New! Diamond Retreat Peaceful Bend Hideaway Near Old Mill & Trails
2 2
apartment , Bend
This three-bedroom flat in Southwest Bend is situated in a quiet residential area, 7 minutes by car from the Old Mill District and 12 minutes from downtown Bend's breweries. This 123 square metre accommodation for six guests offers air conditioning, a fully equipped kitchen, a gas fireplace, and a private back deck, with internet and parking provided.
9.8 114 reviews
Bend, OR
03/07 – 05/07
239 €/nighttotal: 478 € (2 )
Bluebird Day - Ogden Getaway
1 2
apartment , Bend
This Westside Bend studio apartment is located a short walk from Newport Market, Spork, Backporch Coffee, and Chow, and within easy reach of Drake Park and Bend's city centre. The self-catering unit offers a queen-size bed, a fully equipped kitchenette with Caesarstone countertops and stainless steel appliances, a spa shower, and outside storage; it sleeps two guests and includes complimentary tea, coffee, and basic cooking supplies.
10 8 reviews
Bend, OR
09/07 – 12/07
799 €/nighttotal: 2397 € (3 )
New! Brand New Furniture~close To Trails~fireplace
1 6
apartment , Bend
This three-bedroom Bend holiday home is located in the River Wild community of Mount Bachelor Village, offering convenient access to Mount Bachelor ski resort (distance unspecified). Sleeping eight guests, the property boasts a spacious layout with XL king-size beds and bunk beds, a fully equipped kitchen, a two-car garage, and access to River Wild Lodge amenities including a swimming pool and hot tub; a 10% discount applies to bookings of a week or more (excluding Christmas/New Year).
10 1 review
Bend, OR
28/06 – 07/09
300 €/nighttotal: 21300 € (71 )
Prime Downtown Bend Location * Wifi And Cable
1 1
apartment , Bend
This one-bedroom flat is located in the Firehall Building in Downtown Bend, offering immediate walkability to numerous dining, entertainment, and shopping establishments, with the Oxford Suites and Firehouse Restaurant directly across the street and downstairs respectively. This second-floor corner unit sleeps two guests and features a well-equipped kitchen, air conditioning, and complimentary Wi-Fi, with a secured single-car garage space and a barbecue deck available on-site.
9.6 445 reviews
Bend, OR
06/08 – 09/08
216 €/nighttotal: 648 € (3 )
Downtown Den
1 2
apartment , Bend
This dog-friendly apartment is located in Bend's Historic District, just 0.4 kilometres from the city centre and 0.5 kilometres from the Old Mill District, offering easy access to shops, restaurants and entertainment. The apartment has received excellent ratings for cleanliness, location and overall satisfaction. The apartment features an open plan layout and can accommodate up to four guests. It comes equipped with a well-equipped kitchen, high-speed internet, air conditioning and private parking, ensuring a comfortable and convenient stay.
10 117 reviews
Bend, OR
14/09 – 17/09
173 €/nighttotal: 519 € (3 )
Craftsman Style Retreat In Bend River West
1 2
apartment , Bend
This newly completed studio flat is situated in a walkable Bend neighbourhood, a short distance (less than 1.6km) from Columbia Park and within easy walking distance of other parks and the Old Mill District. The self-contained unit, sleeping two, features a kitchen with fridge and freezer, air conditioning, Apple TV, and unique reclaimed woodwork details from a historic Westside home; nearby attractions include Phil's Trails and Mount Bachelor's Park and Ride.
10 4 reviews
Bend, OR
17/07 – 19/07
1308 €/nighttotal: 2616 € (2 )
New Listing! Hot Tub ~ 2 Living Areas ~ Pet Friendly
4 6
apartment , Bend
Brightenwood Retreat, a four-bedroom house in Southeast Bend, offers convenient access to attractions such as the Hayden Homes Amphitheatre and High Desert Museum, though precise distances are unspecified. This self-catering property sleeps eight guests across its spacious layout, boasting a fully equipped kitchen, two living areas with a fireplace and large flat-screen TV, a private hot tub, and BBQ facilities, ideal for exploring Bend's hiking, biking, and winter sports opportunities.
10 213 reviews
Bend, OR
17/07 – 18/07
857 €/nightfor 1 night
Historic Craftsman Bungalow, Just Steps To Downtown ~Hot Tub!~
2 2
apartment , Bend
This Bend holiday home is situated near the Deschutes River, a short 2.4km walk from the Des Chutes Historical Museum and the Old Mill District. The 137 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, and on-site water park.
10 12 reviews
Bend, OR
17/09 – 18/09
330 €/nightfor 1 night
Bluebird Day - Huckleberry Cottage In Bend, Or, Perfect For A Romantic Getaway.
1 2
apartment , Bend
The Huckleberry Cottage is a pet-friendly holiday home in Old Bend, Oregon, a short walk from the Old Mill District and Boneyard Brewing's tasting room. This 40 square metre (approximately 430 square feet) one-bedroom property sleeps four, boasting a fully equipped gourmet kitchen, a spa, and a smart TV, with the option of booking adjacent properties for larger groups.
Bend, OR
03/07 – 05/07
169 €/nighttotal: 338 € (2 )
Sixties Sweet Spot
1 2
apartment , Bend
This centrally located flat is a short distance from Pine Nursery Park, offering a peaceful escape. This dog-friendly studio apartment accommodates two guests and features air conditioning, internet, and dedicated storage for ski and snowboard gear, with a semi-private garden area.
9.8 256 reviews
Bend, OR
01/07 – 05/07
223 €/nighttotal: 892 € (4 )
A Stone's Throw | Riverside Condo - Top Floor
1 2
apartment , Bend
This Westside Bend apartment, situated a short distance (less than 0.5 km) from downtown Bend and the Deschutes River, offers easy access to Pioneer Park and the Bend River Trail. The top-floor condo sleeps four, features two bathrooms, a fully equipped kitchen with balcony gas grill, high-speed internet, Roku Live TV, and family-friendly amenities including a Pack & Play crib and high chair.
8.0 5 reviews
Bend, OR
10/07 – 12/07
357 €/nighttotal: 714 € (2 )
Superior Queen Suite W/ Surrounding Nature Trails!
1 2
resort , Bend
This Bend apartment, situated in Central Oregon on the Deschutes River, offers direct access to the Deschutes River Trail. The 320 sq ft (30 sq m) self-catering unit sleeps four, featuring two queen beds, a kitchenette, and a 55-inch flat-screen TV, plus access to on-site pools, a hot tub, fitness centre, and CURRENTS Lounge and Restaurant.
Best family friendly Bend, OR holiday rentals
Among the 2397 accommodations in Bend, OR, here are the 4 best family friendly rentals
8.7 28 reviews
Bend, OR
23/06 – 26/06
165 €/nighttotal: 495 € (3 )
56 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Bend
This one-bedroom apartment is situated in Mt. Bachelor Village Resort, just a short drive from Bend city centre and less than 30 kilometres from Mt. Bachelor ski resort. The apartment enjoys an excellent user rating and is a popular choice for travellers seeking a comfortable and convenient base for exploring the area. The apartment offers 55 square metres of space, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, restaurant, and parking, as well as access to a shared lounge, game room, and a kids' club area.
10 6 reviews
Bend, OR
17/09 – 18/09
564 €/nightfor 1 night
Downtown Bend Vacation Cottage
1 2
apartment , Bend
This charming cottage is located just a short walk from the Deschutes River, placing you within easy reach of Bend's bustling downtown area, with its numerous breweries, restaurants and coffee shops. It has consistently received excellent reviews from previous guests. The cottage offers a comfortable and modern living space, suitable for up to four guests. Amenities include a fully equipped kitchen, a private garden with a hot tub, a laundry room, parking and a separate living room with a queen-sized sofa bed.
9.7 453 reviews
Bend, OR
06/08 – 09/08
568 €/nighttotal: 1704 € (3 )
Basalt Bungalow - Near Gourmet Grocer, Shops, Hot Tub
2 2
apartment , Bend
This family-friendly house is situated in the mountains of Bend, just 1.5 kilometres from the Deschutes River, Drake Park, and Westside Church. The property has received excellent ratings for location, cleanliness, and overall experience. This 74 square metre house comfortably sleeps up to six guests in its two bedrooms and one bathroom. The house comes equipped with a range of amenities including a swimming pool, Jacuzzi, garden, spa, fitness centre, and a fully equipped kitchen.
10 324 reviews
Bend, OR
17/09 – 19/09
210 €/nighttotal: 420 € (2 )
Villa75: Perfect Midtown Location W/ Cozy Fire Pit
1 2
apartment , Bend
This one-bedroom flat is conveniently located in Bend's Midtown district, just a short walk from the city's best coffee shops, restaurants, and downtown attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. The flat is suitable for two guests and features a well-equipped kitchen, laundry facilities, a cosy living room with an electric fireplace, and access to streaming services. Guests can enjoy a shared backyard with a fire pit, perfect for relaxing evenings under the Bend sky.
Best Bend, OR holiday rentals with a fireplace
9.2 57 reviews
Bend, OR
18/09 – 20/09
257 €/nighttotal: 514 € (2 )
Riverfront Condo With Balcony Near Downtown Bend
1 2
apartment , Bend
This top-floor condominium, situated in Bend's River West district, offers direct access to the Deschutes River and is within 500 meters of downtown amenities and the Old Mill District. This 59 square meter apartment, accommodating up to four guests, features one king bedroom, a queen Murphy bed, two bathrooms, a full kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, and parking, with pets allowed for an additional fee.
Bend, OR
22/07 – 24/07
259 €/nighttotal: 518 € (2 )
Condo Near Downtown Bend - Top-floor With Riverview
1 2
house , Bend
This top-floor flat in Bend offers river views, a 15-minute walk to Drake Park and is 2.1 kilometres from Hollinshead Park. This 59 square metre apartment accommodates up to seven guests, featuring air conditioning, a fully equipped kitchen with a dishwasher, an indoor pool, and free on-site parking.
10 3 reviews
Bend, OR
17/07 – 19/07
1600 €/nighttotal: 3200 € (2 )
Gorgeous Retreat, Hot Tub, A/c, Views, Ponds, Ping Pong, Bbq!
4 6
apartment , Bend
This Bend holiday home, situated in a secluded rural area near Bend, Oregon, offers easy access to attractions such as The Fun Farm and River's Edge Golf Course, with a short drive to the Old Mill District and Bend River Promenade. This five-bedroom, five-bathroom property sleeps twelve guests and boasts a private hot tub, two-car garage with lift, and ample outdoor space with a garden, tennis court, and BBQ grill, ideal for families or large groups.
Bend, OR
25/07 – 27/07
448 €/nighttotal: 896 € (2 )
River Ridge 316a
1 4
house , Bend
River Ridge 316A, a Bend property, is situated in the River Ridge district, approximately 3.9km from Drake Park, 5.8km from Ponderosa Park, and 7.4km from Hollinshead Park. This 81-square-metre house boasts one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, a fireplace, private parking, and an EV charging station.
Frequently asked questions about holiday rentals in Bend, OR
What are the top family-friendly attractions in Bend, OR?
The High Desert Museum is a hit with kids, showcasing the region's wildlife and history. The Drake Park is also a great option for a picnic, with a playground, a pond, and a carousel.
What are the best Airbnb and holiday rentals in Bend, OR?
When is the best time to book a vacation rental in Bend, OR?
Peak season is summer, so you'll want to book well in advance, especially if you're looking for a specific property. Spring and autumn are also popular times, so it's best to book a few months ahead.
What are the best budget-friendly activities in Bend, OR?
There are plenty of free things to do in Bend. Take a walk along the Deschutes River, visit the Cascade Lakes Scenic Byway, or explore the Lava Lands Visitor Center.
What are the best holiday rentals with a pool in Bend, OR?
What are the best restaurants with local dishes in Bend, OR?
Try Anthony's at the Old Mill for fresh seafood and a beautiful view of the Deschutes River. For a casual meal with local ingredients, The Pine Tavern is a classic choice.
What are the best rentals for families and kids in Bend, OR?
What are the best walking or cycling routes in Bend, OR?
The Deschutes River Trail is a popular choice for walking and cycling, offering scenic views of the river and the surrounding mountains. The Old Mill District Loop is also a great option for a short and easy ride.
What are the best rentals or Airbnbs with a jacuzzi in Bend, OR?
Absolutely! Drake Park is dog-friendly, and many of the breweries have outdoor seating where you can enjoy a pint with your furry friend.
What are the benefits of choosing a vacation rental in Bend, OR?
Vacation rentals often offer more space and privacy than hotels, and they can be a great option for families or groups. They also give you the chance to experience Bend like a local.
What are the top sports attractions and facilities in Bend, OR?
Bend is a great place for outdoor sports. The Bend Whitewater Park offers kayaking and rafting opportunities, and the Mt. Bachelor Ski Resort is a popular destination for skiing and snowboarding in the winter.
Destinations nearby
Best Bend, OR holiday rentals with jacuzzi
9.0 2 reviews
Bend, OR
25/07 – 27/07
435 €/nighttotal: 870 € (2 )
Nature Experience | 1king W/ Riverview + Ada Rated
1 4
apartment , Bend
This Bend apartment, situated in the Boyd Acres neighbourhood, offers direct Deschutes River views and is conveniently located near the Deschutes Brewery and River's Edge Golf Course. The one-bedroom, one-bathroom flat sleeps four guests comfortably, boasting a king-size bed, sofa bed, fireplace, 55" Smart TV, and access to on-site amenities including swimming pools, a spa, and fitness centre.
9.6 86 reviews
Bend, OR
22/07 – 24/07
283 €/nighttotal: 566 € (2 )
Top Floor Riverfront Condo At The Edge Of Downtown
1 2
apartment , Bend
This Bend, Oregon apartment, situated near the Deschutes River Trail, offers easy access to walking and cycling paths. The top-floor condo sleeps up to three adults in two separate sleeping areas, boasting a fully equipped kitchen, two bathrooms, a heated indoor pool and hot tub, on-site laundry, and pet-friendly accommodation (two pets maximum, extra charge applies).
Bend, OR
03/07 – 05/07
196 €/nighttotal: 392 € (2 )
Apartment ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Bend
This Bend studio apartment, situated in Mount Bachelor Village, is a short drive (approximately 6km) from Bend city centre and the Deschutes River. The self-contained unit offers a queen-sized bed, sleeps two guests, and includes access to an on-site swimming pool, hot tub, and spa, plus electric vehicle charging.
10 98 reviews
Bend, OR
25/07 – 27/07
578 €/nighttotal: 1156 € (2 )
A Stone's Throw | Sunshine Daydream-saltwater Tub
1 4
bungalow , Bend
This Bend, Oregon cottage is ideally located in the city centre, a short walk (less than 0.5 km) from McMenamins, the Deschutes Brewery, and the Old Mill District. The fully renovated one-bedroom house sleeps four, boasting a saltwater hot tub, fully enclosed garden with BBQ, two parking spaces, and modern amenities including a dishwasher and air conditioning.
Best Bend, OR holiday rentals with parking
9.4 55 reviews
Bend, OR
18/09 – 20/09
209 €/nighttotal: 418 € (2 )
Elegant Second-floor Condo Near Downtown Bend
1 2
apartment , Bend
This newly remodelled one-bedroom condominium offers an unparalleled location adjacent to the Deschutes River Spillway and Pioneer Park, with downtown Bend's restaurants and boutiques within easy walking distance. This 60 square metre flat, suitable for up to four guests, features a full kitchen integrated into the living room, two balconies, a fireplace, a queen-size sofa bed, and complimentary access to Juniper Fitness facilities, including a gym, sauna, and pool.
9.8 407 reviews
Bend, OR
09/07 – 12/07
747 €/nighttotal: 2241 € (3 )
Vintage Awbrey- Fireplace, Hot Tub, Ac, 100+mbps Wifi, Bikes, Walk Downtown
2 6
cottage , Bend
This charming, vintage-modern home is located in the Westside neighbourhood of Bend, just a short walk from the downtown area and close to the Newport district. It has received excellent ratings for location, cleanliness, and overall user experience. The two-bedroom apartment spans 98 square metres and comfortably accommodates up to six guests. The property offers a range of amenities, including a private garden with a hot tub, a fully equipped kitchen, and a fitness centre, making it perfect for a relaxing and enjoyable stay in Bend.
9.8 131 reviews
Bend, OR
14/09 – 17/09
232 €/nighttotal: 696 € (3 )
Deschutes Nest
1 2
house , Bend
Deschutes Nest, a self-catering property in Bend, Oregon, is conveniently located a short 1.1km walk from Drake Park and within a few kilometres of other parks including Hollinshead and Ponderosa. This 81 square metre house boasts one bedroom, one bathroom, a spacious layout including a living room and fully equipped kitchen, plus a private balcony offering mountain views, free private parking, and access to on-site amenities such as a fitness centre and tennis court.
9.6 25 reviews
Bend, OR
24/07 – 27/07
716 €/nighttotal: 2148 € (3 )
Bluebird Day - Box Factory Bungalow, A Charming 2-bedroom Retreat.
2 3
apartment , Bend
This Box Factory Bungalow is situated in Bend's Box Factory district, a short walk or bike ride from Downtown and the Old Mill District. This restored two-bedroom, one-bathroom flat offers 108 square meters of space for up to six guests, featuring a gas fireplace, a fully equipped kitchen with a dining area for six, and a private hot tub, with numerous hiking and mountain biking trails nearby and Cascade Mountains and Mt Bachelor Ski Resort just 32 kilometers away.