Holiday Rentals in Bend, OR

3745 available vacation rental offers

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Bend, OR holiday rentals
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Best Holiday rentals and Airbnb offers in Bend, OR

Best family friendly Bend, OR holiday rentals

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

Private Yard And Peaceful Deck Retreat - Sleek Modern Oasis - Bend, OR
No reviews

Private Yard And Peaceful Deck Retreat - Sleek Modern Oasis

house, Bend
This newly constructed Mod Pod in Bend offers convenient access to downtown attractions, placing you just a short distance from the city's vibrant core.
This family-friendly accommodation sleeps four, featuring one bedroom, one bathroom, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and a private garden with a deck.
Near Old Mill - No Pets - Top 5% - Nordic Sauna - Bend, OR
10 271 reviews

Near Old Mill - No Pets - Top 5% - Nordic Sauna

bungalow, Bend
This Bend bungalow, a completely remodelled 1930s mill house, is located near the Old Mill District, a mere 1.8 km from both the district and Highway 97.
The self-catering cottage offers one bedroom, one bathroom, sleeps four guests comfortably, and features a fully equipped kitchen, cosy living room with fireplace, and a private yard with a propane fire table; construction next door begins July 2024.
Cozy 3-br House W/ Ev Charger & Trailer Parking - Bend, OR
9.6 113 reviews

Cozy 3-br House W/ Ev Charger & Trailer Parking

apartment, Bend
This Bend holiday home, a three-bedroom, two-bathroom caravan, is situated two blocks from Farewell Bend Park, 1.6km from the Old Mill District, and 2.4km from the Hayden Homes Amphitheatre, offering easy access to the Deschutes River and Mt. Bachelor (a 32km drive).
Sleeping six, the property includes a kitchen with a fridge, air conditioning, a garden, parking, laundry facilities, a Level 2 EV charger, smart TVs, a jacuzzi bath, and heated floors in the master suite; a twin trundle bed converts to a king-size, and pets are welcome for a £40 non-refundable fee.
Lodge Vibes In The City With Gym & Sauna - Bend, OR
10 371 reviews

Lodge Vibes In The City With Gym & Sauna

apartment, Bend
This modern log cabin is located in Bend, just a short 10-minute drive from the city centre and the Old Mill District, offering a peaceful retreat in a quiet residential neighbourhood. The cabin has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious three-bedroom, three-bathroom property comfortably accommodates six guests. It features a fully equipped kitchen, a welcoming fireplace, a dedicated office nook, a playroom, and a flex-space above the garage, offering ample room for work, play, and relaxation.

Best Bend, OR holiday rentals with a fireplace

Tommy - Close To Fun! Fireplace, A/c, Fenced Yard - Bend, OR
No reviews

Tommy - Close To Fun! Fireplace, A/c, Fenced Yard

apartment, Bend
This flat in Bend's Larkspur district is situated a short walk from Pettigrew Park and the Deschutes River, and close to Pilot Butte State Park, with convenient access to local eateries, breweries, shops, and Whole Foods Market.
This 175 square metre dwelling offers three bedrooms and three bathrooms to accommodate up to seven guests, featuring a modern, open-plan living space, a cosy fireplace, a fully fenced garden suitable for pets, and is well-placed for outdoor pursuits including skiing at Mount Bachelor, just over 25 kilometres away.
Pool, Ac, Close To Amphitheater & Old Mill - Bend, OR
10 141 reviews

Pool, Ac, Close To Amphitheater & Old Mill

apartment, Bend
This Bend condo is ideally situated near the Deschutes River Trail, less than 1.6km from the Old Mill District shopping and dining area, and a short walk further to the Les Schwab Amphitheatre.
The one-bedroom apartment, sleeping four, boasts a well-equipped kitchen, a comfortable living room with a Murphy bed and gas fireplace, a private patio with forest views, and a bathroom with accessibility features; enjoy nearby hiking, river walks, and summer concerts.
Desert Oasis (Private Acreage) - Bend, OR
10 59 reviews

Desert Oasis (Private Acreage)

gîte, Bend
This private, gated annex in Bend is located 10 minutes from the city centre, providing easy access to restaurants, shops, and outdoor pursuits including Smith Rock and Mt. Bachelor.
This pet-friendly accommodation offers a full kitchen, gas fireplace, private patio with a grill and fire pit, and sleeps up to three guests, with pickleball courts available on request.
Cozy Nw Bachelor Escape Near The River / Hot Tub - Bend, OR
9.1 47 reviews

Cozy Nw Bachelor Escape Near The River / Hot Tub

apartment, Bend
This cosy two-bedroom apartment near Bend, Oregon offers convenient access to the Deschutes River and scenic hiking trails, boasting breathtaking Cascade Mountain views.
The self-catering flat sleeps four, features a fully equipped kitchen, a private backyard deck with a hot tub and gas fireplace, and provides convenient driveway parking; pets are welcome.

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 fantastic restaurants there. The Deschutes Brewery is a must-visit for any beer lover and you can't go wrong with a walk or bike ride along the Deschutes River Trail.
  • What are the best Airbnb and vacation rentals in Bend, OR?

  • Which neighborhood in Bend, OR should you consider for a vacation rental?

    The Old Mill District is a popular choice, but if you're looking for something a bit quieter, the Westside is a good option. It's close to the river and has a more residential feel.
  • 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 great place to learn about the local wildlife and history. The Pilot Butte State Scenic Viewpoint is a must-do for families, offering stunning views of the city and surrounding area. And, of course, there's always the fun of the Drake Park, a great place to let the kids run around.
  • 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 is from June to September, so booking in advance is essential. If you're looking for a more affordable trip, consider visiting during the shoulder seasons (spring and autumn) when the weather is still pleasant.
  • 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 held every summer, and the Bend Film Festival is a great way to experience the local film scene. If you're here in the winter, the Bend Winterfest is a fun event with ice sculptures, live music, and more.
  • What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?

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

    Hiking and biking are great free activities in Bend. The Deschutes River Trail is a great option for both, and there are plenty of other trails to explore. You can also enjoy a picnic at Drake Park or visit the free exhibits at the High Desert Museum.
  • What are the best restaurants with local dishes in Bend, OR?

    For a truly local dining experience, try Anthony's at the Old Mill, known for its delicious seafood. The Pine Tavern is another popular spot, serving up classic American fare with a Bend twist. And for something a bit more casual, try the Cascade Lakes Brewing Company for their award-winning craft beers and tasty pub grub.
  • What are the best walking or cycling routes in Bend, OR?

    The Deschutes River Trail is a great option for both walking and cycling, offering stunning views of the river and surrounding mountains. For a more challenging ride, try the Century Drive loop, a scenic 70km route that takes you through the Cascade Mountains.
  • Are there pet-friendly attractions in Bend, OR?

    Absolutely! Many of the parks in Bend are pet-friendly, including Drake Park and Pilot Butte State Scenic Viewpoint. The Deschutes River Trail is also a great option for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Bend, OR?

    Vacation rentals offer more space and privacy than hotels, and 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 great place for outdoor sports enthusiasts. The area is known for its world-class skiing and snowboarding in the winter, and there are plenty of hiking and biking trails to explore year-round. The Bend Golf Club is a popular option for golfers, and the Deschutes River is a great place for kayaking, paddleboarding, and fishing.

Popular destinations

Best Bend, OR holiday rentals with jacuzzi

Hottub, Near Old Bend & Downtown | Aerie 2bdr King - Bend, OR
9.6 18 reviews

Hottub, Near Old Bend & Downtown | Aerie 2bdr King

apartment, Bend
This modern two-bedroom flat is located in Bend's Discovery West neighbourhood, offering a walkable plaza and being approximately 40 kilometres from Mt Bachelor and 16 kilometres from downtown Bend.
This property accommodates four guests and features a private balcony with a hot tub, a front balcony with an electric barbecue, in-home laundry, and ski/snowboard/bike storage, with EV charging available and access to Discovery Perks discounts.
Treetop View Of A Little Bit Of Heaven. - Bend, OR
9.8 63 reviews

Treetop View Of A Little Bit Of Heaven.

apartment, Deschutes River Woods
This Deschutes River Woods apartment, a one-bedroom condo on the third floor, offers spectacular views of the Deschutes National Forest treeline and is located directly adjacent to the Deschutes River, providing immediate access to various water activities.
The 1-bedroom flat sleeps four guests, featuring a king-size bed, a queen-size Murphy bed, a fully equipped kitchen with granite island, two flat-screen TVs, a patio with mountain views, and access to on-site resort amenities including multiple heated pools, hot tubs, a fitness centre, and more.
Ski House 154 - Meredith Lodging - Bend, OR
9.0 32 reviews

Ski House 154 - Meredith Lodging

house, Bend
This Bend holiday home is conveniently located approximately 4.2km from Drake Park, 7.4km from Hollinshead Park, and 4.8km from Ponderosa Park, offering easy access to outdoor recreation.
This 79 square metre property sleeps four in two bedrooms and two bathrooms, boasting a private balcony, swimming pool, jacuzzi, and well-equipped kitchen including a dishwasher, microwave, and fridge; plus nearby skiing opportunities make this a great base for exploring Bend.
Rustic Cottage With Views Of The Deschutes River - Bend, OR
No reviews

Rustic Cottage With Views Of The Deschutes River

house, Bend
This rustic cottage in Bend is located 1.3 kilometres from Drake Park, 2.1 kilometres from Hollinshead Park, and 4 kilometres from Ponderosa Park, offering city views.
This 30 square metre dwelling accommodates up to three guests and features a kitchen with a fridge and microwave, air conditioning, an indoor swimming pool, a jacuzzi, and parking, with free WiFi and TV provided.

Best Bend, OR holiday rentals with parking

New! Pineview Getaway | Mt. Bachelor Village - Bend, OR
10 2 reviews

New! Pineview Getaway | Mt. Bachelor Village

apartment, Bend
This ground-level condo in Mt. Bachelor Village Resort is located a stone's throw from the Deschutes River Trail, 2.4 kilometres from the Old Mill District, and 3.2 kilometres from downtown Bend.
This one-bedroom flat, accommodating up to four guests, features a well-equipped kitchenette, a gas fireplace, a Smart TV, and offers resort amenities such as a swimming pool and hot tubs, with direct access to the Deschutes River Trail for outdoor pursuits.
Charming Millhouse W/  Hot Tub Close To Everything - Bend, OR
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.
Dogok. Large Retreat, 3 King Beds. Fire Pit - Bend, OR
9.7 213 reviews

Dogok. Large Retreat, 3 King Beds. Fire Pit

apartment, Bend
This spacious home is located on the East Side of Bend, just 5 kilometres from the city centre and within walking distance of shops, restaurants, and cafes. It has received excellent ratings for location, cleanliness, and overall guest experience.
The property offers 209 square metres of living space, accommodating up to 8 guests across three bedrooms. It features a well-equipped kitchen, a relaxing garden with a fire pit, and a comfortable living area with TVs and a desk.
20 Min To Mt Bachelor Perfect Basecamp For Skiers - Bend, OR
No reviews

20 Min To Mt Bachelor Perfect Basecamp For Skiers

apartment, Bend
This Bend apartment offers a convenient base near Ponderosa and Hollinshead Parks, approximately 8 kilometres from each, and a short drive from Drake Park, providing easy access to green spaces and outdoor activities.
The 65 square metre self-catering flat sleeps three, features a kitchenette with microwave and fridge, free Wi-Fi, parking, and air conditioning, and is ideally located for exploring Bend and Mount Bachelor (a 32 km drive).
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