Birch trees with yellow leaves, a lake, and a snow-capped mountain in the background.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Bend holiday homes

A room with a wooden ceiling, a large window with a view of trees, a flat-screen TV, a dark-colored sofa, and a wooden bench.

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

Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
River West
10.0 out of 10, Exceptional, (43 reviews)
"Great host and quick walk to downtown!"
United States
jeremy h.
The price is HK$678
HK$1,417 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
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

Blue Spruce Guesthouse - Walkable to river trail and downtown Bend
River West
10.0 out of 10, Exceptional, (41 reviews)
"Great stay "
United States
donna t.
The price is HK$777
HK$1,774 total
includes taxes & fees
22 Oct - 23 Oct
Blue Spruce Guesthouse - Walkable to river trail and downtown Bend
A building with a green door and a wooden exterior.

3. Bluebird Day - Lava Hideaway, Retreat in Bend with King bed, perfect for couples!

Bluebird Day - Lava Hideaway, Retreat in Bend with King bed, perfect for couples!
Old Bend
9.6 out of 10, Exceptional, (99 reviews)
"We loved staying here! Location was great and we were able to enjoy the walking paths and local shops!"
United States
Abbie L.
The price is HK$969
HK$2,269 total
includes taxes & fees
21 Oct - 22 Oct
Bluebird Day - Lava Hideaway, Retreat in Bend with King bed, perfect for couples!
A kitchen with wooden cabinets, a granite countertop, a stainless steel sink, a microwave, and a stove.

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

Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.
Old Bend
10.0 out of 10, Exceptional, (14 reviews)
"Responsive host and great location"
United States
Maureen K.
The price is HK$891
HK$2,308 total
includes taxes & fees
21 Oct - 22 Oct
Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.
A two-story wooden house with a front porch, number 104, and a small garden area.

5. Historic Bungalow in Walkable Old Bend

Historic Bungalow in Walkable Old Bend
Old Bend
10.0 out of 10, Exceptional, (20 reviews)
"Amazing location, would definitely recommend."
United States
Matthew U.
Historic Bungalow in Walkable Old Bend
A modern kitchen with a gas stove, stainless steel appliances, and a granite countertop.

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

Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.
Old Bend
9.6 out of 10, Exceptional, (15 reviews)
"Great location easy to find and access"
United States
kathy b.
The price is HK$960
HK$2,259 total
includes taxes & fees
21 Oct - 22 Oct
Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.
A two-story wooden house with a porch, outdoor seating, and a fenced garden.

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

Middle Sister - Sweet Bungalow, Queen bed, Parking, Walkable downtown Bend
Old Bend
10.0 out of 10, Exceptional, (3 reviews)
"Location, location, location. Stone's Throw Bungalow is in walking distance to everything in Bend (e.g., downtown, Hayden Homes Amphitheater, etc.). The bungalow itself was very clean, had everything we needed (full kitchen), parking spot, etc. I would highly recommend staying to anyone passing through Bend!"
United States
Nicholas K.
Middle Sister - Sweet Bungalow, Queen bed, Parking, Walkable downtown Bend
A spacious kitchen with dark wooden cabinets, stainless steel appliances, and a large island.

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

Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.
Old Bend
9.8 out of 10, Exceptional, (9 reviews)
"Great property and location!"
United States
Patrick W.
The price is HK$882
HK$2,163 total
includes taxes & fees
21 Oct - 22 Oct
Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.
A living room with a fireplace, a television mounted above it, and a cozy seating area with a sofa and a coffee table.

9. Gather! A Welcoming Home - King Beds - Pool Table!

Gather! A Welcoming Home - King Beds - Pool Table!
Mountain View
10.0 out of 10, Exceptional, (36 reviews)
"Easy and simple one night stay"
United States
Mark T.
Gather! A Welcoming Home - King Beds - Pool Table!
A modern house with a green door, number 1056, and a small patio with two chairs.

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

Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!
River West
9.6 out of 10, Exceptional, (25 reviews)
"Wonderful accommodations in a great location!"
United States
Caroline W.
The price is HK$805
HK$2,059 total
includes taxes & fees
21 Oct - 22 Oct
Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!
A kitchen with a white marble countertop, potted plants, and a window with a view of greenery.

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

Fantastic Location! Directly above river w/a 5 minute walk to downtown.
River West
10.0 out of 10, Exceptional, (87 reviews)
"Great property. Exactly what we were looking for. "
United States
Kelly
Fantastic Location! Directly above river w/a 5 minute walk to downtown.
A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a bar area with stools.

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

Newly renovated and 3 minute walk to the center of downtown!
River West
9.6 out of 10, Exceptional, (17 reviews)
"Perfect location for enjoying downtown Bend."
United States
Kelly K.
The price is HK$826
HK$2,303 total
includes taxes & fees
21 Oct - 22 Oct
Newly renovated and 3 minute walk to the center of downtown!
A spacious kitchen with a dining area, a cozy seating area with a couch and chairs, and a large window with a mountain view.

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

Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
Redmond
9.8 out of 10, Exceptional, (55 reviews)
"Great location and amazing property!"
United States
Kim b.
The price is HK$600
HK$2,388 total
includes taxes & fees
21 Oct - 22 Oct
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
A wooden building with a porch, a red door, and a sign that reads "GRAPE WEST ENGLAND."

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

West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River
River West
9.8 out of 10, Exceptional, (80 reviews)
"Great stay-walkable location, charming home with great fenced backyard and outdoor space. Will definitely stay again!"
United States
Paula M.
The price is HK$1,012
HK$2,248 total
includes taxes & fees
8 Nov - 9 Nov
West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River
A covered porch with a blue door, a small table, and a metal railing.

15. Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba

Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
Orchard District
9.4 out of 10, Exceptional, (111 reviews)
"Really cute place and I would definitely stay here again!"
United States
Krista N.
The price is HK$911
HK$2,390 total
includes taxes & fees
25 Oct - 26 Oct
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
A house with a white exterior, a trailer, and a car parked near a body of water with reflections.

16. Cozy cottage with river access and great outdoor adventures

Cozy cottage with river access and great outdoor adventures
La Pine
8.8 out of 10, Excellent, (35 reviews)
"The cottage was very comfortable, not as clean as I wished but ok. The kitchen needs dish rags and drying towels, only having sponges was not what I would have liked."
United States
Anna
The price is HK$558
HK$998 total
includes taxes & fees
21 Oct - 22 Oct
Cozy cottage with river access and great outdoor adventures
A kitchen with dark wooden cabinets, a stainless steel sink, and a marble countertop.

17. ***NEW*** Charming home located in Downtown Bend!

***NEW*** Charming home located in Downtown Bend!
River West
9.8 out of 10, Exceptional, (8 reviews)
"5 stars"
United States
Angelica L.
The price is HK$1,130
HK$3,407 total
includes taxes & fees
25 Oct - 26 Oct
***NEW*** Charming home located in Downtown Bend!
A spacious kitchen with a granite island, large windows, and a patio area with outdoor furniture.

18. Relaxing gem on the green! Hot tub! Double Suite!

Relaxing gem on the green! Hot tub! Double Suite!
Century West
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location and facility"
United States
Gritters F.
The price is HK$731
HK$3,286 total
includes taxes & fees
22 Oct - 23 Oct
Relaxing gem on the green! Hot tub! Double Suite!
A two-story house with a covered porch, a chimney, and a well-maintained lawn.

19. Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown

Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown
Old Bend
10.0 out of 10, Exceptional, (45 reviews)
"Location was great, being able to walk downtown and drake park was great. We usually stay on the west side when visiting family but this location was even better. The house had tasteful updates without losing the charming feel. We will look to rent here first when visiting family next."
United States
Tyler S.
The price is HK$1,113
HK$2,641 total
includes taxes & fees
22 Oct - 23 Oct
Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown
A house with a front porch, two Adirondack chairs, and a small garden.

20. *NEW* Downtown Modern Nostalgia, completely updated and convenient

*NEW* Downtown Modern Nostalgia, completely updated and convenient
River West
9.6 out of 10, Exceptional, (48 reviews)
"Nice property 6 blocks from downtown."
United States
Lynn B.
The price is HK$1,334
HK$3,302 total
includes taxes & fees
21 Oct - 22 Oct
*NEW* Downtown Modern Nostalgia, completely updated and convenient
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bend Hotel Reviews

Hotel Peppertree Bend, BW Premier Collection

Hotel Peppertree Bend, BW Premier Collection

10/10 Excellent
"Clean room. Good location for many dining options. The bed was not as comfortable as previous stays, but everything else about the stay was good. Staff was helpful"
Marcella 2-night trip
Posted 4 hours ago
Hotel Peppertree Bend, BW Premier Collection

Find out more about Bend

Bend Vacation Homes information

Number of reviews
680
Accommodation
2703 Vacation Homes
Lowest Price
HK$998
Highest Price
HK$3,407

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