Holiday Rentals in Bend, OR

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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 2397 accommodations in Bend, OR, here are the 4 best family friendly rentals

Lodge Vibes In The City - Large Log Home - Bend, OR
10 44 reviews
Bend, OR
10/07 – 17/07
SG$809/nighttotal: SG$5663 (7 )

Lodge Vibes In The City - Large Log Home

3 3
apartment , Bend
This three-bedroom house is situated in Mountain View, Bend, just 3.2 kilometres from Pilot Butte State Park, a popular hiking spot offering scenic views of the city. This spacious property features a fully equipped kitchen, a private garden with barbecue facilities, and a comfortable living area with a fireplace, ideal for families or groups of up to seven guests.
Modern Luxury Base Camp With 3 King Beds 1 Mile To Downtown Bend, 5-star Reviews - Bend, OR
10 76 reviews
Bend, OR
09/08 – 15/08
SG$1079/nighttotal: SG$6474 (6 )

Modern Luxury Base Camp With 3 King Beds 1 Mile To Downtown Bend, 5-star Reviews

3 7
apartment , Bend
This Awbrey Butte holiday home is situated a short 2.4km walk from River’s Edge Golf Course and the Deschutes River, and within 3.2km of the Bend River Promenade.
Sleeping up to seven guests in three bedrooms, this property boasts a fully equipped kitchen, free Wi-Fi, a fireplace, a terrace, parking, and is pet-friendly.
Gateway To Mt Bachelor - Bend, OR
9.8 170 reviews
Bend, OR
17/09 – 19/09
SG$434/nighttotal: SG$868 (2 )

Gateway To Mt Bachelor

2 2
house , Bend
This holiday home is situated in Bend, just 3.8 kilometres from Drake Park and 7.4 kilometres from Hollinshead Park, offering easy access to outdoor activities and scenic views. The property enjoys excellent ratings for location, cleanliness, and user experience.
The 79 square metre property comfortably accommodates up to six guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, a swimming pool, a jacuzzi, free Wi-Fi, and private parking, perfect for a relaxing stay in Bend.
Baltimore Bungalow  Hot Tub, Walkable, Pet-friendly - Bend, OR
10 10 reviews
Bend, OR
09/08 – 15/08
SG$948/nighttotal: SG$5688 (6 )

Baltimore Bungalow Hot Tub, Walkable, Pet-friendly

3 7
apartment , Bend
This Bend holiday home enjoys a riverfront location near the Deschutes River, less than 1.6km from the Old Mill District and a 15-minute drive from Drake Park and Bend Whitewater Park.
The 143 square metre property offers three bedrooms, two bathrooms, sleeps eight guests, and boasts a private patio, swimming pool, jacuzzi, and free Wi-Fi, alongside access to on-site water park facilities.

Best Bend, OR holiday rentals with a fireplace

51 M² Condo ∙ 1 Bedroom ∙ 2 Guests - Bend, OR
9.2 5 reviews
Bend, OR
03/07 – 05/07
SG$395/nighttotal: SG$790 (2 )

51 M² Condo ∙ 1 Bedroom ∙ 2 Guests

1 2
apartment , Bend
This ground-floor apartment in Mount Bachelor Village Resort, Bend, Oregon, offers easy access to the Old Mill District (minutes away) and Mount Bachelor ski resort (under 30 minutes' drive, approximately 24km).
The 51-square-metre (550 sq ft) self-catering property features a bedroom, bathroom, fully equipped kitchen, private balcony overlooking Ponderosa pines, and access to resort amenities including a swimming pool, hot tub, and kids' club, sleeping up to two guests.
Spacious Bend Mid-century•near Old Mill & Downtown - Bend, OR
9.9 255 reviews
Bend, OR
02/07 – 03/07
SG$667/nightfor 1 night

Spacious Bend Mid-century•near Old Mill & Downtown

1 4
apartment , Bend
This Bend property, a four-bedroom mill house situated in a quiet neighbourhood, is minutes from the Old Mill District and the Deschutes River, offering easy access to hiking and biking trails.
Sleeping up to ten guests, the self-catering house boasts a gourmet kitchen, game room with shuffleboard and foosball, a fully enclosed courtyard with BBQ and fire pit, secure bike storage and free Wi-Fi, making it ideal for families or groups.
Aspen @ The Dupe - Blocks From Old Mill District - - Bend, OR
9.9 320 reviews
Bend, OR
08/11 – 10/11
SG$241/nighttotal: SG$482 (2 )

Aspen @ The Dupe - Blocks From Old Mill District -

1 2
house , Bend
This Bend townhouse, located in a quiet cul-de-sac less than 1.1 kilometres from the Old Mill District, offers easy access to shopping, dining, and the Deschutes River.
The two-bedroom, two-bathroom property sleeps up to six guests, includes a modern kitchen with appliances, a dedicated garage, and a small desk in the second bedroom; enjoy the tranquility of this private end-unit duplex.
Ground-floor Condo Near Pioneer Park And Downtown! - Bend, OR
9.0 22 reviews
Bend, OR
03/07 – 05/07
SG$442/nighttotal: SG$884 (2 )

Ground-floor Condo Near Pioneer Park And Downtown!

1 2
apartment , Bend
This one-bedroom flat in Bend's River West district offers easy access to downtown, being an 8-minute walk away, and is only 200 metres from the Deschutes River and its riverside trail.
This 60-square-metre apartment, suitable for two guests, features air conditioning, a kitchen with a fridge, microwave, and dishwasher, two bathrooms, and two private patios, one with a grill, all accessible at ground level.

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.

Destinations nearby

Best Bend, OR holiday rentals with jacuzzi

Ski House 235 - Bend Comfy Condo - Bend, OR
8.5 2 reviews
Bend, OR
22/06 – 24/06
SG$330/nighttotal: SG$660 (2 )

Ski House 235 - Bend Comfy Condo

2 4
house , Bend
Bend Comfy Condo Ski House 235 is situated in Bend, Oregon, 3.7km from Drake Park, 7.2km from Hollinshead Park, and 5.6km from Ponderosa Park, offering convenient access to Bend's popular parks and attractions.
This 84 square metre property features two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, microwave and fridge, plus a swimming pool, jacuzzi, terrace, garden, tennis court, free parking, and free Wi-Fi; ideal for up to four guests seeking a comfortable Bend getaway.
Riverwoods A-frame - Bend, OR
9.9 80 reviews
Bend, OR
23/08 – 24/08
SG$600/nightfor 1 night

Riverwoods A-frame

1 3
cabin , Deschutes River Woods
This three-bedroom A-frame lodge is situated approximately 24 kilometres from Bend city centre, in the Deschutes River Woods, offering easy access to the city's shops and restaurants.
The self-catering property sleeps six guests and boasts a Jacuzzi, garden, free parking, two kayaks, and a Traeger grill, alongside a fully equipped kitchen including fridge, freezer and microwave.
Big Pine Home On Deschutes River Trail - Bend, OR
9.7 173 reviews
Bend, OR
27/09 – 30/09
SG$413/nighttotal: SG$1239 (3 )

Big Pine Home On Deschutes River Trail

3 6
house , Bend
This charming house is situated on the Deschutes River Trail in Bend, just a short drive from Drake Park and Hollinshead Park, offering easy access to the city's attractions and outdoor activities. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property boasts three bedrooms, spanning 195 square metres, making it an ideal choice for families or groups of friends. Guests can enjoy a range of amenities, including a private heated pool, a jacuzzi, a terrace, a garden, a spa, a fitness centre, and free parking, ensuring a comfortable and enjoyable stay.
Tetherow Hotel - Bend, OR
9.2 815 reviews
Bend, OR
02/07 – 03/07
SG$524/nightfor 1 night

Tetherow Hotel

1 4
resort , Tetherow
Tetherow Hotel is located near Deschutes National Forest, a short drive from Bend's city centre and the Old Mill District, offering easy access to both nature and urban amenities. The hotel has consistently received excellent ratings for its location, cleanliness, and overall experience.
The hotel offers spacious and modern rooms with comfortable furnishings and convenient amenities. Guests can enjoy a range of activities including swimming, dining, fitness, and spa treatments, as well as access to a golf course and shuttle service to the city centre.

Best Bend, OR holiday rentals with parking

Gorgeous Retreat, Hot Tub, A/c, Views, Ponds, Ping Pong, Bbq! - Bend, OR
10 3 reviews
Bend, OR
10/07 – 12/07
SG$2021/nighttotal: SG$4042 (2 )

Gorgeous Retreat, Hot Tub, A/c, Views, Ponds, Ping Pong, Bbq!

4 2
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.
Woodhaven House- 1-acre Bend Oasis, Hot Tub, W/office Studio, Pet-friendly - Bend, OR
10 3 reviews
Bend, OR
17/07 – 19/07
SG$1048/nighttotal: SG$2096 (2 )

Woodhaven House- 1-acre Bend Oasis, Hot Tub, W/office Studio, Pet-friendly

2 6
studio , Deschutes River Woods
This detached property is located in Deschutes River Woods, a mere 1600 metres from the Old Mill District and 2400 metres from downtown Bend, offering a private wooded setting on a 0.4-hectare lot.
This 98 square metre annex sleeps eight guests across two bedrooms and two bathrooms, featuring air conditioning, a hot tub, a separate studio space, and a fire pit, all within a 5.6 kilometre drive of Mt. Bachelor.
Riverfront Condo With Balcony Near Downtown Bend - Bend, OR
9.2 57 reviews
Bend, OR
17/09 – 19/09
SG$354/nighttotal: SG$708 (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.
Ski House 106 - Meredith Lodging - Bend, OR
9.2 41 reviews
Bend, OR
14/09 – 17/09
SG$205/nighttotal: SG$615 (3 )

Ski House 106 - Meredith Lodging

1 2
house , Bend
Ski House 106 is located in Bend, just a short distance from Drake, Hollinshead, and Ponderosa Parks, offering easy access to outdoor activities and scenic views. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The house is ideal for families or groups of up to four guests, with a comfortable layout and one bathroom. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, and free parking, ensuring a relaxing and enjoyable stay.
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