Vacation Rentals & Apartments in Bend

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Stroll the River or downtown from this Condo- In the heart of Bend

Bend condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$126

“Great, friendly and comfortable stay” Staying at this location was very welcoming and lovely. The location was very central in the city and close to many points of interest. It was easy to access and comfortable to stay in. The house is in great shape and was able to accommodate myself and my friends. I would definitely recommend this host and their home if you are looking for a comfortable night's stay.

Price per night from

$457

Hillside Haven

Bend house

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Price per night from

$158

Downtown Riverfront Cottage

Bend house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Tiny gem on a lovely river--and in a great town!” We've stayed in this tiny house now for three years and will be coming back. It's very small, true, but also very nicely equipped, and it gets great light. The Deschutes River out back gives the house the feel of being much larger. Downtown Bend, a ten-minute walk away, has more restaurants and watering holes than you could sample in a month, plus great shops. Mt. Bachelor is within a half hour drive for skiing vacations, and the Cascade Highway offers plenty of spectacular summer recreation choices. The house has one bedroom and a living room facing the river, plus a galley kitchen and a single bathroom. Think boxcar; the house is thin and long. No washer or dryer, but there's a very nice laundromat a few blocks away--and I'm picky about my laundry! If it weren't so efficiently laid out, it would be too small. Stay here with people you like a lot, because you won't be able to get away from them. But the river and the town will give you ample breathing room.

Price per night from

$269

Mt.Bachelor Village Resort--Comfortable living

Bend apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

“Cozy cottage! Great location in the heart of Bend!” Excelent location in Dowtown Bend! Walk to everything or bring your bike, kayak or skis! All ementities in cottage were first class with comfy bed and clean linens and towels! Owners are friendly and attentive but respect your privacy! Great patio and garden with BBQ for entertaining your guest. We will be back to the 2nd Street Cottage!!

Price per night from

$121

Responds fast! avg. 3 hours 48 minutes

Price per night from

$132

3 Mt Baker

Bend house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 20 minutes

Price per night from

$125

Bunk+Brew Historic Lucas House

Bend guest house

  • 7 bedrooms
  • 2 bathrooms
  • sleeps 28

Price per night from

$825

Price per night from

$456

Central Oregon Haven- Pet friendly, quiet, cozy and spacious living

Bend apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$109

Cairn

Bend house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

Responds fast! avg. 2 hours 20 minutes

Price per night from

$328

Responds fast! avg. 3 hours 48 minutes

Price per night from

$224

Couple Campervan (2 people)

Bend camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

Downtowner Apartment

Bend condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 20 minutes

Price per night from

$85

23 Quelah

Bend house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 20 minutes

Price per night from

$243

Family Campervan Rentals (up to 5 people)

Bend camper van

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$172

Furnished 30+ day rental close to Old Mill! Dog Friendly!

Bend house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$93

Price per night from

$227

Price per night from

$78

Price per night from

$178

Mirror Pond

Bend house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

Price per night from

$98

Price per night from

$83

Flagline Trail

Bend house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 20 minutes

Price per night from

$231

New Listing! Beautiful executive rental in Awbrey Butte!

Bend house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$189

Old Mill Magic

Bend condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

Price per night from

$109

Aspen Ridge

Bend house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Price per night from

$105

16 Yellow Pine

Bend house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 20 minutes

Price per night from

$117

Price per night from

$201

Jacksons Place

Bend house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Price per night from

$103

River Ridge 416B

Bend condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 20 minutes

Price per night from

$81

Price per night from

$69

Price per night from

$533

Hollygrape Escape *30 Day Minimum

Bend house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

Price per night from

$219

Price per night from

$134

Trails End Retreat

Bend house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 20 minutes

Price per night from

$213

Price per night from

$181

Price per night from

$76

Viewing 38 of 290
rentals in Bend

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About Bend

Bend, Oregon

The largest city in Central Oregon, Bend is an outdoor lover’s paradise where you can pursue almost any outdoor activity you could dream of.

FlipKey has over 150 vacation rentals in Bend to choose from, so if you’re planning a trip here, you’re sure to find the perfect property to suit your needs and budget. 

About Bend, Oregon

Once known only by Native Americans, it wasn’t until 1824 that Bend was discovered by a fur trapping party. Bend became a logging town in the 1900s, and today it’s a haven for outdoor enthusiasts. Here you can enjoy fishing, hiking, mountain biking, camping, rock climbing – and almost any other outdoor pursuit you can think of.

The days here are hot and sunny, but temperatures can drop dramatically at night. This is even true in the summer months, so make sure you pack a sweater and jacket for your trip. Weather can be unpredictable, with hard frost not unheard of in the summer!

Bend has been dubbed ‘Beer Town USA’, thanks to the surprising number of breweries in the town. You simply must try the local dark brews. Mexican food here is also excellent, and you’ll find restaurants and cafes serving cuisine to suit all tastes and budgets.

What to do in Bend, Oregon

Come to Bend in the winter months and head for Mt Bachelor Ski Resort for skiing and snowboarding – the mountains get an average of 30ft of snow a year and kids ski for free! You can also enjoy a dog sled ride, rent a snowmobile or take a guided snowshoe tour.

In the summer months, hike the Oregon Desert Trail up to Horse Ridge for stunning views, explore Smith Rock State Park or discover the miles of lava tubes and caves running beneath the ground. It’s a region with fascinating geology and scenery to admire.

If you want to take to the water, you can go fishing for brown and rainbow trout in the Deschutes River, or try canoeing and kayaking at Sparks Lake or Elk Lake.

Bend has its fair share of shops too, with the Redmond Antique District great for vintage finds and The Old Mill District entertainment and shopping complex home to all your favorite brands.

Top travel tips for Ben, Oregon

The best way to get around is by bike as Bend has a network of bike lanes and paths. The bus service here is infrequent, taxis are hard to find and finding a parking spot during the day can be a challenge—bearing all that in mind, it’s best to explore downtown on foot!

The main airport is Redmond Airport-Roberts Field, a 15-minute drive from Bend. There are several shuttles available servicing the town, so getting from the airport to your rental is pretty easy. 

Mt Bachelor opens for winter activities from Thanksgiving weekend until mid-May and for summer activities from the start of July – it’s around 25 minutes’ drive from Bend.

Whether the snow is falling or the sun is shining, Bend is the ideal destination for an active vacation. FlipKey’s range of condos, log cabins and apartments in Bend means you’re sure to find the ideal property for your trip. Start searching today and find the perfect place to suit your style and budget.

Top Destination reviews

Cozy&Upscale Vacation Rental in Beautiful Bend offers 3 bedrooms, 2.5 baths
We had the most wonderful Christmas holiday in this lovely home!

Dorota met us at her lovely vacation rental home and made sure that we understood how to use all the electronics and amenities - of which there are many. :) The home is nicely furnished and accessorized with many of Dorota's own beautiful paintings (and Christmas decorations including a beautifully decorated live tree!) and photography and the kitchen is well equipped. The master bed was very comfortable; the bathroom is nice with a great shower head! A welcome treat after skiing - which is a short drive ... 20 min? away. Old Mill District about a 5 minute drive and the neighborhood was nice for walking in the winter wonderland. Friendly people - it feels very comfortable being there. We enjoyed walking our dog there. We liked the comfort and attractiveness of the home and it's easy location for shopping and/or skiing. We would definitely return and it would feel like home. … see more
Downtown Riverfront Cottage
Downtown Riverfront Cottage.

We've stayed in this house for a number of years. After the first stay we didn't want to stay anywhere else in Bend. Best dock on the River and a great location for easy access to downtown and Old Mill District. Easy walks. The owner lives next door and is a wealth of information on about anything the Bend area has to offer. Cozy house with everything we ever seem to need. Great queen bed and a sofa bed that is actually comfortable. Usually I can't stand them. Riverside Market is just a few blocks for an easy breakfast or lunch. Morning coffee on the dock and watch the river creatures wake up. We look forward to our stay every year. … see more
Exceptional downtown retreat/Cottage-choice Aug. & Sept. dates filling fast
Everything I needed!

I stayed in Don's cottage for a month while on a clinical rotation for school. I couldn't have asked for a more perfect place to stay. The cottage had everything I needed for a month long stay and it was quite cozy to come home to after a long day at work. It was also in a perfect location...only a few minutes walk to wonderful downtown Bend. Don was incredibly welcoming and accommodating for my entire stay. I would definitely stay in the cottage and would recommend it to anyone looking for a place to stay in Bend! … see more
Mt.Bachelor Village Resort--Comfortable living
Great!

The condo was fantastic. It was well stocked with supplies and equipment and close to everything. Our family of four had a great time! … see more

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