Favorite Pet-Friendly Vacation Rentals in Bend, OR

Bring the whole family to Bend, OR with pet-friendly vacation rentals that offer comfort for your dog.

Spacious New Remodel In Quiet Neighborhood. - Bend, OR
10 3 reviews

Spacious New Remodel In Quiet Neighborhood.

apartment, Bend
217 M² House ∙ 3 Bedrooms ∙ 8 Guests - Bend, OR
10 6 reviews

217 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Bend
Riverview Pet Friendly Condo In Downtown Bend - Bend, OR
9.2 10 reviews

Riverview Pet Friendly Condo In Downtown Bend

apartment, Bend
Modern Guesthouse  Walk To Old Mill + River Trail - Bend, OR
10 114 reviews

Modern Guesthouse Walk To Old Mill + River Trail

bungalow, Bend

Browse Vacation Rentals with Swimming Pool in Bend, OR

Enjoy a swim whenever you like; these Bend, OR vacation rentals come with an on-site swimming pool.

Villa #5 At Broken Top - Bend, OR
9.5 208 reviews

Villa #5 At Broken Top

house, Bend
Pool, Ac, Close To Amphitheater & Old Mill - Bend, OR
10 141 reviews

Pool, Ac, Close To Amphitheater & Old Mill

apartment, Bend
Upper-level, Newly Remodeled With Mbvr Amenities! - Bend, OR
9.7 20 reviews

Upper-level, Newly Remodeled With Mbvr Amenities!

apartment, Bend
Riverfront Studio With Trail Access - Bend, OR
9.3 3 reviews

Riverfront Studio With Trail Access

studio, Bend
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