A large, layered mountain with distinct geological formations.

Holiday Homes in Prineville

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Prineville holiday homes

A modern living room with a sofa, armchair, and dining area, featuring large windows and a view of a mountainous landscape.

1. Spectacular Smith Rock Views on 5 Acres - Quiet and Modern w/ King Beds

Spectacular Smith Rock Views on 5 Acres - Quiet and Modern w/ King Beds
Terrebonne
10.0 out of 10, Exceptional, (17 reviews)
"This was an amazing place. The house was beautiful and the location even better. Strongly recommend this place"
United States
eva j.
The price is €228
includes taxes & fees
4 Nov - 5 Nov
Spectacular Smith Rock Views on 5 Acres - Quiet and Modern w/ King Beds
A spacious kitchen with a dining area, a cozy seating area with a couch and chairs, and a large window with a mountain view.

2. 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.
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
A single-story house with a gray exterior, a front door, and a small porch.

3. Cozy Downtown Redmond Cottage

Cozy Downtown Redmond Cottage
Redmond
9.4 out of 10, Exceptional, (29 reviews)
"What a great location, walk all over town for coffee in the morning and food and drinks in the evening. Home is well stocked and comfortable."
United States
Taylor H.
Cozy Downtown Redmond Cottage
A living room with a sofa, a coffee table, a TV, and a dining area in the background.

4. Downtown Hub - Dog Friendly

Downtown Hub - Dog Friendly
Redmond
10.0 out of 10, Exceptional, (73 reviews)
"Great house great place to stay! "
United States
Matt w.
Downtown Hub - Dog Friendly
A modern building with an outdoor seating area featuring Adirondack chairs and a fire pit.

5. Private Retreat Steps to Smith Rock | Quiet Luxury & Hot Tub

Private Retreat Steps to Smith Rock | Quiet Luxury & Hot Tub
Terrebonne
10.0 out of 10, Exceptional, (12 reviews)
"We had a fantastic stay, can't wait ti book another relaxing get away"
United States
Genoa H.
The price is €549
includes taxes & fees
22 Nov - 23 Nov
Private Retreat Steps to Smith Rock | Quiet Luxury & Hot Tub
A modern kitchen with a central island, pendant lighting, and white cabinets.

6. Spacious downtown pad - billiards/ping pong/sauna

Spacious downtown pad - billiards/ping pong/sauna
Redmond
9.6 out of 10, Exceptional, (25 reviews)
"Location was nice being close to everything and the property was very inviting. If i come again, i would stay again if available = )"
United States
Sheila
Spacious downtown pad - billiards/ping pong/sauna
A living room with a fireplace, a television, a sofa, and a coffee table.

7. Romantic Resort Home Private Jacuzzi + Plush Robes

Romantic Resort Home Private Jacuzzi + Plush Robes
Redmond
9.8 out of 10, Exceptional, (44 reviews)
"Very well appointed and great location. Would definitely stay there again. Thanks Katya!"
United States
Sue S.
The price is €283
includes taxes & fees
10 Nov - 11 Nov
Romantic Resort Home Private Jacuzzi + Plush Robes
A kitchen with white cabinets, a marble countertop, a wine bottle, glasses, and a plant.

8. Downtown Redmond 4BR Walk to Food & Brews

Downtown Redmond 4BR Walk to Food & Brews
Redmond
10.0 out of 10, Exceptional, (2 reviews)
"Easy house for a weekend in Redmond!"
United States
Robyn L.
The price is €747
includes taxes & fees
1 Nov - 2 Nov
Downtown Redmond 4BR Walk to Food & Brews
A modern two-story house with a stone foundation, a garage, and a landscaped yard.

9. Eagle Crest Retreat | 6 Resort Passes Included

Eagle Crest Retreat | 6 Resort Passes Included
Redmond
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful owners that have everything you need and more to have a great stay at the top of eagle crest! Close to lakeside pool and only 8 minutes to the golf course."
United States
Jordan K.
Eagle Crest Retreat | 6 Resort Passes Included
An indoor swimming pool with a wooden ceiling and large windows.

10. Eagle Crest:9th Hole/Priv Hot Tub/Resort Amenities

Eagle Crest:9th Hole/Priv Hot Tub/Resort Amenities
Deschutes County
9.6 out of 10, Exceptional, (56 reviews)
"What a great place looking forward to coming back"
United States
Joseph O.
Eagle Crest:9th Hole/Priv Hot Tub/Resort Amenities
A spacious living room with a fireplace, a large clock, and a balcony with outdoor furniture.

11. Charming 3-bedroom townhome with WiFi, fitness room in peaceful Redmond

Charming 3-bedroom townhome with WiFi, fitness room in peaceful Redmond
Redmond
9.4 out of 10, Exceptional, (3 reviews)
"Great condo. Owner was quick to respond to any issues. the condo worked so good for our family vacation. Would stay here again for next vacation. "
United States
Sue R.
The price is €323
includes taxes & fees
3 Nov - 4 Nov
Charming 3-bedroom townhome with WiFi, fitness room in peaceful Redmond
A spacious living area with a leather sofa, a dining table, and a bar area with stools.

12. Eagle Crest Retreat on Golf course, Private w/View

Eagle Crest Retreat on Golf course, Private w/View
Redmond
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful Stay in this great house. Plenty of room, great deck, comfy furniture. Everything I was hoping for. The host (Heather) was easy to work with, friendly, and clear. The free access the to great Rec center was a nice added bonus. A!"
United States
Paul T.
The price is €338
includes taxes & fees
1 Nov - 2 Nov
Eagle Crest Retreat on Golf course, Private w/View
Interior

13. Eagle Crest Hole in One!

Eagle Crest Hole in One!
Redmond
10.0 out of 10, Exceptional, (5 reviews)
"This property was perfect for us. Great place to stay. "
United States
Laurie R.
Eagle Crest Hole in One!
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

14. New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views

New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views
Bend
10.0 out of 10, Exceptional, (5 reviews)
New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views
A single-story house with a front porch, a garage, and a well-maintained lawn.

15. Eagle Crest Desert Sky Retreat - HOT TUB, Dogs OK

Eagle Crest Desert Sky Retreat - HOT TUB, Dogs OK
Redmond
10.0 out of 10, Exceptional, (27 reviews)
"nice lawn area to take dogs out to. was able to block our small dogs on to patio with portable kennal"
United States
Laura B.
The price is €327
includes taxes & fees
2 Nov - 3 Nov
Eagle Crest Desert Sky Retreat - HOT TUB, Dogs OK
A small, single-story house with a porch, numbered 323, featuring two blue chairs and a small garden area.

16. 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 €243
includes taxes & fees
1 Dec - 2 Dec
Walk to River, Downtown, Concerts · Old Bend Cottage
A spacious log cabin interior with a wooden floor, a leather sofa, a dining area, and a kitchen.

17. 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 €288
includes taxes & fees
2 Nov - 3 Nov
Lodge Vibes in the City - Large Log Home
An outdoor patio area with a fire pit, seating, and string lights.

18. DogOk. Large Retreat, 3 King Beds. Fire pit

DogOk. Large Retreat, 3 King Beds. Fire pit
Mountain View
9.4 out of 10, Exceptional, (49 reviews)
"Will definitely stay here again!!"
United States
Angela L.
DogOk. Large Retreat, 3 King Beds. Fire pit
Interior

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.
The price is €216
includes taxes & fees
1 Nov - 2 Nov
Adorable Tiny Home │East Side Near Park │Extended Stays Welcome │ Private Home
A wooden cabin with a hot tub, patio furniture, and a covered outdoor area with a grill.

20. 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 €292
includes taxes & fees
1 Nov - 2 Nov
Romantic Guest House on 20 acres - Hot tub, Wildlife, Amazing Pool, Tennis Court
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 Prineville Hotel Reviews

My Place Hotel - Bend, OR

My Place Hotel - Bend, OR

10/10 Excellent
"Great stay. Didn’t use all amenities or need staff services, but it was clean and great location. Thanks"
David 2-night trip
Posted 12 hours ago
My Place Hotel - Bend, OR

Find out more about Prineville

Prineville Holiday Homes information

Number of reviews
593
Accommodation
903 Holiday Homes
Lowest Price
€216
Highest Price
€747