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Prineville Holiday Rentals

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Our top choices for Prineville holiday rentals

1. Private Ochoco Mountain Cabin Retreat. Five bedrooms 20 minutes from Prineville

Private Ochoco Mountain Cabin Retreat. Five bedrooms 20 minutes from Prineville
Prineville
The price is NZ$873
includes taxes & fees
8 Nov - 9 Nov
Private Ochoco Mountain Cabin Retreat. Five bedrooms 20 minutes from Prineville

2. Crooked River Ranch Cabins

Crooked River Ranch Cabins
3.0 star property
Terrebonne
9.6 out of 10, Exceptional, (381 reviews)
"The place was great and we will be back."
United States
Brian
The price is NZ$147
includes taxes & fees
1 Dec - 2 Dec
Crooked River Ranch Cabins

3. 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.
Spectacular Smith Rock Views on 5 Acres - Quiet and Modern w/ King Beds

4. 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, (56 reviews)
"Great location and amazing property!"
United States
Kim b.
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard

5. 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$371
includes taxes & fees
1 Dec - 2 Dec
Cozy Downtown Redmond Cottage

6. 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.
The price is NZ$413
includes taxes & fees
8 Nov - 9 Nov
Downtown Hub - Dog Friendly

7. Cabin at Brasada Ranch Resort/ 3 Master BD/3.5Ba w/golf course Views & Hot Tub

Cabin at Brasada Ranch Resort/ 3 Master BD/3.5Ba w/golf course Views & Hot Tub
Powell Butte
10.0 out of 10, Exceptional, (19 reviews)
"Perfect location and amenities"
United States
Rainbow S.
The price is NZ$809
includes taxes & fees
8 Nov - 9 Nov
Cabin at Brasada Ranch Resort/ 3 Master BD/3.5Ba w/golf course Views & Hot Tub

8. 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$585
includes taxes & fees
9 Nov - 10 Nov
Romantic Resort Home Private Jacuzzi + Plush Robes

9. Wall Street Suites

Wall Street Suites
3.0 star property
River West
9.8 out of 10, Exceptional, (310 reviews)
"Great! Will come again!"
United States
Wenzhong
The price is NZ$285
includes taxes & fees
30 Nov - 1 Dec
Wall Street Suites

10. King Bed|Non-Smoking

King Bed|Non-Smoking
Madras OR
10.0 out of 10, Exceptional, (47 reviews)
"Felt completely duped by the property description. The staff was nice but the property was not great at all."
United States
Michael S.
The price is NZ$120
includes taxes & fees
18 Nov - 19 Nov
King Bed|Non-Smoking

11. Hillside Loft- Spacious Studio, 100+mbps Wifi, Gas Fireplace, AC, Balcony

Hillside Loft- Spacious Studio, 100+mbps Wifi, Gas Fireplace, AC, Balcony
River West
10.0 out of 10, Exceptional, (32 reviews)
"Great place for two friends to hang out. Quiet, clean, and comfortable. Would stay here again."
United States
Rick F.
The price is NZ$333
includes taxes & fees
8 Nov - 9 Nov
Hillside Loft- Spacious Studio, 100+mbps Wifi, Gas Fireplace, AC, Balcony

12. 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 NZ$441
includes taxes & fees
5 Dec - 6 Dec
Bluebird Day - Ogden Getaway, Cozy 1BR, perfect for couples seeking adventure!

13. Aerie Residences by AvantStay

Aerie Residences by AvantStay
3.0 star property
Summit West
9.8 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay at Aerie Suites by AvantStay. The location is great—close to everything in Bend but still quiet and relaxing. The beds were very comfortable, and the modern finishes made the space feel fresh and welcoming. It was an easy, stress-free place to unwind and made for a perfect, relaxing weekend away."
United States
Lisa
The price is NZ$796
includes taxes & fees
18 Nov - 19 Nov
Aerie Residences by AvantStay

14. 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 NZ$620
includes taxes & fees
9 Nov - 10 Nov
Eagle Crest Desert Sky Retreat - HOT TUB, Dogs OK

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

Spacious downtown pad - billiards/ping pong/sauna
Redmond
9.6 out of 10, Exceptional, (25 reviews)
"Great place to stay. We stayed with our four boys (21,20,18 and15). They enjoyed ping pong and the pool table. Livingroom was nice for relaxing. We would definitely stay again. Host was very responsive. House was very clean and well put together. Beds were comfortable and the house temperature was easy to control."
United States
Anonymous traveller
The price is NZ$964
includes taxes & fees
8 Nov - 9 Nov
Spacious downtown pad - billiards/ping pong/sauna

16. 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.
The price is NZ$675
includes taxes & fees
8 Nov - 9 Nov
Eagle Crest:9th Hole/Priv Hot Tub/Resort Amenities

17. Remodeled cozy cabin on golf course with hot tub!

Remodeled cozy cabin on golf course with hot tub!
Redmond
9.2 out of 10, Wonderful, (144 reviews)
"Was a nice get away! Perfect location to dip in the river or checkOut the caves. Loved the property, and will definitely recommend this place to others!"
United States
Jamie T.
The price is NZ$655
includes taxes & fees
6 Nov - 7 Nov
Remodeled cozy cabin on golf course with hot tub!

18. Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park

Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park
River West
9.8 out of 10, Exceptional, (165 reviews)
"Great location!"
United States
Marc H.
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park

19. Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
Terrebonne
10.0 out of 10, Exceptional, (454 reviews)
"Excellent property and location. The views are incredible. The house is very clean and accommodating. Host was excellent in providing quick replies to any questions I had. Would highly recommend and go back!"
United States
Patrick Q.
The price is NZ$524
includes taxes & fees
16 Nov - 17 Nov
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

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 NZ$547
includes taxes & fees
8 Nov - 9 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

Find out more about Prineville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Prineville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Prineville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Prineville. Seeing all the best attractions is bound to make you fall in love with Prineville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Prineville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Prineville?

Yes, there are holiday rentals close to the most popular sights in Prineville, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Prineville has a good selection of restaurants. Make sure you have time to check out the riverfront and festivals during your trip.

What are some of the best holiday rentals that Prineville has to offer?

HotTub, Near Old Bend & Downtown | Aerie 2BDR King: This holiday home rental outside of Prineville offers a balcony, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Prineville?

Choose from 13 Expedia holiday rentals in Prineville for a memorable holiday.

What can I see and do in Prineville?

Crooked River and Prineville Reservoir State Park are a couple of scenic spots to enjoy the outdoors, whereas A.R. Bowman Museum is one of the cultural attractions. Other places in town to visit include Ochoco National Forest and Ochoco Creek Park.

What are holiday rentals like in Prineville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Prineville. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.