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

River Village 331ab Ground Floor Condo In Bend, Or 2 Bd, 2 Ba - Bend, OR
10 1 review

River Village 331ab Ground Floor Condo In Bend, Or 2 Bd, 2 Ba

apartment, Bend
This 2-bedroom, 2-bathroom condo in Bend's Century West neighborhood offers direct access to the Deschutes River Trail and is located minutes from the Old Mill District, Downtown Bend, and Mt. Bachelor, which is 19 miles away.
This family-friendly apartment accommodates up to 6 guests and features a seasonal swimming pool, year-round hot tub, playground, game room, and a private deck with river views, along with an open-concept living space with a gas fireplace and Smart TV.
Fall Creek Suite - Awesome Westside Location - Bend, OR
9.5 455 reviews

Fall Creek Suite - Awesome Westside Location

apartment, Bend
The Fall Creek suite, a two-bedroom rental in Northwest Bend, offers easy access to restaurants and shops, and is conveniently located near outdoor recreation areas such as Mount Bachelor and Smith Rock State Park.
This single-level vacation home sleeps four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, a private patio with a BBQ, secure garage parking, and air conditioning.
Upper-level Condo With Mt. Bachelor Village Amenities! - Bend, OR
10 1 review

Upper-level Condo With Mt. Bachelor Village Amenities!

apartment, Bend
This condo in Bend's Century West neighborhood is located within Mt. Bachelor Village Resort, offering direct access to the Deschutes River Trail and a 10-15 minute drive to Mt. Bachelor Ski Resort and downtown Bend.
This 900 sq ft residence accommodates up to 5 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, gas fireplace, private loft workspace, and access to seasonal resort amenities including a swimming pool and hot tubs.
Studio Flat ∙ 1 Bedroom ∙ 2 Guests - Bend, OR
No reviews

Studio Flat ∙ 1 Bedroom ∙ 2 Guests

studio, Bend
This Bend, Oregon studio apartment is conveniently located near the Deschutes River and the Deschutes River Trail, offering easy access to outdoor recreation and the River's Edge Golf Course.
This family-friendly unit boasts 200-300 square feet of space, featuring a king bed, a workspace, a private balcony or patio, and access to on-site amenities including heated pools, hot tubs, and a fitness center; it comfortably sleeps two guests.

Best Bend, OR vacation rentals with a fireplace

Third-floor Riverfront Condo Near Downtown Bend - Bend, OR
9.0 12 reviews

Third-floor Riverfront Condo Near Downtown Bend

apartment, Bend
This one-bedroom condo is located in the River West neighborhood of Bend, offering a prime riverside setting with direct walking access to downtown amenities and attractions, and is situated within a short distance of River's Edge Golf Course and Deschutes Brewery. This 640 sq ft unit accommodates up to two guests, featuring a queen bed, two bathrooms, a remodeled kitchen with a fridge, microwave, and dishwasher, air conditioning, a gas fireplace, and access to an indoor heated pool and hot tub.
Cozy 3-bedroom W/ Fireplace & Office Near Old Mill - Bend, OR
9.7 69 reviews

Cozy 3-bedroom W/ Fireplace & Office Near Old Mill

apartment, Bend
This Bend, Oregon mill is conveniently located near the Old Mill District (5-minute drive), Deschutes River Trail (8-minute drive), and Farewell Park (9-minute drive), with Mt. Bachelor a 30-minute drive away.
This family-friendly vacation home sleeps eight guests in three bedrooms and two bathrooms, boasting a kitchen with modern appliances, a fireplace, outdoor fire pit and grill, garage storage for water toys, and USB charging lights in each bedroom.
Walk To Downtown, Trails, And The River! - Bend, OR
9.6 83 reviews

Walk To Downtown, Trails, And The River!

apartment, Bend
This Bend condo, a three-minute walk from the Deschutes River and ten minutes from downtown, offers easy access to the Deschutes River Trail, Pioneer Park, and Highways 20 and 97.
The one-bedroom, two-bathroom unit sleeps four, features two balconies overlooking Pioneer Park, a full kitchen with dishwasher, a king-size bed, a fireplace, air conditioning, a Roku entertainment system, and private parking.
Villa75: Perfect Midtown Location W/ Cozy Fire Pit - Bend, OR
10 338 reviews

Villa75: Perfect Midtown Location W/ Cozy Fire Pit

apartment, Bend
This stylish one-bedroom apartment is located in Bend's Midtown district, just a short walk from the city's best coffee shops, restaurants, and downtown attractions. It has received excellent ratings for location, cleanliness, and user experience.
The apartment comfortably accommodates two guests and features a well-equipped kitchen, a cozy sitting area, a fireplace, and a washer and dryer. Enjoy evenings by the shared fire pit, access to streaming services, and freshly ground local coffee.

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.

New! Cozy Condo | Hot Tub - Pool | Steps To River Trail - Bend, OR
9.4 22 reviews

New! Cozy Condo | Hot Tub - Pool | Steps To River Trail

apartment, Bend
This condo is located in Bend's Century West neighborhood, offering direct access to the Deschutes River Trail and a short drive to Mt. Bachelor and downtown Bend.
This 620 sq ft, 2-bedroom, 1-bathroom condo accommodates up to 4 guests and features a newly remodeled interior, a private BBQ patio, and access to community amenities including a seasonal swimming pool and year-round hot tub.
Frosty Summit Condo, Mount Bachelor W/ Pool - Bend, OR
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 from downtown Bend and Mount Bachelor.
The one-bedroom, one-bathroom unit sleeps two guests and features a full kitchen, private balcony, access to a shared pool and hot tub, and a streaming-enabled TV.
Second-floor - Riverfront Condo Near Downtown Bend - Bend, OR
9.0 2 reviews

Second-floor - Riverfront Condo Near Downtown Bend

house, Bend
This riverfront condo in Bend is a 15-minute walk from Drake Park and 1.3 miles from Hollinshead Park.
This 640 square foot condo accommodates up to 7 guests and features an indoor swimming pool, a fully equipped kitchen with a dishwasher, and complimentary on-site parking and free WiFi.
Spacious Two Story 2 Bed 2 Bath West Side Condo - Bend, OR
9.8 161 reviews

Spacious Two Story 2 Bed 2 Bath West Side Condo

house, Bend
This family-friendly condo is located in Century West, just a short distance from the Deschutes River, Old Mill District, and Hayden Homes Amphitheater. The condo has received excellent ratings for user experience, location, and cleanliness.
The 1420 square foot condo has 2 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy amenities like a private patio with barbecue grills, a spa tub, a fireplace, and a fully equipped kitchen.

Best Bend, OR vacation rentals with parking

Cabin On Quiet 3 Acres 10 Min To Downtown Bend. - Bend, OR
9.9 337 reviews

Cabin On Quiet 3 Acres 10 Min To Downtown Bend.

house, Bend
This peaceful guest house is located in a quiet neighborhood just 10 minutes from downtown Bend, making it a convenient base for exploring the city and nearby attractions like Mt. Bachelor, Smith Rock, and Phil's trailhead. This property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cozy dwelling comfortably sleeps up to 4 guests with a king bed, two twin beds, and a queen-size sofa bed. Guests can enjoy the peaceful surroundings with a large lawn, an irrigation pond, a fire pit, and access to a nearby park with trails, pickleball courts, and a playground.
Ski House 217 - Bend, OR
9.2 21 reviews

Ski House 217

house, Bend
Ski House 217 is located in Bend, just a short drive from Drake Park and Hollinshead Park, making it a great base for exploring the city and its surrounding natural beauty. The house has received excellent ratings for its cleanliness, location, and overall experience.
The 2-bedroom house, with a capacity of 4 guests, offers 840 square feet of comfortable living space. Enjoy the fully equipped kitchen, private balcony, and access to amenities like a swimming pool, Jacuzzi, and fitness center.
Downtown Studio On The River - Bend, OR
9.0 102 reviews

Downtown Studio On The River

apartment, Bend
License to Grill, a ground-floor studio apartment in Bend, Oregon, offers riverfront views of the Deschutes River and easy access to its recreational activities.
This one-bedroom unit sleeps up to four guests and features a full kitchen, in-unit laundry, a private patio, and access to a heated indoor pool and hot tub.
Midtown Mecca- Deck, Yard, And Fruit Trees! - Bend, OR
9.8 468 reviews

Midtown Mecca- Deck, Yard, And Fruit Trees!

apartment, Bend
This private room is located just over 2 miles from downtown Bend, offering easy access to the city's attractions while maintaining a peaceful retreat. The accommodation boasts excellent user, location, and cleanliness ratings, ensuring a comfortable stay.
The private room features a separate entrance and a kitchenette with a mini-fridge, microwave, and coffee maker. Enjoy outdoor access with a private deck, hammock, and secure storage for bikes or ski equipment, perfect for exploring Bend's natural beauty.

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.

Ski House 133 - Meredith Lodging - Bend, OR
9.1 90 reviews

Ski House 133 - Meredith Lodging

house, 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.

River View Condo- Edge Of Downtown - Bend, OR
8.4 43 reviews

River View Condo- Edge Of Downtown

apartment, Bend
Bluebird Day - Casa Luna - Bend, OR
9.0 2 reviews

Bluebird Day - Casa Luna

house, Bend
Bluebird Day - Huckleberry Cottage - Bend, OR
10 1 review

Bluebird Day - Huckleberry Cottage

house, Bend
Riverfront Cottage - Steam Room & Pet Friendly! - Bend, OR
9.2 38 reviews

Riverfront Cottage - Steam Room & Pet Friendly!

cottage, 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
2beds - Family-friendly- Mt Bachelor Village - Bend, OR
8.0 1 review

2beds - Family-friendly- Mt Bachelor Village

house, Bend
River View 2 Bedroom - Bend, OR
9.5 56 reviews

River View 2 Bedroom

house, Bend
Newly Updated And Remodeled! Private Hot Tub! Lockable Storage In Garage. - Bend, OR
9.8 36 reviews

Newly Updated And Remodeled! Private Hot Tub! Lockable Storage In Garage.

apartment, Bend
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