Book Holiday Homes in Prineville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Prineville

Fantastic home near town, river & hiking with WiFi, deck, enclosed yard & grill

Fantastic home near town, river & hiking with WiFi, deck, enclosed yard & grill

Bend
With a stay at this vacation home in Bend (Southern Crossing), you'll be a 3-minute drive from Old Mill District and 5 minutes from Hayden Homes ...
Fantastic home near town, river & hiking with WiFi, deck, enclosed yard & grill
Sensational Designer's Townhouse in the heart of Eagle Crest.

Sensational Designer's Townhouse in the heart of Eagle Crest.

Redmond
Located in Redmond, this vacation home is within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Sensational Designer's Townhouse in the heart of Eagle Crest.
Historic Belle Millhouse in Bend, OR.  Walk to Downtown.vrbo

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

Bend
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo
Save an average of 15% on thousands of hotels when you're signed in
Riverfront Paradis in Tumalo – Otter Run - Hot Tub, Sauna, Deck, Pet Friendly!

Riverfront Paradis in Tumalo – Otter Run - Hot Tub, Sauna, Deck, Pet Friendly!

Tumalo
With a stay at this vacation home in Bend (Tumalo), you'll be within a 15-minute drive of Old Mill District and Hayden Homes Amphitheater.
Riverfront Paradis in Tumalo – Otter Run - Hot Tub, Sauna, Deck, Pet Friendly!
Eagle Crest Resort Townhome, Pool Access, Nearby Golf, Pickleball, Tennis, Large patio, Fireplace

Eagle Crest Resort Townhome, Pool Access, Nearby Golf, Pickleball, Tennis, Large patio, Fireplace

Redmond
With a stay at this vacation home in Redmond, you'll be within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Eagle Crest Resort Townhome, Pool Access, Nearby Golf, Pickleball, Tennis, Large patio, Fireplace
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

Bend
The price is AU$369 per night from 24 Aug to 25 Aug
AU$369
24 Aug - 25 Aug
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Bend, a 4-minute drive from Old Mill District and 5 minutes from Hayden Homes ...
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
Adorable Bend townhome with ideal location, kitchenette & central AC

Adorable Bend townhome with ideal location, kitchenette & central AC

Bend
The price is AU$265 per night from 18 Aug to 19 Aug
AU$265
18 Aug - 19 Aug
includes taxes & fees
With a stay at this vacation home in Bend (Century West), you'll be a 5-minute drive from Hayden Homes Amphitheater and 6 minutes from Old Mill District.
Adorable Bend townhome with ideal location, kitchenette & central AC
Lodge Vibes in the City - Large Log Home

Lodge Vibes in the City - Large Log Home

Bend
The price is AU$599 per night from 19 Aug to 20 Aug
AU$599
19 Aug - 20 Aug
includes taxes & fees
With a stay at this vacation home in Bend (Mountain View), you'll be within a 15-minute drive of Old Mill District and Hayden Homes Amphitheater.
Lodge Vibes in the City - Large Log Home
MOD POD Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

MOD POD Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

Bend
With a stay at this vacation home in Bend (Larkspur), you'll be within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
MOD POD Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown
Don't see what you're looking for?
See all available properties in Prineville
View all properties
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.

Prineville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Prineville vacation homes are the perfect way for you to wing it.

Holiday houses in Prineville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Prineville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Prineville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Prineville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Prineville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Prineville Holiday Homes essential information

Accommodation
1123 Holiday Homes
Lowest Price
AU$93
Highest Price
AU$599
Popular accommodation
Fantastic home near town, river & hiking with WiFi, deck, enclosed yard & grill, Sensational Designer's Townhouse in the heart of Eagle Crest. , Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo, Riverfront Paradis in Tumalo – Otter Run - Hot Tub, Sauna, Deck, Pet Friendly!, Eagle Crest Resort Townhome, Pool Access, Nearby Golf, Pickleball, Tennis, Large patio, Fireplace, Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby, Adorable Bend townhome with ideal location, kitchenette & central AC, Lodge Vibes in the City - Large Log Home, MOD POD Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

Top trending hotels in Prineville

High Desert Inn

High Desert Inn

2 out of 5
123 NE 3rd Street, Prineville, OR
Fully refundableReserve now, pay when you stay
The price is AU$93 per night from 10 Sept to 11 Sept
AU$93
10 Sept - 11 Sept
includes taxes & fees
With a stay at High Desert Inn in Prineville, you'll be 20.3 mi (32.7 km) from Deschutes County Fairgrounds Expo Center and 23.1 mi (37.1 km) from Smith Rock ...
High Desert Inn
Country Inn & Suites by Radisson, Prineville, OR

Country Inn & Suites by Radisson, Prineville, OR

2.5 out of 5
1773 NE Third Street, Prineville, OR
Fully refundable
The price is AU$278 per night from 17 Aug to 18 Aug
AU$278
17 Aug - 18 Aug
includes taxes & fees
When you stay at Country Inn & Suites by Radisson, Prineville, OR in Prineville, you'll be in the business district, within a 5-minute drive of Ochoco Creek ...
Country Inn & Suites by Radisson, Prineville, OR
Best Western Prineville Inn

Best Western Prineville Inn

2.5 out of 5
1475 NE 3rd Street, Prineville, OR
Fully refundableReserve now, pay when you stay
The price is AU$280 per night from 13 Aug to 14 Aug
AU$280
13 Aug - 14 Aug
includes taxes & fees
Located in Prineville, Best Western Prineville Inn is within a 5-minute drive of Ochoco Creek Park and A.R. Bowman Museum.
Best Western Prineville Inn
Save an average of 15% on thousands of hotels when you're signed in
Riverhouse Lodge

Riverhouse Lodge

3.5 out of 5
3075 N. Business 97, Bend, OR
Fully refundableReserve now, pay when you stay
The price is AU$377 per night from 24 Aug to 25 Aug
AU$377
24 Aug - 25 Aug
includes taxes & fees
In the heart of Bend, Riverhouse Lodge is within a 5-minute drive of Blockbuster and River's Edge Golf Course.
Riverhouse Lodge
Don't see what you're looking for?
See all available properties in Prineville
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.