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

Mid Century Luxury Home; Westside; Walk Everywhere - Bend, OR
10 298 reviews
Bend, OR
27/06 – 04/07
SG$757/nighttotal: SG$5299 (7 )

Mid Century Luxury Home; Westside; Walk Everywhere

2 2
apartment , Bend
This mid-century ranch house is situated in West Bend, a short walk from Newport Avenue and its restaurants and coffee shops, and only 0.8 kilometres from Newport Market and 1.6 kilometres from Bend city centre.
The 152 square metre property features two bedrooms, two bathrooms, and can accommodate up to six guests, and includes a well-equipped kitchen, a garden, a spa, and parking, as well as air conditioning and internet access.
New! Cozy Bend Escape | Hot Tub | Forest Views - Bend, OR
Bend, OR
01/07 – 05/07
SG$645/nighttotal: SG$2580 (4 )

New! Cozy Bend Escape | Hot Tub | Forest Views

3 2
apartment , Bend
This upper-level corner condo in Mt. Bachelor Village Resort, Century West, is situated just 3 kilometres from Pilot Butte and Tumalo State Parks, offering proximity to the mountains and river.
This 79 square metre apartment sleeps six and features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a hot tub, and a fireplace, with access to outdoor activities like mountain biking and hiking.
Park Place - Updated W/hot Tub, Yard, Ac - Bend, OR
10 4 reviews
Bend, OR
24/07 – 27/07
SG$806/nighttotal: SG$2418 (3 )

Park Place - Updated W/hot Tub, Yard, Ac

3 3
apartment , Bend
This apartment in scenic Bend, Oregon, offers convenient access to outdoor pursuits, being a short drive to the Deschutes River Trail and world-class skiing at Mt. Bachelor.
This family-friendly property accommodates up to six guests across three bedrooms and features a private hot tub, a furnished deck, a spacious garden, and a cosy pellet stove.
Drake Park Villa Home - Bend, OR
9.7 175 reviews
Bend, OR
24/07 – 27/07
SG$2260/nighttotal: SG$6780 (3 )

Drake Park Villa Home

3 3
house , Bend
Drake Park Villa is a short walk from Drake Park in Bend, offering easy access to other parks and attractions. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The villa provides comfortable accommodation for families or groups with three bedrooms, a living room, and two bathrooms. Guests can enjoy a range of amenities including a swimming pool, spa, fitness centre, and a private patio, as well as free parking and internet access.

Best Bend, OR holiday rentals with a fireplace

New Listing! Mountain Views ~ Dog Friendly ~ Fireplace ~ Fenced Yard! - Bend, OR
Bend, OR
10/07 – 17/07
SG$763/nighttotal: SG$5341 (7 )

New Listing! Mountain Views ~ Dog Friendly ~ Fireplace ~ Fenced Yard!

3 3
apartment , Bend
This dog-friendly flat in Boyd Acres, Bend, offers mountain views and is a short drive to Cascade Village Shopping Centre (approx. 800 metres) and Costco, with Downtown Bend, Sawyer Park, and popular breweries just 10 minutes away.
Spanning 186 square metres, this three-bedroom, three-bathroom residence accommodates six guests and features a fully equipped kitchen with stainless steel appliances, air conditioning, and an expansive back deck perfect for enjoying sunset views.
Downtown Studio On The River - Bend, OR
9.0 95 reviews
Bend, OR
04/07 – 06/07
SG$373/nighttotal: SG$746 (2 )

Downtown Studio On The River

1 3
apartment , Bend
License to Grill is a ground-floor apartment situated near the Deschutes River in Bend, Oregon, offering convenient access to the river's recreational activities.
This self-catering studio sleeps up to four guests and boasts a full kitchen, bathroom, and access to an indoor heated pool and hot tub, along with complimentary coffee.
West Bend Bike And Ski Getaway - Bend, OR
9.0 1 review
Bend, OR
02/07 – 03/07
SG$843/nightfor 1 night

West Bend Bike And Ski Getaway

3 4
house , Bend
West Bend Bike and Ski Getaway is located in Bend, Oregon, approximately 3.5km from Drake Park and 8.2km from Hollinshead Park, offering easy access to popular Bend parks and outdoor recreation.
This 149 square metre, one-bedroom property sleeps eleven guests and boasts a fully equipped kitchen, Jacuzzi, garden, free Wi-Fi, and private parking, plus outdoor play equipment for families.
Bend, Or-seventh Mountain Resort-1bd Dlxe - Bend, OR
Bend, OR
28/06 – 07/09
SG$334/nighttotal: SG$23714 (71 )

Bend, Or-seventh Mountain Resort-1bd Dlxe

1 1
apartment , Deschutes River Woods
This one-bedroom apartment at Seventh Mountain Resort in Central Oregon, offering access to Deschutes National Forest recreation, is ideally situated for exploring the region's natural beauty.
The self-catering flat sleeps four, boasts a swimming pool, jacuzzi, fitness centre, and parking, and benefits from the resort's back-to-school deals.

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

Riverside Cottage - Just Steps From The Deschutes - Bend, OR
9.4 59 reviews
Bend, OR
06/08 – 09/08
SG$557/nighttotal: SG$1671 (3 )

Riverside Cottage - Just Steps From The Deschutes

1 2
apartment , Bend
This riverside flat in Bend's River West district offers direct access to the Deschutes River and is just a short walk to downtown attractions.
This 42 square meter flat accommodates up to four guests, features a kitchenette, air conditioning, and access to an indoor heated swimming pool and Jacuzzi, with pets welcome for an additional fee.
Riverfront Condo W/ Pool And Hot Tub Access - Bend, OR
9.2 5 reviews
Bend, OR
22/07 – 24/07
SG$418/nighttotal: SG$836 (2 )

Riverfront Condo W/ Pool And Hot Tub Access

1 2
apartment , Bend
This riverside flat in Bend's River West district offers direct access to the Deschutes River trail, leading to downtown Bend, and boasts excellent user ratings.
This 60 square metre apartment, suitable for four guests, features a fully equipped kitchen, two bathrooms including a walk-in shower, a private patio, an indoor heated pool, and a hot tub, with pets allowed for an additional fee.
Big Pine Home On Deschutes River Trail - Bend, OR
9.7 174 reviews
Bend, OR
17/09 – 19/09
SG$563/nighttotal: SG$1126 (2 )

Big Pine Home On Deschutes River Trail

3 2
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.
The Garden Apt-hot Tub Fireplace Ac 250+ Mbps - Bend, OR
9.9 945 reviews
Bend, OR
14/08 – 16/08
SG$330/nighttotal: SG$660 (2 )

The Garden Apt-hot Tub Fireplace Ac 250+ Mbps

1 2
apartment , Bend
This charming one-bedroom apartment is situated in Bend's River West neighbourhood, just a short walk from the city centre and close to the Deschutes River and Drake Park. The apartment has received excellent ratings for its location, cleanliness, and user experience.
The apartment is ideal for couples or solo travellers and features a loft with a pull-out sofa, a clawfoot bath, and a small private balcony. Guests can enjoy access to a shared saltwater hot tub, outdoor grill, fenced backyard, laundry facilities, and bike storage, along with a well-equipped kitchenette and a comfortable bedroom.

Best Bend, OR holiday rentals with parking

Stunning Riverfront Studio With Pool And Hot Tub - Bend, OR
Bend, OR
03/07 – 05/07
SG$482/nighttotal: SG$964 (2 )

Stunning Riverfront Studio With Pool And Hot Tub

1 2
studio , Bend
This studio apartment in Bend offers riverfront mountain views and is an 18-minute walk from Drake Park, with Hollinshead Park located 1.4 miles away.
This 40-square-meter self-catering apartment accommodates up to three guests and features a fully equipped kitchen, air conditioning, WiFi, an indoor swimming pool, and a hot tub.
King Bed - Pet Friendly - Ev Charger - Emersens Place - Bend, OR
9.6 298 reviews
Bend, OR
19/08 – 20/08
SG$744/nightfor 1 night

King Bed - Pet Friendly - Ev Charger - Emersens Place

3 4
apartment , Bend
This Bend holiday home, located in the Old Farm District, is under 3.2km from Bend Rock Gym, Bend Factory Stores, and within 4.8km of the Old Mill District.
The 118 square metre property sleeps six guests in three bedrooms and two bathrooms, boasting a private garden, spa, tennis court, and barbecue facilities alongside free Wi-Fi.
Premiere Suite With Access To Pools, Hot Tub, Spa - Bend, OR
9.8 6 reviews
Bend, OR
19/08 – 20/08
SG$513/nightfor 1 night

Premiere Suite With Access To Pools, Hot Tub, Spa

1 4
apartment , Bend
This Boyd Acres apartment in Bend, Oregon is situated near the Bend River Promenade and Deschutes River, with Sun Mountain Fun Center and River's Edge Golf Course less than 1.6km away.
The one-bedroom, one-bathroom flat sleeps four guests and boasts an indoor pool, hot tub, private balcony, free Wi-Fi, and limited housekeeping, offering a convenient base for exploring Bend's attractions.
170 M² House ∙ 3 Bedrooms ∙ 6 Guests - Bend, OR
9.8 19 reviews
Bend, OR
18/07 – 08/08
SG$822/nighttotal: SG$17262 (21 )

170 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 2
house , Bend
This Bend property is situated at the base of Pilot Butte State Scenic Viewpoint, offering immediate access to hiking trails and proximity to Whole Foods Market and various restaurants within a few minutes' drive.
This 169 square metre (1819 square feet) three-bedroom, three-bathroom house sleeps six, boasting a gourmet kitchen, a hot tub, a swimming pool, and a fitness centre, perfect for a family getaway.
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