A large, layered mountain with distinct geological formations.

Holiday Homes in Prineville

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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 Prineville holiday homes

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

1. 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$538
includes taxes & fees
26 Oct - 27 Oct
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
A modern living room with a sofa, armchair, and dining area, featuring large windows and a view of a mountainous landscape.

2. 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 NZ$477
includes taxes & fees
4 Nov - 5 Nov
Spectacular Smith Rock Views on 5 Acres - Quiet and Modern w/ King Beds
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.
The price is NZ$350
includes taxes & fees
28 Oct - 29 Oct
Cozy Downtown Redmond Cottage
A large wooden barn-style sliding door in a room with light-colored wooden flooring and a blue curtain.

4. Downtown Hub - Dog Friendly

Downtown Hub - Dog Friendly
Redmond
10.0 out of 10, Exceptional, (72 reviews)
"Great house great place to stay! "
United States
Matt w.
The price is NZ$422
includes taxes & fees
30 Oct - 31 Oct
Downtown Hub - Dog Friendly
A living room with a fireplace, a television, a sofa, and a coffee table.

5. 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 NZ$481
includes taxes & fees
9 Nov - 10 Nov
Romantic Resort Home Private Jacuzzi + Plush Robes
A modern building with an outdoor seating area featuring Adirondack chairs and a fire pit.

6. 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 NZ$1,086
includes taxes & fees
28 Oct - 29 Oct
Private Retreat Steps to Smith Rock | Quiet Luxury & Hot Tub
A modern kitchen with a central island, pendant lighting, and white cabinets.

7. 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
The price is NZ$993
includes taxes & fees
2 Nov - 3 Nov
Spacious downtown pad - billiards/ping pong/sauna
A hotel with a swimming pool, a covered patio, and a well-maintained lawn.

8. Updated Eagle Crest Townhouse with resort amenities. Family friendly. Pond view!

Updated Eagle Crest Townhouse with resort amenities. Family friendly. Pond view!
Redmond
9.4 out of 10, Exceptional, (18 reviews)
"Great stay, communication, and overall experience!"
United States
Joe D.
The price is NZ$622
includes taxes & fees
30 Oct - 31 Oct
Updated Eagle Crest Townhouse with resort amenities. Family friendly. Pond view!
A spacious living room with a fireplace, a large clock, and a balcony with outdoor furniture.

9. 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 NZ$857
includes taxes & fees
21 Nov - 22 Nov
Charming 3-bedroom townhome with WiFi, fitness room in peaceful Redmond
A single-story house with a front porch, a garage, and a well-maintained lawn.

10. 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.
Eagle Crest Desert Sky Retreat - HOT TUB, Dogs OK
A spacious living area with a leather sofa, a dining table, and a bar area with stools.

11. 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, (5 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 NZ$639
includes taxes & fees
9 Nov - 10 Nov
Eagle Crest Retreat on Golf course, Private w/View
A wooden deck with outdoor furniture, overlooking a grassy area with trees and a clear sky.

12. 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.
The price is NZ$693
includes taxes & fees
9 Nov - 10 Nov
Eagle Crest Hole in One!
A modern two-story house with a stone foundation, a garage, and a landscaped yard.

13. 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.
The price is NZ$875
includes taxes & fees
24 Oct - 25 Oct
Eagle Crest Retreat | 6 Resort Passes Included
An indoor swimming pool with a wooden ceiling and large windows.

14. Eagle Crest: Resort Amenities-Spa-9th Hole-Views!

Eagle Crest: Resort Amenities-Spa-9th Hole-Views!
Deschutes County
9.8 out of 10, Exceptional, (55 reviews)
"Loved the location! Very clean & comfortable."
United States
Julie K.
The price is NZ$719
includes taxes & fees
2 Nov - 3 Nov
Eagle Crest: Resort Amenities-Spa-9th Hole-Views!
Pool

15. 3 BR Pet-Friendly Townhouse @ Juniper Preserve Resort

3 BR Pet-Friendly Townhouse @ Juniper Preserve Resort
Pronghorn
3 BR Pet-Friendly Townhouse @ Juniper Preserve Resort
Pool

16. Upscale 3 BR Townhouse @ Juniper Preserve Resort

Upscale 3 BR Townhouse @ Juniper Preserve Resort
Pronghorn
The price is NZ$1,704
includes taxes & fees
21 Nov - 22 Nov
Upscale 3 BR Townhouse @ Juniper Preserve Resort
A two-story house with a balcony, a garage, and a covered outdoor area.

17. 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, (3 reviews)
"Very clean and tastefully updated. Location was great for our needs and very quiet."
United States
Thom S.
The price is NZ$417
includes taxes & fees
9 Nov - 10 Nov
New Listing! Dog Friendly, Mountain-Modern Retreat in Bend. Property with views
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.

18. 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$317
includes taxes & fees
25 Oct - 26 Oct
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
A spacious log cabin interior with a wooden floor, a leather sofa, a dining area, and a kitchen.

19. 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 NZ$565
includes taxes & fees
25 Oct - 26 Oct
Lodge Vibes in the City - Large Log Home
Pool

20. Upscale 4 BR Townhouse @ Juniper Preserve Resort

Upscale 4 BR Townhouse @ Juniper Preserve Resort
Pronghorn
The price is NZ$1,723
includes taxes & fees
2 Nov - 3 Nov
Upscale 4 BR Townhouse @ Juniper Preserve Resort
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
"Nice property Close to downtown which we needed. Will stay again"
James 2-night trip
Posted 7 hours ago
My Place Hotel - Bend, OR

Find out more about Prineville

Prineville Holiday Homes information

Number of reviews
466
Accommodation
985 Holiday Homes
Lowest Price
NZ$317
Highest Price
NZ$1,723