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

“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.

Price per night from

$454

Hillside Haven

Bend house

8 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 6 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.

Responds fast! avg. 2 hours 36 minutes

Price per night from

$330

Mt.Bachelor Village Resort--Comfortable living

Bend apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$171

Exceptional downtown retreat/Cottage- Winter 30+ night stays

Bend cottage

1 bedroom / 1 bathroom / sleeps 4

“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

$105

Price per night from

$258

3 Mt Baker

Bend house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 6 minutes

Price per night from

$134

Bunk+Brew Historic Lucas House

Bend guest house

7 bedrooms / 2 bathrooms / sleeps 28

Price per night from

$818

Blinn's Landing: Historic Log Cabin, Private Riverfront & Dock. Dog friendly.

Bend log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$475

Spacious 3 bedroom 2 bath house near Old Mill

Bend house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$567

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 6 minutes

Price per night from

$326

Albany

Bend log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 6 minutes

Price per night from

$97

Price per night from

$267

Couple Campervan (2 people)

Bend camper van

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

Downtowner Apartment

Bend condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 6 minutes

Price per night from

$85

23 Quelah

Bend house

6 bedrooms / 6 bathrooms / sleeps 16

Responds fast! avg. 2 hours 6 minutes

Price per night from

$242

Family Campervan Rentals (up to 5 people)

Bend camper van

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$171

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

Bend house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

Price per night from

$276

Price per night from

$98

Mid-town hideaway. Just minutes away from all that Bend has to offer.

Bend house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$177

Mirror Pond

Bend house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 6 minutes

Price per night from

$97

Price per night from

$98

Flagline Trail

Bend house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 2 hours 6 minutes

Price per night from

$229

New Listing! Beautiful executive rental in Awbrey Butte!

Bend house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$216

Old Mill Magic

Bend condo

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 6 minutes

Price per night from

$109

Wapiti Haven - rest, repose, relax in upscale comfort

Bend house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$439

Aspen Ridge

Bend house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 6 minutes

Price per night from

$158

16 Yellow Pine

Bend house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 6 minutes

Price per night from

$145

Price per night from

$235

Jacksons Place

Bend house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 6 minutes

Price per night from

$121

River Ridge 416B

Bend condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 6 minutes

Price per night from

$80

Bainbridge *30 day minimum*

Bend house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 6 minutes

Price per night from

$454

Price per night from

$81

Riverwoods Relaxation

Bend house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 6 minutes

Price per night from

$120

New Listing! Stunning Bend Bungalow - Walk to Downtown

Bend house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$587

Viewing 38 of 281
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

Beaver Drive 16539
Bend Oregon house

This was a special family vacation in a wonderful house on the Deschuttes river in Bend, OR. Very spacious and private, with a grill, deck and hot tub. Great views and lots to do. Village Properties staff were friendly and accommodating. Membership in the local sports club was a bonus: pool, yoga, gym, classes, etc. … see more
Mt Bachelor Village -Top floor with 2 Queen beds +
A Great Stay

Hi Tim and Nichole, We had a great stay at your condo. Everything worked just fine. It was wonderfully well equipped (a coffee grinder and oven would be handy). Your prompt response to my queries and transactions was much appreciated as was your detailed in-suite user manual. The complex was very pleasant -- quiet, park-like and very convenient to town. And Bend was wonderful -- attractive, clean, vibrant, historic - it has it all. It was a great stay. We'll be back. Thank you. All the best, you two. Peter and Randi Bruce Peter (and Randi) Bruce … see more
Light-filled 5BR, gameroom, hottub, ski, bike,golf
Everything we wanted and more!

I just wanted to drop you a line telling you how much we all enjoyed our stay at your beautiful house in Bend. Our pack of ten, 55+ year-olds, had so much fun hiking, biking, kayaking, shopping and visiting pubs! One member of our group does frequent trips and house rentals in other towns such as Moab and said that your house was by far the nicest setup they had ever rented! The house is very well appointed and was clean and ready for our arrival. The large open area on the main floor was great; people could be reading over in one corner yet they never missed out on the goings-on with the rest of the group and even the cooks in the kitchen were always aware of what the rest of us were up to and could quickly join in the merriment that developed. The location of the house worked well for our large and diverse group; downtown and the Old Mill District were a mere 5 minutes away by car and the main road to Mt. Bachelor and the Cascade Lakes area was just around the corner. On Saturdays, a 10 minute walk took you to the Farmers Market in the Northwest Crossing area. For those so inclined, a 20-30 minute stroll would take you to either Cascade Lakes Brewing Pub or to the Goodlife Brewery where one could sample some locally brewed beers and fine food. Volcano Winery is right next door to Goodlife for those who favor wines. I would have no problem recommending this house to friends and family. Any questions we had were answered promptly by the owner in a friendly and engaging manner. The pictures on the website are a true reflection of the house, there were no unpleasant surprises due to any camera trickery. Thanks again for letting us share your 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- Winter 30+ night stays
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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