Bend Holiday Homes from £155: Search Holiday Homes in Bend

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Our top choices for Bend holiday homes

A modern house with a green door, number 1056, and a small patio with two chairs.

1. Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!

River West

Caroline W.

includes taxes & fees

9 Nov - 10 Nov

A modern interior with a wooden dining table, a red chair, a bed with a white bedspread, and a ceiling fan.

2. Blue Spruce Guesthouse - Walkable to river trail and downtown Bend

River West

Todd W.

includes taxes & fees

8 Nov - 9 Nov

A single-story house with a green door, a small porch, and a brick entrance.

3. Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

River West

Christine R.

includes taxes & fees

12 Nov - 13 Nov

A hallway with a wooden ceiling, a large window, a television, a sofa, a plant, and a rug.

4. Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby

River West

jeremy h.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a gas stove, stainless steel appliances, and a granite countertop.

5. Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.

Old Bend

kathy b.

includes taxes & fees

11 Nov - 12 Nov

A covered patio area with wooden lattice fencing, stone steps, and a potted plant.

6. Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet

Larkspur

Anonymous traveller

includes taxes & fees

11 Nov - 12 Nov

A small, single-story house with a porch, numbered 323, featuring two blue chairs and a small garden area.

7. Walk to River, Downtown, Concerts · Old Bend Cottage

Old Bend

Daniel

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, a mirror, a nightstand, and a door leading to a bathroom.

8. Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.

Old Bend

Maureen K.

includes taxes & fees

11 Nov - 12 Nov

A two-story wooden house with a porch, outdoor seating, and a fenced garden.

9. Middle Sister - Sweet Bungalow, Queen bed, Parking, Walkable downtown Bend

Old Bend

Nicholas K.

includes taxes & fees

8 Nov - 9 Nov

A house with a covered porch, a brick pathway, and surrounding greenery.

10. Parkridge at Pilot Butte - Warm & Modern Bend Ski/Outdoor Basecamp

Orchard District

Maryssa

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a bar area with stools.

11. Newly renovated and 3 minute walk to the center of downtown!

River West

Melina k.

includes taxes & fees

8 Nov - 9 Nov

A house with a covered porch, steps leading to the front door, and a well-maintained garden.

12. Historic Craftsman Bungalow, Just Steps to Downtown ~HOT TUB!~

Old Bend

Robin C.

includes taxes & fees

19 Nov - 20 Nov

A spacious kitchen with dark wooden cabinets, stainless steel appliances, and a large island.

13. Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.

Old Bend

Patrick W.

includes taxes & fees

19 Nov - 20 Nov

A spacious kitchen with a dining area, a cozy seating area with a couch and chairs, and a large window with a mountain view.

14. Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard

Redmond

Kim b.

A wooden building with a porch, a red door, and a sign that reads "GRAPE WEST ENGLAND."

15. West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River

River West

Josh W.

includes taxes & fees

9 Nov - 10 Nov

A spacious kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

16. Fantastic Location! Directly above river w/a 5 minute walk to downtown.

River West

Kelly

includes taxes & fees

11 Nov - 12 Nov

A living room with leather sofas, a wooden coffee table, a patterned rug, a white console table, and a hanging light fixture.

17. King Bed - Pet Friendly - EV Charger - Emersen’s Place

Old Farm District

Shuming C.

includes taxes & fees

17 Nov - 18 Nov

A bathroom with a granite countertop, wooden cabinets, a white toilet, and a glass-enclosed shower.

18. Romantic Guest House on 20 acres - Hot tub, Wildlife, Amazing Pool, Tennis Court

Bend

Bruce

includes taxes & fees

9 Nov - 10 Nov

A house with a front porch, two Adirondack chairs, and a small garden.

19. NEW Downtown Modern Nostalgia, completely updated and convenient

River West

Kevin M.

includes taxes & fees

8 Nov - 9 Nov

A kitchen with a large island, bar stools, a stainless steel refrigerator, and wooden cabinets.

20. King bed - Pet Friendly - Jameson's Place

Larkspur

Simply L.

includes taxes & fees

8 Nov - 9 Nov

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Bend and related destinations

Outdoor adventures await along the Deschutes River, where mountain biking trails and craft breweries create perfect day-to-night transitions. Hike through volcanic landscapes at Smith Rock State Park, then head city centre where even the fanciest restaurants welcome you in hiking boots.

See all hotels in Bend

A winter scene with a river, a bridge, buildings, and a tall tower with an American flag.

Top reviews in Bend

A fire pit with chairs around it, a red umbrella, and wooden buildings in the background.

Wall Street Suites

River West

10/10 Excellent

Christian

A balcony with a table set for breakfast, overlooking a forested area.

Pine Ridge Inn

Southern Crossing

10/10 Excellent

This hotel was gorgeous! Only stayed one night, but wished it was longer. We opted for a suite, which was huge, and came with a fireplace, a balcony, and a whirlpool bath. The setting was very quiet - you can see the river on one side. Breakfast was nice, but a bit limited in the selection available. Other reviews mentioned the bakery items, but the only bakery item was the croissants (pre-filled with ham and cheese). No hot food (although we knew this). None the less the overall stay was...

James