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

Holiday Homes in Bend

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Bend holiday homes

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

Walk to River, Downtown, Concerts · Old Bend Cottage
Old Bend
9.0 out of 10, Wonderful, (16 reviews)
"Great place close to the river, shops, and restaurants. Loved the old Bend charm and the modern amenities. Will definitely stay here again."
United States
Jennifer B.
The price is NZ$435
includes taxes & fees
3 Nov - 4 Nov
Walk to River, Downtown, Concerts · Old Bend Cottage

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 NZ$413
includes taxes & fees
1 Nov - 2 Nov
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

3. 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 NZ$542
includes taxes & fees
30 Oct - 31 Oct
Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.

4. 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 NZ$396
includes taxes & fees
8 Nov - 9 Nov
Blue Spruce Guesthouse - Walkable to river trail and downtown Bend

5. 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 NZ$321
includes taxes & fees
31 Oct - 1 Nov
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby

6. 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.
Bluebird Day - Lava Hideaway, Retreat in Bend with King bed, perfect for couples!

7. 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, (42 reviews)
"Small but cute and everything you need for a couple staying for a few days!"
United States
Anonymous traveller
Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet

8. 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.
The price is NZ$409
includes taxes & fees
1 Nov - 2 Nov
Middle Sister - Sweet Bungalow, Queen bed, Parking, Walkable downtown Bend

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

Historic Craftsman Bungalow, Just Steps to Downtown ~HOT TUB!~
Old Bend
10.0 out of 10, Exceptional, (218 reviews)
"Property was beautiful, decor and floor plan exceeded our expectations, so many amenities in close walking distance."
United States
Judy C.
The price is NZ$891
includes taxes & fees
19 Nov - 20 Nov
Historic Craftsman Bungalow, Just Steps to Downtown ~HOT TUB!~

10. 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, (112 reviews)
"Really cute place and I would definitely stay here again!"
United States
Krista N.
The price is NZ$579
includes taxes & fees
31 Oct - 1 Nov
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba

11. 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.
Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!

12. 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.
Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.

13. 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

14. 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.

15. 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.
Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.

16. 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 NZ$518
includes taxes & fees
2 Nov - 3 Nov
Newly renovated and 3 minute walk to the center of downtown!

17. 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 NZ$537
includes taxes & fees
1 Nov - 2 Nov
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard

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

Romantic Guest House on 20 acres - Hot tub, Wildlife, Amazing Pool, Tennis Court
Bend
10.0 out of 10, Exceptional, (154 reviews)
"If you are looking for peace and tranquility, this is it!"
United States
Bruce
The price is NZ$558
includes taxes & fees
1 Nov - 2 Nov
Romantic Guest House on 20 acres - Hot tub, Wildlife, Amazing Pool, Tennis Court

19. Adorable Tiny Home │East Side Near Park │Extended Stays Welcome │ Private Home

Adorable Tiny Home │East Side Near Park │Extended Stays Welcome │ Private Home
Orchard District
9.8 out of 10, Exceptional, (18 reviews)
"Awesome and extremely peaceful stay.......thank you and cheers....."
United States
Sara T.
Adorable Tiny Home │East Side Near Park │Extended Stays Welcome │ Private Home

20. 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 NZ$493
includes taxes & fees
8 Nov - 9 Nov
West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bend Hotel Reviews

Find out more about Bend

Bend Holiday Homes information

Number of reviews
1,074
Accommodation
2703 Holiday Homes
Lowest Price
NZ$321
Highest Price
NZ$891