Vacation Rentals in Bend, OR

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Bend, OR vacation rentals
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3745 Vacation rentals and Airbnb 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

Westside "Bud-and- Breakfast" - Bend, OR
9.9 350 reviews

Westside "Bud-and- Breakfast"

apartment, Bend
This two-bedroom flat is located in Bend's Westside district, just above the Tokyo Starfish cannabis dispensary. The area offers easy access to restaurants, shops, and parks and has received excellent ratings for its location, cleanliness, and overall experience.
The flat comfortably sleeps six guests and features a fully equipped kitchen, a private balcony, and free Wi-Fi. Guests can enjoy a complimentary gift card to Tokyo Starfish, allowing them to explore a variety of cannabis products in a comfortable and welcoming environment.
A Stone's Throw | Middle Sister - Very Walkable - Bend, OR
9.9 128 reviews

A Stone's Throw | Middle Sister - Very Walkable

bungalow, Bend
This Bend craftsman cottage is ideally located in the downtown residential area, less than 0.16km from Jackson's Corner, 0.48km from the Deschutes River, and 0.64km from Bend's city centre.
The single-bedroom, single-bathroom property sleeps two guests and boasts a fully equipped galley kitchen with Smeg fridge, a European-style washer-dryer, 600 Mbps Wi-Fi, a 50-inch smart TV, and a private backyard with a shared gas grill; plus original fir floors and modern appliances.
Walkers Paradise!
Downtown/river 
Vibes Galore - Bend, OR
10 65 reviews

Walkers Paradise! Downtown/river Vibes Galore

house, Bend
This Bend apartment, situated in the Galveston Corridor, offers easy walking access to Drake Park, Bend city centre, and the Hayden Homes Amphitheatre.
The first-floor flat features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, washer/dryer, two smart TVs, and a deck with fire pit; nearby activities include a scenic 4km walk along the Deschutes River to the Old Mill District.
Cozy Retreat With Gas Fireplace And Access To Pool - Elegant Haven - Bend, OR
No reviews

Cozy Retreat With Gas Fireplace And Access To Pool - Elegant Haven

apartment, Bend
This one-bedroom flat is located within Mt. Bachelor Village Resort, offering easy access to downtown Bend's shops and restaurants, and is under 48 kilometres from Mt. Bachelor ski resort.
This updated 51-square-metre condo sleeps two guests and features a private balcony, a fully equipped kitchen, an in-unit washer/dryer, and access to shared resort amenities including hot tubs and a seasonal swimming pool.

Best Bend, OR holiday rentals with a fireplace

Hideaway Chalet - Bend, OR
9.8 18 reviews

Hideaway Chalet

apartment, Bend
This Bend chalet is conveniently located near downtown Bend, at the foot of Awbrey Butte, and less than a kilometre uphill from the Deschutes River, offering easy access to hiking trails, water activities, and the city centre.
The self-contained cottage features a queen-size bed, ensuite shower room, and a fully equipped kitchen, sleeping up to two guests and providing parking; a playground and large park are within walking distance.
Midtown Bend Getaway - Pet Friendly - Bend, OR
9.5 27 reviews

Midtown Bend Getaway - Pet Friendly

apartment, Bend
This Bend, Oregon apartment is conveniently located near Pilot Butte State Scenic Viewpoint, offering easy access to hiking trails and other Bend attractions within a short driving distance.
Sleeping eight guests, this three-bedroom property boasts a spacious layout including a den, a fully equipped kitchen, two bathrooms, a private patio, and a fully fenced yard with a dog crate – perfect for family getaways near the Deschutes River.
Big Canyon - Community Hot Tub, Seasonal Pool - Bend, OR
9.7 171 reviews

Big Canyon - Community Hot Tub, Seasonal Pool

apartment, Bend
This charming house is situated in Bend, close to the Big Canyon area, just a short drive from Drake Park and Hollinshead Park. It has consistently received excellent user ratings for location, cleanliness, and overall experience.
The property is spacious, offering 236 square metres of living space with four bedrooms. Guests can enjoy a range of amenities, including a heated swimming pool, a jacuzzi, a private patio, and a fully equipped kitchen, making it ideal for families or groups of friends seeking a comfortable and convenient stay in Bend.
Bend Condo Near Mt Bachelor With Hot Tub Sleeps 6 - Bend, OR
9.0 12 reviews

Bend Condo Near Mt Bachelor With Hot Tub Sleeps 6

apartment, Bend
This Bend apartment, located in Mount Bachelor Village Resort, is a short drive (a few kilometres) from downtown Bend, the Old Mill District, and Mount Bachelor Ski Resort, offering easy access to numerous attractions.
The one-bedroom condo boasts a spacious open-plan layout, sleeping up to six guests and featuring a well-equipped kitchen, balcony with mountain views, and resort amenities including a swimming pool, Jacuzzi, and access to a nature trail.

Frequently asked questions about holiday 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 and there are some lovely shops and restaurants there. If you're into craft beer, you can't miss the Deschutes Brewery, it's a Bend institution. And if you're looking for something a bit more adventurous, head up to Pilot Butte State Scenic Viewpoint for incredible views of the city and the surrounding mountains.
  • What are the best Airbnb and vacation rentals in Bend, OR?

    Private Apartment - Your Bend Escape - Right In Town, Kathy's Westside Compound 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, it's close to the Deschutes River and has easy access to shops, restaurants, and activities. If you're looking for something a bit quieter, the Westside is a great option, it's known for its charming streets and proximity to the Cascade Lakes.
  • 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, it's a great place to learn about the region's natural history and see some amazing animals. The Discovery Center at the River is another great option, it's a hands-on science museum with lots of interactive exhibits. And if you're looking for something a bit more active, the Pilot Butte State Scenic Viewpoint offers stunning views and a great hiking trail.
  • 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?

    The best time to book a vacation rental in Bend is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and the prices will be more reasonable. If you're looking for snow sports, then you'll want to book during the winter months, from December to March.
  • What are the best rentals for families and kids in Bend, OR?

  • What events or festivals should visitors check out in and around Bend, OR?

    The Bend Brewfest is a popular event, it's held every August and features over 50 breweries from around the region. The Bend Film Festival is another great option, it's held every October and showcases independent films. And if you're visiting during the summer, you can check out the Bend Summer Concert Series, which features free concerts every week at the Les Schwab Amphitheater.
  • What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?

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

    You can explore the many free walking trails in the area, like the Deschutes River Trail or the Old Mill District Trail. The Drake Park is a great place to have a picnic and enjoy the scenery, and you can also visit the free exhibits at the High Desert Museum.
  • What are the best restaurants with local dishes in Bend, OR?

    Try the Bend Brewing Company, it's a great place to sample local craft beers and enjoy some delicious pub grub. The Pine Tavern is another popular choice, it's a historic restaurant serving up classic American dishes. And if you're looking for something a bit more upscale, the 900 Wall is a great option, it's known for its farm-to-table cuisine.
  • What are the best walking or cycling routes in Bend, OR?

    The Deschutes River Trail is a great option for both walking and cycling, it runs along the river and offers stunning views of the Cascade Mountains. The Old Mill District Trail is another good choice, it's a paved path that runs through the heart of the Old Mill District. And if you're looking for a more challenging ride, you can check out the Cascade Lakes Scenic Byway, which offers incredible views of the lakes and mountains.
  • Are there pet-friendly attractions in Bend, OR?

    Yes, many of the parks and trails in Bend are pet-friendly. The Drake Park is a great place to let your dog run around, and the Deschutes River Trail is also pet-friendly. You can also check out the dog-friendly patios at many of the restaurants and breweries in town.
  • What are the benefits of choosing a vacation rental in Bend, OR?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens 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 popular destination for outdoor sports enthusiasts. The area has over 300 km of mountain biking trails, and there are plenty of opportunities for hiking, rock climbing, and kayaking. The city also has a number of golf courses and a ski resort, Mt. Bachelor, located just a short drive away.

Popular destinations

Best Bend, OR holiday rentals with jacuzzi

Studio Flat ∙ 1 Bedroom ∙ 4 Guests - Bend, OR
No reviews

Studio Flat ∙ 1 Bedroom ∙ 4 Guests

studio, Bend
This Bend studio apartment, situated directly on the Deschutes River with immediate access to the Deschutes River Trail, offers convenient proximity to Bend's attractions.
The 30-square-metre suite features two queen-size beds sleeping up to four guests, a private balcony, a 55-inch flat-screen TV with HBO, and access to Riverhouse Lodge amenities including pools, a hot tub, and a fitness centre.
Patio & Pool Access! Year-round Base In Bend - Bend, OR
9.2 5 reviews

Patio & Pool Access! Year-round Base In Bend

house, Bend
This two-bedroom apartment is located in Mt Bachelor Village Resort, just 30 kilometres from Mt. Bachelor Ski Resort, 3.7 kilometres from Drake Park and 7.2 kilometres from Hollinshead Park in Bend. The surrounding area offers a range of outdoor activities and attractions, making it an ideal base for exploring the region.
The 78 square metre apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a balcony and a garden. It also offers a range of amenities, including a swimming pool, a jacuzzi, a spa, parking, and free Wi-Fi.
Ponderosa Vista - Resort Condo - Bend, OR
9.0 1 review

Ponderosa Vista - Resort Condo

house, Bend
This Ponderosa Vista Resort condo is situated in Bend, Oregon, 4 kilometres from Drake Park and 7.2 kilometres from Hollinshead Park, offering convenient access to Bend's parks and outdoor recreation.
The 78-square-metre property features one bedroom, one bathroom, and accommodates up to seven guests, boasting a fully equipped kitchen, swimming pool, jacuzzi, and free Wi-Fi.
Pet Friendly Cottage On The River Near Downtown! - Bend, OR
9.4 35 reviews

Pet Friendly Cottage On The River Near Downtown!

apartment, Bend
This studio cottage is located in Bend's River West neighbourhood, offering direct access to the Deschutes River and a 10-minute walk to the town centre.
This 41 square metre studio sleeps two guests, featuring a kitchenette, king-sized bed, electric fireplace, air conditioning, and access to an indoor heated pool and hot tub, with pets welcome for an additional fee.

Best Bend, OR holiday rentals with parking

Downtown With Hot Tub And Fenced-in Yard - Bend, OR
9.9 169 reviews

Downtown With Hot Tub And Fenced-in Yard

apartment, Bend
This Bend downtown cottage offers a pet-friendly one-bedroom apartment, within walking distance of the Deschutes River Trail and numerous breweries, restaurants, and art galleries.
The property features a private landscaped yard with a hot tub, a complete remodel with new appliances, an open-plan layout with vaulted ceilings, and accommodates up to four guests with a queen-size bed and a hide-a-bed sofa.
New! Historic Bend Cottage | Walk To Breweries & Drake Park - Bend, OR
8.8 11 reviews

New! Historic Bend Cottage | Walk To Breweries & Drake Park

apartment, Bend
This 68 square metre flat, located in Bend's River West district, offers a historic 1930s cottage experience with a modern renovation, situated a mere 2-block walk from downtown shops, breweries, restaurants, and Drake Park, with Phil's Trailhead accessible by bike and Mt. Bachelor and Smith Rock State Park a 30-35 minute drive away.
This pet-friendly accommodation for up to six guests features two bedrooms, one bathroom, whole-house air conditioning, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, and a dedicated workspace, making it ideal for remote workers seeking a prime downtown Bend location.
The Birdseye House - Bend, OR
9.8 425 reviews

The Birdseye House

apartment, Bend
This two-bedroom apartment is situated in Bend, a short distance from breweries, ski resorts, shopping, the city centre, and the Old Mill District, offering easy access to Bend's attractions. The apartment has received excellent ratings for user experience, location, and cleanliness.
The property features a spacious and open plan layout, perfect for groups of up to four guests. Enjoy convenient amenities like free Wi-Fi, air conditioning, and bikes, as well as a fully equipped kitchen, a private garden, and a fitness centre.
Connect With Nature | 1 King + Ada Rated - Bend, OR
8.8 5 reviews

Connect With Nature | 1 King + Ada Rated

apartment, Bend
This pet-friendly apartment, situated in Bend's Boyd Acres neighbourhood, offers easy access to the Deschutes River Trail and is within close proximity (exact distances unspecified) of the River's Edge Golf Course and Bend River Promenade.
The self-catering unit features a king-size bed, a 200–300 sq ft space, a private patio, and access to on-site amenities including pools, a hot tub, and fitness centre; accommodating up to two guests.
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