Holiday Homes in Prineville

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Prineville

Our top choices for Prineville holiday homes

Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
Outdoor spa tub

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

10.0 out of 10, Exceptional, (401)
"This is one of our favorite place to go for all occasions!"
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
Cozy knotty pine chalet with creekside deck, BBQ, and access to pools, hot tubs, gym, golf, hiking.
Interior

Cozy knotty pine chalet with creekside deck, BBQ, and access to pools, hot tubs, gym, golf, hiking.

10.0 out of 10, Exceptional, (76)
"Love staying in this location"
The price is AU$612
includes taxes & fees
15 Sept - 16 Sept
Cozy knotty pine chalet with creekside deck, BBQ, and access to pools, hot tubs, gym, golf, hiking.
Drake Park Cottage
TV, fireplace

Drake Park Cottage

9.8 out of 10, Exceptional, (165)
"Private, clean, and newly remodeled. We always love staying here in this great location near Drake Park."
The price is AU$683
includes taxes & fees
2 Sept - 3 Sept
Drake Park Cottage
Historic Craftsman Bungalow, Just Steps to Downtown ~HOT TUB!~
Outdoor dining

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

10.0 out of 10, Exceptional, (203)
"The location is amazing and the house is wonderful. Definitely recommend to any one looking for a nice spot in walking distance of downtown Bend."
The price is AU$965
includes taxes & fees
26 Sept - 27 Sept
Historic Craftsman Bungalow, Just Steps to Downtown ~HOT TUB!~
Walk to downtown and Amphitheater
Exterior

Walk to downtown and Amphitheater

4.0 star property
9.2 out of 10, Wonderful, (28)
"Our stay was the first time in Bend, so the location was perfect. It was easy to get anywhere and within walking distance to many restaurants and park. The house itself is small, with a small enclosed front yard, which is great if you have a dog. My husband was worried about the Wi-Fi speed because he had to work remotely. But that worked fine as well and we could all connect without any issue. Our only suggestion is that someone check the utensils and trash bags between guests. We only found...
Walk to downtown and Amphitheater
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Terrace/patio

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

10.0 out of 10, Exceptional, (33)
"Nice house in a great location as long as you want to be downtown. Perfect for walkability, with food options all around."
The price is AU$360
includes taxes & fees
2 Sept - 3 Sept
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
King bed - Pet Friendly - Jameson's Place
Exterior

King bed - Pet Friendly - Jameson's Place

9.6 out of 10, Exceptional, (43)
"Very clean, great kitchen, huge master and great location."
The price is AU$481
includes taxes & fees
1 Sept - 2 Sept
King bed - Pet Friendly - Jameson's Place
Gather! A Welcoming Home - King Beds - Pool Table!
Fridge, microwave, oven, stovetop

Gather! A Welcoming Home - King Beds - Pool Table!

10.0 out of 10, Exceptional, (15)
"The young people in our group enjoyed the pool table, and I appreciated the fact that the kitchen was well stocked with appliances and utensils."
The price is AU$473
includes taxes & fees
3 Sept - 4 Sept
Gather! A Welcoming Home - King Beds - Pool Table!
Private Hot Tub! Beautiful Townhome at Eagle Crest - Remodeled ~ Fireplace
Interior

Private Hot Tub! Beautiful Townhome at Eagle Crest - Remodeled ~ Fireplace

9.8 out of 10, Exceptional, (72)
"Great stay - just as described"
The price is AU$870
includes taxes & fees
2 Sept - 3 Sept
Private Hot Tub! Beautiful Townhome at Eagle Crest - Remodeled ~ Fireplace
Cute, Quiet & Private Bungalow - Newly Remodeled
TV, fireplace

Cute, Quiet & Private Bungalow - Newly Remodeled

10.0 out of 10, Exceptional, (15)
"This was a wonderful private spot for my trip to spend time with family in the area. I appreciated the communication, I will definitely stay again!"
The price is AU$329
includes taxes & fees
3 Sept - 4 Sept
Cute, Quiet & Private Bungalow - Newly Remodeled
Hot Tub ~ Westside Bend Home ~ AC ~ Fireplace ~ EV charger
Exterior

Hot Tub ~ Westside Bend Home ~ AC ~ Fireplace ~ EV charger

9.8 out of 10, Exceptional, (43)
"The house was fantastic, perfect for our family of 4. We’re in bend every year and this is our favorite neighborhood, walkable to great restaurants and close to lots of outdoor activities "
The price is AU$940
includes taxes & fees
3 Sept - 4 Sept
Hot Tub ~ Westside Bend Home ~ AC ~ Fireplace ~ EV charger
DogOk. Large Retreat, 3 King Beds. Fire pit
Terrace/patio

DogOk. Large Retreat, 3 King Beds. Fire pit

9.4 out of 10, Exceptional, (43)
"We stayed here as a family and with friends while down in Bend for a baseball tournament. The house is awesome and super spacious. Everywhere in Bend is just a few minutes away and there's a grocery store around the corner. We'll be back!"
The price is AU$700
includes taxes & fees
2 Sept - 3 Sept
DogOk. Large Retreat, 3 King Beds. Fire pit
Comfortable condo with private hot tub & tennis-great location
Outdoor dining

Comfortable condo with private hot tub & tennis-great location

9.0 out of 10, Wonderful, (82)
"Perfect spot for 2. Easy access to anything in town. Loved it!! "
The price is AU$465
includes taxes & fees
1 Sept - 2 Sept
Comfortable condo with private hot tub & tennis-great location
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
Terrace/patio

Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba

9.6 out of 10, Exceptional, (61)
"We stayed for a baseball tournament. It was clean and a great location for having to go to multiple fields "
The price is AU$532
includes taxes & fees
1 Sept - 2 Sept
Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
1 bedroom, WiFi, bed sheets

Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard

10.0 out of 10, Exceptional, (35)
"Location was very convenient to downtown Redmond. Was great having a garage to park in and house was very well kept and clean."
The price is AU$440
includes taxes & fees
1 Sept - 2 Sept
Impeccable Guest House, New Furnishing, Near Downtown. EV Charger, Dog Friendly, Deck, Enclosed Yard
Hot Tub ~ Fireplace ~ Brand New Furnishings ~ Dog Friendly
Fridge, microwave, oven, stovetop

Hot Tub ~ Fireplace ~ Brand New Furnishings ~ Dog Friendly

10.0 out of 10, Exceptional, (36)
"We loved staying at this very comfortable rental in Bend. It was convenient to everywhere we wanted to go. We’d recommend it to others. "
The price is AU$979
includes taxes & fees
3 Sept - 4 Sept
Hot Tub ~ Fireplace ~ Brand New Furnishings ~ Dog Friendly
King Bed - Pet Friendly - EV Charger - Emersen’s Place
Fridge, microwave, oven, stovetop

King Bed - Pet Friendly - EV Charger - Emersen’s Place

9.8 out of 10, Exceptional, (26)
"Good location, super communicative host!"
The price is AU$481
includes taxes & fees
7 Sept - 8 Sept
King Bed - Pet Friendly - EV Charger - Emersen’s Place
The Quails Nest! SW Bend Custom Family Friendly Home ~ Fire pit ~ Pac Man
Fridge, microwave, oven, stovetop

The Quails Nest! SW Bend Custom Family Friendly Home ~ Fire pit ~ Pac Man

9.8 out of 10, Exceptional, (48)
"Fun spot in Bend. Great access to the mountain. "
The price is AU$779
includes taxes & fees
3 Sept - 4 Sept
The Quails Nest! SW Bend Custom Family Friendly Home ~ Fire pit ~ Pac Man
Spectacular Smith Rock Views on Property - Quiet and Modern w/ King Beds
Interior

Spectacular Smith Rock Views on Property - Quiet and Modern w/ King Beds

10.0 out of 10, Exceptional, (7)
"Amazing views were the best part, of course! Owners communicated with us well and we felt taken care of! We had a great stay! "
The price is AU$468
includes taxes & fees
7 Sept - 8 Sept
Spectacular Smith Rock Views on Property - Quiet and Modern w/ King Beds
Modern home in Bend! Close to Shopping & Food Carts ~ Pet Friendly!
Fridge, microwave, oven, stovetop

Modern home in Bend! Close to Shopping & Food Carts ~ Pet Friendly!

9.8 out of 10, Exceptional, (34)
"Nice house and room for us, our adult children, my parents, and our small dog. Had many great adventures and would stay here again!"
Modern home in Bend! Close to Shopping & Food Carts ~ Pet Friendly!
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
Sign in
Sign up, it's free

Top Prineville Hotel Reviews

Find out more about Prineville

Find out more about Prineville

Prineville Holiday Homes information

Number of reviews
Accommodation
1136 Holiday Homes
Lowest Price
AU$255
Highest Price
AU$572

Explore a world of travel with Expedia

Explore a world of travel with Expedia