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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Bend vacation homes

A building with a green door and a wooden exterior.

1. 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 CA $174
CA $406 total
includes taxes & fees
Oct 20 - Oct 21
Bluebird Day - Lava Hideaway, Retreat in Bend with King bed, perfect for couples!
A single-story house with a green door, a small porch, and a brick entrance.

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

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
River West
10.0 out of 10, Exceptional, (47 reviews)
"This place is beautiful and the location was excellent! Our hosts were very attentive and the binder of local information was most appreciated!"
United States
Christine R.
The price is CA $167
CA $335 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
A modern interior with a wooden dining table, a red chair, a bed with a white bedspread, and a ceiling fan.

3. 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 CA $141
CA $321 total
includes taxes & fees
Oct 21 - Oct 22
Blue Spruce Guesthouse - Walkable to river trail and downtown Bend
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.

4. 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)
"Lovely, clean, peaceful place to stay, and wonderful hosts!"
United States
Veronica M.
The price is CA $123
CA $257 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
A kitchen with wooden cabinets, a granite countertop, a stainless steel sink, a microwave, and a stove.

5. 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 CA $161
CA $415 total
includes taxes & fees
Oct 20 - Oct 21
Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.
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

Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
Larkspur
10.0 out of 10, Exceptional, (41 reviews)
"Small but cute and everything you need for a couple staying for a few days!"
United States
Anonymous traveller
The price is CA $137
CA $288 total
includes taxes & fees
Oct 19 - Oct 20
Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
A spacious kitchen with dark wooden cabinets, stainless steel appliances, and a large island.

7. 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 CA $160
CA $389 total
includes taxes & fees
Oct 20 - Oct 21
Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.
A modern house with a green door, number 1056, and a small patio with two chairs.

8. 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 CA $146
CA $375 total
includes taxes & fees
Oct 21 - Oct 22
Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!
A modern kitchen with a gas stove, stainless steel appliances, and a granite countertop.

9. 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 CA $174
CA $411 total
includes taxes & fees
Oct 18 - Oct 19
Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.
A spacious living area with a wooden floor, a sofa, a dining table, and a kitchen in the background.

10. Backyard Oasis 8min to Town Fast Wi-fi

Backyard Oasis 8min to Town Fast Wi-fi
2.0 star property
Mountain View
The price is CA $166
CA $409 total
includes taxes & fees
Oct 18 - Oct 19
Backyard Oasis 8min to Town Fast Wi-fi
A spacious kitchen with a dining area, a cozy seating area with a couch and chairs, and a large window with a mountain view.

11. 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 CA $123
CA $455 total
includes taxes & fees
Oct 16 - Oct 17
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."

12. 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 CA $183
CA $407 total
includes taxes & fees
Nov 8 - Nov 9
West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River
A kitchen with a white marble countertop, potted plants, and a window with a view of greenery.

13. 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, (86 reviews)
"Great property. Exactly what we were looking for. "
United States
Kelly
The price is CA $165
CA $484 total
includes taxes & fees
Oct 28 - Oct 29
Fantastic Location! Directly above river w/a 5 minute walk to downtown.
A covered porch with a blue door, a small table, and a metal railing.

14. 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, (110 reviews)
"Really cute place and I would definitely stay here again!"
United States
Krista N.
The price is CA $165
CA $439 total
includes taxes & fees
Oct 18 - Oct 19
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
A two-story house with a covered porch, a chimney, and a well-maintained lawn.

15. 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 CA $202
CA $485 total
includes taxes & fees
Oct 18 - Oct 19
Historic Cecil Sly House, Salt Hot Tub, Electric Charger, in Downtown
A spacious kitchen with a granite island, large windows, and a patio area with outdoor furniture.

16. 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 CA $133
CA $604 total
includes taxes & fees
Oct 19 - Oct 20
Relaxing gem on the green! Hot tub! Double Suite!
A house with a front porch, two Adirondack chairs, and a small garden.

17. *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 CA $242
CA $600 total
includes taxes & fees
Oct 18 - Oct 19
*NEW* Downtown Modern Nostalgia, completely updated and convenient
A spacious log cabin interior with a wooden floor, a leather sofa, a dining area, and a kitchen.

18. Lodge Vibes in the City - Large Log Home

Lodge Vibes in the City - Large Log Home
Mountain View
10.0 out of 10, Exceptional, (56 reviews)
"Great place! Would stay again. "
United States
nick c.
The price is CA $229
CA $466 total
includes taxes & fees
Oct 18 - Oct 19
Lodge Vibes in the City - Large Log Home
A living room with leather sofas, a wooden coffee table, a patterned rug, a white console table, and a hanging light fixture.

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

King Bed - Pet Friendly - EV Charger - Emersen’s Place
Old Farm District
9.8 out of 10, Exceptional, (37 reviews)
"Great stay! House as described and clean. Host helpful and responsive. "
United States
Rachel H.
The price is CA $166
CA $450 total
includes taxes & fees
Oct 28 - Oct 29
King Bed - Pet Friendly - EV Charger - Emersen’s Place
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
"modern design, clean room, comfortable bedding, breakfast included, airconditioning quiet, free parking"
gwendolin 1-night trip
Posted 1 hour ago
Hotel Peppertree Bend, BW Premier Collection

Find out more about Bend

Bend Vacation Homes information

Number of reviews
776
Accommodation
2703 Vacation Homes
Lowest Price
CA $257
Highest Price
CA $604

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