Updating

Updating

Houses in Bend and Condos – Holiday Lettings - Holiday Rentals Bend

All filters

Filters

223 Holiday homes

Condo rental in Bend

Bend condo

1 bedroom • 2 bathrooms • sleeps 4

from £92 / night

£664 / week

1 / 22

Home rental in Bend

Bend house

2 bedrooms • 3 bathrooms • sleeps 6

from £334 / night

£2,339 / week

1 / 19

Holiday home in Bend

Bend house

1 bedroom • 1 bathroom • sleeps 4

from £150 / night

£871 - £1,328 / week

1 / 8

Holiday home in Bend

Bend house

8 bedrooms • 3 bathrooms • sleeps 10

from £132 / night

£924 / week

1 / 44

Apartment rental in Bend with tennis court

Bend apartment

1 bedroom • 1 bathroom • sleeps 4

from £126 / night

£880 / week

1 / 36

Bend holiday home rental

Bend house

4 bedrooms • 3 bathrooms • sleeps 12

from £107 / night

£750 / week

1 / 28

Holiday home in Bend

Bend house

3 bedrooms • 2 bathrooms • sleeps 7

“Great location, beautiful corner of the Cascades!” This home was just perfect for our group of 3 couples who get together each year for some some fun in the mountains. We love backcountry ski touring, cycling, trail running, campfires, and breweries - and Bend has it all! The outdoor fireplace and hot tub made a perfect place to unwind after a long day in the mountains, and the location of this home was very convenient to either head into town, up to the mountains, or just step out the door for miles of road to explore on the run or bike. Each of the 3 bedrooms were cozy and comfortable, and we made good use of the well appointed kitchen and barbecue for home cooked meals. We went into town a couple of nights to sample some of the many microbreweries - 10 Barrel and Good Life being two of our favorites. From the common location at the base of Mt. Bachelor, our group was able to xc ski, backcountry skin up to Broken Top/Sisters Wilderness, or downhill ski, and then meet back up at the end of the day without any hassle. The owner was very helpful in answering our questions and represented the property accurately. We would without hesitation stay at Tumalo Pines again!

from £252 / night

£1,765 / week

1 / 18

Holiday cottage with golf nearby in Bend

Bend cottage

1 bedroom • 1 bathroom • sleeps 4

“The perfect place to stay in Bend!” We loved everything about our stay in Bend. The 2nd Street Cottage was awesome... Clean, quiet, close to downtown and very relaxing! Don is an incredible host, making sure we were enjoying our time. He even surprised us with a bottle of champagne for our anniversary night! He gave us directions to great hikes and a wonderful drive, perhaps one of most memorable times of the trip. The patio is wonderful, wish we could have enjoyed that more. The only problem with our stay was that we didn't stay longer! We would love to return someday, maybe bring the kids next time!

from £229 / night

£1,490 / week

1 / 28

Holiday guest house in Bend

Bend guest house

7 bedrooms • 2 bathrooms • sleeps 28

from £600 / night

£4,196 / week

1 / 34

Holiday home letting

Bend house

1 bedroom • 1 bathroom • sleeps 4

from £188 / night

£1,313 / week

1 / 52

Bend holiday home rental

Bend house

5 bedrooms • 3 bathrooms • sleeps 12

from £208 / night

£1,452 - £1,975 / week

1 / 16

Bend holiday home rental

Bend house

2 bedrooms • 2 bathrooms • sleeps 5

from £150 / night

£1,046 / week

1 / 36

Home rental in Bend

Bend house

3 bedrooms • 2 bathrooms • sleeps 6

from £415 / night

£2,909 / week

1 / 12

Holiday apartment with golf nearby in Bend

Bend apartment

1 bedroom • 1 bathroom • sleeps 4

from £79 / night

£498 / week

1 / 31

Log cabin rental in Bend

Bend log cabin

2 bedrooms • 1 bathroom • sleeps 6

from £324 / night

£2,267 / week

1 / 45

Holiday home with shared pool, golf nearby in Bend

Bend house

4 bedrooms • 4 bathrooms • sleeps 12

from £193 / night

£1,348 / week

1 / 25

Bend holiday home rental

Bend house

5 bedrooms • 5 bathrooms • sleeps 13

from £220 / night

£1,539 / week

1 / 38

Log cabin rental in Bend

Bend log cabin

3 bedrooms • 2 bathrooms • sleeps 6

from £71 / night

£494 / week

1 / 23

Bend ski camper van to rent.

Bend camper van

1 bedroom • 1 bathroom • sleeps 2

from £125 / night

£875 / week

1 / 8

Holiday apartment in Bend

Bend apartment

1 bedroom • 1 bathroom • sleeps 4

from £111 / night

£773 / week

1 / 45

Holiday home rental

Bend house

2 bedrooms • 1 bathroom • sleeps 7

from £195 / night

£1,362 / week

1 / 46

Bend ski camper van to rent.

Bend camper van

2 bedrooms • 1 bathroom • sleeps 5

from £125 / night

£875 / week

1 / 10

Bend holiday condo rental

Bend condo

1 bedroom • 1 bathroom • sleeps 4

from £62 / night

£430 / week

1 / 17

Holiday home in Bend

Bend house

6 bedrooms • 6 bathrooms • sleeps 16

from £176 / night

£1,232 / week

1 / 47

Holiday home in Bend

Bend house

4 bedrooms • 3 bathrooms • sleeps 8

from £155 / night

£1,081 / week

1 / 31

Holiday home rental

Bend house

3 bedrooms • 2 bathrooms • sleeps 6

from £106 / night

£738 / week

1 / 32

Ski home to rent in Bend

Bend house

3 bedrooms • 2 bathrooms • sleeps 7

from £129 / night

£901 / week

1 / 12

Bend holiday condo rental

Bend condo

2 bedrooms • 2 bathrooms • sleeps 4

from £68 / night

£477 / week

1 / 31

Holiday home in Bend

Bend house

3 bedrooms • 3 bathrooms • sleeps 8

from £94 / night

£657 / week

1 / 36

Holiday home in Bend

Bend house

5 bedrooms • 2 bathrooms • sleeps 12

from £176 / night

£1,003 - £3,456 / week

1 / 39

Holiday home in Bend

Bend house

2 bedrooms • 2 bathrooms • sleeps 6

from £82 / night

£570 / week

1 / 20

Holiday cottage in Bend

Bend cottage

1 bedroom • 1 bathroom • sleeps 2

from £75 / night

£516 - £1,249 / week

1 / 24

Holiday home in Bend

Bend house

5 bedrooms • 4 bathrooms • sleeps 12

from £180 / night

£1,255 / week

1 / 55

Holiday home in Bend

Bend house

4 bedrooms • 3 bathrooms • sleeps 8

from £184 / night

£1,284 / week

1 / 65

Bend holiday home rental

Bend house

3 bedrooms • 3 bathrooms • sleeps 8

from £106 / night

£738 / week

1 / 31

Holiday home in Bend

Bend house

4 bedrooms • 3 bathrooms • sleeps 8

from £159 / night

£1,110 / week

1 / 31

Bend holiday home rental

Bend house

5 bedrooms • 2 bathrooms • sleeps 12

from £385 / night

£2,695 / week

1 / 15

Holiday home in Bend

Bend house

2 bedrooms • 2 bathrooms • sleeps 6

from £125 / night

£735 - £1,653 / week

1 / 25

Holiday home in Bend

Bend house

3 bedrooms • 2 bathrooms • sleeps 8

from £88 / night

£610 / week

1 / 38

Bend holiday home rental

Bend house

3 bedrooms • 2 bathrooms • sleeps 7

from £79 / night

£552 / week

1 / 35

×

Bend holidays

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.

Holiday Lettings has over 150 holiday 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 favourite 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 holiday. Holiday Lettings’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.

Also consider