Villas and Holiday homes in Bend, OR

This family-friendly holiday cottage in Bend offers proximity to the Deschutes River and the mountains, with hiking and biking routes within a 1-kilometre radius, and easy access to the area's natural beauty.
This four-bedroom property accommodates up to nine guests and features a fully-equipped kitchen, a gas fireplace, a private garden with a grill and fire pit, and access to community amenities including a swimming pool and park, with a 30-day minimum stay requirement.

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.

This charming cottage is located in River West, Bend, offering convenient access to the Hayden Homes Amphitheater and the Des Chutes Historical Museum, with a water park nearby.
This 56 square meter dwelling accommodates two guests and features a well-equipped kitchen with a fridge and microwave, air conditioning, a garden, a spa, and parking, with the added benefit of internet access and allowing pets.

This pet-friendly holiday home is situated in Bend's Midtown, a short walk from Hollinshead Park and a few miles (approximately 5km and 4km respectively) from Drake Park and Ponderosa Park.
The 146 square metre property boasts three bedrooms, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen with dishwasher and microwave, free Wi-Fi, a garden, and parking.

This Bend holiday home is peacefully situated near the Deschutes River, 4.8km from Bend city centre and 2.4km from the Old Mill District.
The 124 square metre single-storey property boasts three bedrooms, two bathrooms, sleeps seven, and features a gourmet kitchen, hot tub, swimming pool, and private garden, with easy access to nature trails.

Brightenwood House, situated in the Brightenwood neighbourhood of Bend, Oregon, is a short drive from Bend's city centre and its attractions.
This two-bedroom, two-bathroom property sleeps four guests in a king and queen ensuite, offering two separate units, a fully fenced garden with BBQ and smoker, plus a spa, fitness centre, and on-site restaurant; a 10% discount applies to bookings of a week or more (excluding Christmas/New Year).

This detached house, located in Southwest Bend, is set within 0.8 kilometres of downtown Bend's breweries, food carts, shopping, and live music venues, offering a secluded setting surrounded by Ponderosa pines.
Accommodation for up to six guests is provided across three bedrooms, featuring a fully equipped kitchen, air conditioning, a hot tub, and ample parking suitable for bikes, paddleboards, trailers, and boats.

This Westside Bend dwelling is located a few blocks from Newport Market and a short walk to the Deschutes River, downtown Bend's dining establishments and breweries, offering excellent walkability.
This 112 square meter house accommodates up to four guests with two bedrooms and two bathrooms, featuring a private patio with a hot tub, a kitchen with a fridge, microwave and dishwasher, air conditioning, a swimming pool, a gym, and private alley-access parking with an EV charger, ideal for exploring Mt. Bachelor, biking, hiking and fishing.

Ski House 144 is located in Bend, just 3.8 kilometres from Drake Park, 7.4 kilometres from Hollinshead Park, and 5.8 kilometres from Ponderosa Park, offering easy access to outdoor recreation and scenic views. The accommodation has received very good ratings for cleanliness and user experience, and an excellent rating for location.
The property has one bathroom and can accommodate up to four guests. It features a fully equipped kitchen, a private balcony, free Wi-Fi, air conditioning, a swimming pool, a jacuzzi, a garden, and free parking, making it an ideal choice for families and groups looking for a comfortable and convenient stay in Bend.

The Osprey is situated in Bend, just over 3 miles from Drake Park and about 5 miles from Hollinshead Park, in a location perfect for skiing enthusiasts. The property has received excellent ratings for its cleanliness, location and overall user experience.
The 4-bedroom property provides comfortable accommodation for up to 10 guests across its 168 square metres. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, and parking.

This detached house in Bend is located a short drive from Drake Park (4.3 km), Ponderosa Park (5.9 km), and Hollinshead Park (8 km), with Redmond Municipal Airport 30.6 km away and an ice-skating rink nearby.
This 283 square metre holiday home offers four bedrooms, three bathrooms, accommodates up to 19 guests, and features a swimming pool, fitness centre, tennis court, on-site parking, air conditioning, a fireplace, and a barbecue, with complimentary WiFi available in public areas.

This modern one-bedroom guesthouse is situated within 4.8 kilometres of the Deschutes River, Old Mill, Box Factory, and Downtown Bend, and is within walking distance of Spider Brewing, Bevel Brewing, and Cascade Lakes Brewery.
This self-contained accommodation offers a fully equipped kitchen, air conditioning, and dedicated workspace, comfortably accommodating up to three guests with excellent ratings for cleanliness and location.

This riverfront condominium in Bend is situated 1.3 kilometres from Hollinshead Park and a 15-minute walk from Drake Park.
This property offers 59 square metres of living space, accommodates up to 7 guests, and features an indoor swimming pool, a hot tub, and complimentary WiFi.

This ground floor riverside cottage in Bend is located 1.3 kilometres from Drake Park and 2.1 kilometres from Hollinshead Park, with Ponderosa Park 4 kilometres away.
This 60 square meter accommodation offers a private entrance, air conditioning, an indoor swimming pool, a hot tub, a kitchen with a fridge and microwave oven, and parking for up to 7 guests.

This Dara Oaks property in Bend is located 4.8 kilometres from Hollinshead Park, 7.9 kilometres from Drake Park and 7.7 kilometres from Ponderosa Park.
This 5-bedroom, 3-bathroom house offers accommodation for up to 27 guests, featuring a private swimming pool, a well-equipped kitchen with a dishwasher and oven, air conditioning, a fireplace, complimentary WiFi, and private parking, with skiing opportunities nearby.

Old Mill Getaway is a family-friendly house in Bend, Oregon, situated a short distance (approximately 1 kilometre) from the Old Mill District, Bevel Brewing, and Spider City Brewing.
This 161 square metre property sleeps nine guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, a private backyard with a hot tub, and parking for up to four vehicles; enjoy nearby outdoor recreation and AvantStay's concierge services.