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

Ranch Guesthouse | King Bed - Bend, OR
9.6 10 reviews

Ranch Guesthouse | King Bed

house, Bend
This private studio guesthouse is located in Bend's Westside district, one block from Newport and Galveston Avenues, and a 5-minute drive to downtown Bend.
This dog-friendly accommodation sleeps up to 4 guests with a king bed and a pull-out sofa, featuring a full kitchen, in-unit laundry, and a yard with a firepit, with Phil's Trail 10 miles away and Mt. Bachelor 25 miles away.
Serenity Retreat | Pool, Spa, Trails & Mt Bachelor - Bend, OR
9.9 116 reviews

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

apartment, Bend
This three-bedroom, two-bathroom lodge is situated in the River Wild area of Mount Bachelor Village, a short drive from Bend's city center and close to Mount Bachelor, Phil's Trail, and the Deschutes River.
The 3-bedroom, 2-bathroom home offers a rustic-elegant design with cathedral ceilings, a stone fireplace, a wrap-around porch, a detached two-car garage, and access to a community pool and spa; it sleeps six guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher.
81 M² Condo ∙ 1 Bedroom ∙ 4 Guests - Bend, OR
10 9 reviews

81 M² Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Bend
This Westside Bend apartment, Deschutes Nest, is ideally located two blocks from the Deschutes River and within walking distance of the Old Mill District, downtown Bend, and the Hayden Homes Amphitheater.
The 860-square-foot unit features one bedroom, one bathroom, sleeps four with a queen bed and sleeper sofa, and includes amenities such as a full kitchen, in-unit laundry, and a 10% discount for weekly bookings (excluding holidays).
Spacious Condo In Bend! Prime Location! - Bend, OR
10 3 reviews

Spacious Condo In Bend! Prime Location!

apartment, Bend
This Mount Bachelor Village Resort condo is conveniently located in Bend, Oregon, a short drive from downtown, the Old Mill District, and Mount Bachelor Ski Resort.
This 830-square-foot vacation rental boasts three bedrooms, one bathroom, and sleeps six guests comfortably, featuring a fully equipped kitchen, private balcony, and access to resort amenities including a pool, jacuzzi, and a fitness center.

Best Bend, OR vacation rentals with a fireplace

Sunny Getaway: Fenced | Near Trails, Dining, Music - Bend, OR
9.8 264 reviews

Sunny Getaway: Fenced | Near Trails, Dining, Music

bungalow, Bend
This Southeast Bend cottage, near great dining and shopping with easy access to the Deschutes River Trail and breweries, offers a convenient location for exploring Bend's attractions.
This family-friendly rental sleeps six, features a fully fenced yard, private deck, in-unit laundry, and a fully equipped kitchen with a dishwasher, making it perfect for a Bend getaway.
Bluebird Day - Aspen Getaway, A Cozy 1-bedroom Retreat In Bend, Or. - Bend, OR
9.6 15 reviews

Bluebird Day - Aspen Getaway, A Cozy 1-bedroom Retreat In Bend, Or.

apartment, Bend
This downtown Bend apartment, a short walk from the Old Mill District, Hayden Homes Amphitheater, and the Deschutes River, offers easy access to numerous restaurants and breweries.
This 570-square-foot rental boasts two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, private patio with a gas fire pit, large fenced yard, and HDTV with streaming services.
Sandalwood Suite - Bend, OR
9.8 10 reviews

Sandalwood Suite

house, Bend
This 800 sq ft cottage in Bend is located in a residential area, a short walk from Pine Nursery Park and three minutes from St. Charles Hospital.
This pet-friendly rental offers a full kitchen, laundry room, and off-street parking for one vehicle, accommodating up to four guests with a sleeper sofa and a spacious private side yard.
Quinn Creek - Bend, OR
9.9 170 reviews

Quinn Creek

house, Bend
This vacation home in Bend's west side is within 3 miles of Westside Church, Central Oregon Community College, and Drake Park. It has excellent user, location, and cleanliness ratings.
The house has 4 bedrooms and a sofa bed, accommodating up to 8 guests. It has a floor area of 3240 square feet. Guests can enjoy a water park, barbecue grills, a swimming pool, a terrace/balcony, a garden, a spa, a fitness center, a tennis court, and parking. They can also relax by the fireplace and enjoy a fully equipped kitchen with a refrigerator and oven.

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.

Bend, Hottub, Resort Amenities, Dogs Ok, W/d, Wifi - Bend, OR
9.6 7 reviews

Bend, Hottub, Resort Amenities, Dogs Ok, W/d, Wifi

apartment, Tetherow
This smoke-free vacation home is located in Bend, just 1.1 miles from the Deschutes River and within a 3-mile radius of Deschutes Brewery and the Old Mill District. The property has received excellent user ratings, making it a popular choice for travelers.
The Sunny Vacay rental is a spacious 2,700 square foot home that can comfortably accommodate up to 10 guests. Enjoy a relaxing dip in the outdoor pool, stay active in the fitness center, unwind in the sauna, and indulge in a relaxing soak in the spa tub.
Toasty Hot Tub + Firepit ~ Mt. Bachelor ~ Dogs Ok - Bend, OR
9.4 8 reviews

Toasty Hot Tub + Firepit ~ Mt. Bachelor ~ Dogs Ok

apartment, Tetherow
This family-friendly vacation home is located in Bend, just a short drive from the Deschutes River, Deschutes Brewery, Bend Rock Gym, and the Old Mill District. The home has received excellent user, location, and cleanliness ratings.
This spacious five-bedroom vacation rental spans 2,740 square feet and comfortably accommodates up to 10 guests. Enjoy a private pool, fitness center, sauna, spa tub, and a relaxing garden, along with modern amenities like free Wi-Fi, a fireplace, and a fully equipped kitchen.
Riverfront Condo Next To Park And Downtown Bend - Bend, OR
9.3 3 reviews

Riverfront Condo Next To Park And Downtown Bend

house, Bend
This riverfront vacation rental in Bend is a 15-minute walk from Drake Park and 1.3 miles from Hollinshead Park.
This 640 sq ft, 1-bedroom condo accommodates up to 7 guests and features a full kitchen, fireplace, air conditioning, a swimming pool, and a hot tub, with complimentary parking and WiFi.
Great For Groups, Resort, Shuttle, Garage, Dogs Ok - Bend, OR
9.6 16 reviews

Great For Groups, Resort, Shuttle, Garage, Dogs Ok

apartment, Tetherow
This smoke-free vacation home in Bend is located just a short distance from the Deschutes River and Deschutes Brewery, offering easy access to outdoor activities and local attractions. This property has earned excellent user ratings, making it a popular choice for travelers.
The spacious 5-bedroom home, with a floor area of 2850 square feet, comfortably accommodates up to 10 guests. Enjoy a relaxing stay with amenities like an outdoor pool, fitness center, sauna, and a fully equipped kitchen, perfect for preparing meals and enjoying the peaceful garden.

Best Bend, OR vacation rentals with parking

Rustic Cottage With Views Of The Deschutes River! - Bend, OR
9.4 18 reviews

Rustic Cottage With Views Of The Deschutes River!

apartment, Bend
This studio cottage in River West, Bend, offers direct access to the Deschutes River with panoramic rapids views and is within a 0.5 mile walk to downtown Bend's shops, restaurants, and the Tower Theater.
This 320 sq ft pet-friendly accommodation for two features custom juniper furniture, a kitchenette with a fridge and microwave, air conditioning, an indoor swimming pool, and keyless entry.
Cascade Mountain Views - Bend, OR
10 18 reviews

Cascade Mountain Views

apartment, Bend
This single-level mid-century modern house in a quiet SE Bend residential neighborhood offers mountain views and is 2 miles from Old Mill, 2 miles from downtown Bend, and 30 minutes from Mt. Bachelor ski resort.
This 3-bedroom, 2-bathroom rental sleeps 6 and features two remote workspaces, a chef's kitchen with stainless steel appliances, a gas fireplace, a king-size Saatva mattress in the primary suite, a queen-size Casper mattress in the third bedroom, a two-car garage with EV charging, and gated outdoor amenities with a Weber propane barbecue.
Old Mill Magic - Bend, OR
9.6 232 reviews

Old Mill Magic

house, Bend
This vacation home in Bend, Oregon, is nestled in the Southern Crossing district, within easy reach of the Old Mill District and Hayden Homes Amphitheater. It has received excellent ratings for its location, cleanliness, and user experience.
The house has a floor area of 1430 square feet and features two bedrooms. It offers a range of amenities, including a fully equipped kitchen, a private water park and spa tub, barbecue grills, free WiFi, a balcony, a fireplace, and parking. Guests can also enjoy access to a restaurant, fitness center, and spa.
Sixties Sweet Spot | Dogs Stay Free - Bend, OR
9.9 20 reviews

Sixties Sweet Spot | Dogs Stay Free

apartment, Bend
This centrally located apartment in Bend offers a peaceful retreat near Pine Nursery Park.
This dog-friendly rental accommodates two guests and features a semi-private yard, dedicated ski/snowboard storage, and convenient parking.

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.

New! Mt Bachelor Village ~ Views ~ Fireplace ~ Private Hot Tub! - Bend, OR
9.8 36 reviews

New! Mt Bachelor Village ~ Views ~ Fireplace ~ Private Hot Tub!

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.

Hollinshead - Orchard District, Amazing Yard! - Bend, OR
10 2 reviews

Hollinshead - Orchard District, Amazing Yard!

apartment, Bend
The Drake Club, Walk To Downtown Ev Charger - Bend, OR
9.6 682 reviews

The Drake Club, Walk To Downtown Ev Charger

cabin, Bend
Hike, Bike & Ski: All-season Bend Escape - Bend, OR
No reviews

Hike, Bike & Ski: All-season Bend Escape

house, Bend
195 M² House ∙ 3 Bedrooms ∙ 8 Guests - Bend, OR
10 2 reviews

195 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, 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.

Wilderness Exploration | 2 Queens + Ada Rated - Bend, OR
8.6 8 reviews

Wilderness Exploration | 2 Queens + Ada Rated

apartment, Bend
Villa #5 At Broken Top - Bend, OR
9.5 209 reviews

Villa #5 At Broken Top

house, Bend
214 M² House ∙ 3 Bedrooms ∙ 8 Guests - Bend, OR
10 1 review

214 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Bend
Downtown Riverfront! Condo Best Location In Bend! - Bend, OR
9.3 92 reviews

Downtown Riverfront! Condo Best Location In Bend!

apartment, Bend
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