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Eastern Oregon Holiday Rentals

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Our top choices for Eastern Oregon holiday rentals

1. Palmer House, Studio 3, Cozy Studio for 2 Downtown! Local Golfing 50% Off!

Palmer House, Studio 3, Cozy Studio for 2 Downtown! Local Golfing 50% Off!
Baker City
9.6 out of 10, Exceptional, (41 reviews)
"Very clean, quiet and beautiful back yard to hang out in at night. Loved this place."
United States
Tanya B.
The price is NZ$219
includes taxes & fees
13 Nov - 14 Nov
Palmer House, Studio 3, Cozy Studio for 2 Downtown! Local Golfing 50% Off!

2. Cozy Cabin with River Access optional full 50amp RV hook-ups onsite

Cozy Cabin with River Access optional full 50amp RV hook-ups onsite
Kimberly
9.6 out of 10, Exceptional, (24 reviews)
"Lovely quiet property on a working farm, well-stocked although needs USB, USB-C etc charging ports. Active but friendly dogs, so if you do not like dogs, maybe not the place for you; I enjoyed them. It was the perfect spot to explore the John Day National Monument area, and the view from the front porch was lovely."
United States
Jeanne
The price is NZ$517
includes taxes & fees
23 Nov - 24 Nov
Cozy Cabin with River Access optional full 50amp RV hook-ups onsite

3. Downtown Retreat - Cozy Getaway! Studio for 2, Local Golfing 50% Off!

Downtown Retreat - Cozy Getaway! Studio for 2, Local Golfing 50% Off!
Baker City
9.8 out of 10, Exceptional, (40 reviews)
"There was freshly baked bread waiting for me in a Zojirushi bread baker! Lovely touch! The layout of the property was super: very efficient, yet plenty of room. I would definitely stay here again."
United States
Anita
The price is NZ$337
includes taxes & fees
12 Nov - 13 Nov
Downtown Retreat - Cozy Getaway! Studio for 2, Local Golfing 50% Off!

4. Cozy apartment near downtown Prairie City.

Cozy apartment near downtown Prairie City.
Prairie City
10.0 out of 10, Exceptional, (6 reviews)
"Perfect base from which to enjoy Prairie City and the surrounding area."
United States
Robert K.
The price is NZ$564
includes taxes & fees
15 Nov - 16 Nov
Cozy apartment near downtown Prairie City.

5. 3rd Street Stop-cottage house,walking distance to middle of town and activities

3rd Street Stop-cottage house,walking distance to middle of town and activities
Baker City
9.8 out of 10, Exceptional, (51 reviews)
"A cute and quiet spot with easy walking access to nearby restaurants and attractions. "
United States
Matthew A.
The price is NZ$279
includes taxes & fees
21 Nov - 22 Nov
3rd Street Stop-cottage house,walking distance to middle of town and activities

6. Scenic Views Casita 2 - Cozy Studio for 2, Local Golfing 50% Off!

Scenic Views Casita 2 - Cozy Studio for 2, Local Golfing 50% Off!
Baker City
10.0 out of 10, Exceptional, (12 reviews)
"Great location and super cozy!"
United States
Dru Van
The price is NZ$277
includes taxes & fees
12 Nov - 13 Nov
Scenic Views Casita 2 - Cozy Studio for 2, Local Golfing 50% Off!

7. Claim Jumpers Cottage, Sleeps 4 w/ Sauna! Local Golfing 50% Off!

Claim Jumpers Cottage, Sleeps 4 w/ Sauna! Local Golfing 50% Off!
Baker City
10.0 out of 10, Exceptional, (63 reviews)
"Very comfortable place. Great features such as a sons, the back yard amenities, such as smoker, barbecue and plenty of places to sit. Although it was a short day, really enjoyed it."
United States
Tanya B.
The price is NZ$314
includes taxes & fees
12 Nov - 13 Nov
Claim Jumpers Cottage, Sleeps 4 w/ Sauna! Local Golfing 50% Off!

8. Grove Street Couplet #1

Grove Street Couplet #1
Baker City
10.0 out of 10, Exceptional, (6 reviews)
"Would stay again"
United States
Joel C.
The price is NZ$370
includes taxes & fees
16 Nov - 17 Nov
Grove Street Couplet #1

9. Baby Bear’s Playhouse

Baby Bear’s Playhouse
Burns
9.8 out of 10, Exceptional, (21 reviews)
"The place is easy to get to, clean, air conditioned, we didn’t have our dog this time but when we stayed before we did. We have stayed in mama bear cabin and this time baby bear, both are great."
United States
Jo D.
The price is NZ$223
includes taxes & fees
20 Nov - 21 Nov
Baby Bear’s Playhouse

10. East Empire Theatre Loft, Downtown! Sleeps 4, Local Golfing 50% Off!

East Empire Theatre Loft, Downtown! Sleeps 4, Local Golfing 50% Off!
Baker City
10.0 out of 10, Exceptional, (92 reviews)
"It was a beuatiful property. Host was great. Loved Baker City and being right on Main. My family had such a wonderful stay."
United States
Leslie U.
The price is NZ$414
includes taxes & fees
12 Nov - 13 Nov
East Empire Theatre Loft, Downtown! Sleeps 4, Local Golfing 50% Off!

11. EVERYTHING IS NEW! Adorable Tiny Log Cabin with Awesome Views, Walk Everywhere

EVERYTHING IS NEW! Adorable Tiny Log Cabin with Awesome Views, Walk Everywhere
Joseph
9.8 out of 10, Exceptional, (9 reviews)
"Great little cabin walking distance to restaurants and bars in Joseph."
United States
Kevan G.
The price is NZ$480
includes taxes & fees
12 Nov - 13 Nov
EVERYTHING IS NEW! Adorable Tiny Log Cabin with Awesome Views, Walk Everywhere

12. Studio with so much to offer! Small family and pet friendly.

Studio with so much to offer! Small family and pet friendly.
Payette
10.0 out of 10, Exceptional, (65 reviews)
"Nice stay"
United States
Michelle
The price is NZ$318
includes taxes & fees
15 Nov - 16 Nov
Studio with so much to offer! Small family and pet friendly.

13. Lone Wolf Lodge - in Wallowa-Whitman Nat`l Forest

Lone Wolf Lodge - in Wallowa-Whitman Nat`l Forest
Baker City
9.8 out of 10, Exceptional, (33 reviews)
"Very beautiful place to stay! Wish I had planned more time at this destination! Peaceful and beauty all around inside and out!"
United States
Tammy C.
The price is NZ$610
includes taxes & fees
12 Nov - 13 Nov
Lone Wolf Lodge - in Wallowa-Whitman Nat`l Forest

14. Mama Bear’s Den- Pet Friendly

Mama Bear’s Den- Pet Friendly
Burns
10.0 out of 10, Exceptional, (73 reviews)
"Great stay. Very quaint place."
United States
Ann L.
The price is NZ$268
includes taxes & fees
28 Nov - 29 Nov
Mama Bear’s Den- Pet Friendly

15. The Cozy Nest Vacation

The Cozy Nest Vacation
Burns
9.6 out of 10, Exceptional, (48 reviews)
"This is a quaint cozy and comfortable place to stay."
United States
Bruce G.
The price is NZ$274
includes taxes & fees
20 Nov - 21 Nov
The Cozy Nest Vacation

16. 1930 Bungalow near downtown Weiser

1930 Bungalow near downtown Weiser
Weiser
8.8 out of 10, Excellent, (40 reviews)
"Great place, exactly as advertised. It was a good value. Would stay again."
United States
Richard L.
The price is NZ$297
includes taxes & fees
2 Dec - 3 Dec
1930 Bungalow near downtown Weiser

17. River Front Cabin. Come relax and play cowboy in Spray !

River Front Cabin. Come relax and play cowboy in Spray !
Spray
10.0 out of 10, Exceptional, (6 reviews)
"Loved this placed. We saw deer, cows, turkey, geese, stars, and beautiful cloud formations just from the back deck. The interior is very comfortable and spotlessly clean. Our family had a great time and we'd love to return. "
United States
amanda z.
The price is NZ$1,284
includes taxes & fees
24 Nov - 25 Nov
River Front Cabin. Come relax and play cowboy in Spray !

18. Palmer`s Ski Shack, Cozy studio for 2!

Palmer`s Ski Shack, Cozy studio for 2!
Baker City
10.0 out of 10, Exceptional, (3 reviews)
"Quiet, great place to stay. Highly recommended. "
United States
Kate R.
The price is NZ$356
includes taxes & fees
10 Dec - 11 Dec
Palmer`s Ski Shack, Cozy studio for 2!

19. Family Sized Cozy Retreat located right next to the Famous Haines Steakhouse!

Family Sized Cozy Retreat located right next to the Famous Haines Steakhouse!
Haines
The price is NZ$345
includes taxes & fees
12 Nov - 13 Nov
Family Sized Cozy Retreat located right next to the Famous Haines Steakhouse!

20. The Little Modern, Mid-Century Stay near the Path, 2 bdrm, 1 bath

The Little Modern, Mid-Century Stay near the Path, 2 bdrm, 1 bath
Baker City
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, clean, comfortable and very thoughtful hosts."
United States
Manuel R.
The Little Modern, Mid-Century Stay near the Path, 2 bdrm, 1 bath
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 Eastern Oregon Hotel Reviews

Find out more about Eastern Oregon

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 Eastern Oregon 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 Eastern Oregon. 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 Eastern Oregon. Seeing all the best attractions is bound to make you fall in love with Eastern Oregon. 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 Eastern Oregon short-term rentals, that won’t be hard to do.