Search Holiday Homes in Roseburg

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Roseburg holiday homes

1. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (22 reviews)
"Everything you need is in this small but efficiently planned house. The very small countertop dishwasher is so cute! Perfect place for solo or couple to stay."
United States
Beth B.
The price is £126
includes taxes & fees
1 Dec - 2 Dec
Downtown Stay at the Blue Tiny Twin

2. The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (45 reviews)
"Nice place, great location."
United States
Gordon
The price is £166
includes taxes & fees
13 Nov - 14 Nov
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

3. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (31 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is £118
includes taxes & fees
11 Nov - 12 Nov
Downtown Stay at the Red Tiny Twin!

4. Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (28 reviews)
"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...
United States
Susan
The price is £159
includes taxes & fees
16 Nov - 17 Nov
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

5. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (120 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is £153
includes taxes & fees
13 Nov - 14 Nov
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

6. Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"My friend and I had an amazing stay. We went for a walk, had dinner out on the deck and finished the night drinking wine in the double swing. The stars were amazing. Listen to the owls as we went to sleep. Great place for a get away from the city lights :)"
United States
kimberley
The price is £80
includes taxes & fees
16 Nov - 17 Nov
Tiny House nestled into the Forest on 160 acre Playground.

7. Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (33 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is £136
includes taxes & fees
16 Nov - 17 Nov
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

8. Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
The price is £186
includes taxes & fees
18 Nov - 19 Nov
Starwood Sanctuary

9. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is £262
includes taxes & fees
11 Nov - 12 Nov
The Watusi Place - A Modern Umpqua Valley Getaway

10. Home Sweet Home

Home Sweet Home
Sutherlin
8.8 out of 10, Excellent, (13 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is £249
includes taxes & fees
13 Nov - 14 Nov
Home Sweet Home

11. Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher
Myrtle Creek
10.0 out of 10, Exceptional, (3 reviews)
"The Ranch was everything you could ever want and more it was the most quiet and peaceful night my wife was over the moon with the cows there definitely will be more stays in the future"
United States
Unspecified U.
The price is £163
includes taxes & fees
11 Nov - 12 Nov
Private Ranch House, Highland Cattle, Horses & Peaceful Views - a soul refresher

12. Small house perfect for families and pets

Small house perfect for families and pets
Medford
8.8 out of 10, Excellent, (27 reviews)
"Perfect size for the 4 of us for the weekend."
United States
Anonymous traveller
The price is £157
includes taxes & fees
29 Nov - 30 Nov
Small house perfect for families and pets

13. Skyfall Landing

Skyfall Landing
Eagle Point
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful and comfortable space"
United States
sarah k.
The price is £247
includes taxes & fees
11 Nov - 12 Nov
Skyfall Landing

14. Charming 2BR Cottage • Near Freeway-Cul-de-sac

Charming 2BR Cottage • Near Freeway-Cul-de-sac
Medford
9.2 out of 10, Wonderful, (16 reviews)
"This little house is prefect for a homey, comfort place. The location is great. We will definitely be back"
United States
EmilieC
The price is £150
includes taxes & fees
11 Nov - 12 Nov
Charming 2BR Cottage • Near Freeway-Cul-de-sac

15. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (3 reviews)
"Great little well needed romantic getaway!"
United States
Shawn M.
The price is £134
includes taxes & fees
11 Nov - 12 Nov
Orchard House, Orchard House Retreat

16. Crater Lake Themed Retreat in Eagle Point

Crater Lake Themed Retreat in Eagle Point
Eagle Point
10.0 out of 10, Exceptional, (8 reviews)
"What a beautiful place. Had a great time staying here"
Canada
Hengda
The price is £158
includes taxes & fees
12 Nov - 13 Nov
Crater Lake Themed Retreat in Eagle Point

17. Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-

Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-
Medford
10.0 out of 10, Exceptional, (3 reviews)
"Super convenient location, easy check in and check out. Very comfortable space for 7 girls and we loved having 3 bathrooms to get ready in. Slept great! They also had coffee and creamers provided which was a lovely touch! I would definitely recommend and stay here again!"
United States
Kaci G.
The price is £183
includes taxes & fees
16 Nov - 17 Nov
Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-

18. Great, clean house in the middle of Medford

Great, clean house in the middle of Medford
Medford
9.2 out of 10, Wonderful, (61 reviews)
"The nice size house clean and tidy. Great for everyone who needs their own space."
United States
Lorne D.
The price is £209
includes taxes & fees
11 Nov - 12 Nov
Great, clean house in the middle of Medford

19. The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite

The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite
Shady Cove
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay. Highly recommend!!"
United States
Troy P.
The price is £196
includes taxes & fees
7 Dec - 8 Dec
The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite

20. Creekside Retreat House - Christmas Decoration

Creekside Retreat House - Christmas Decoration
Eagle Point
9.8 out of 10, Exceptional, (6 reviews)
"Great location close to town was very clean peaceful setting with the creek"
United States
jeffery c.
The price is £158
includes taxes & fees
12 Nov - 13 Nov
Creekside Retreat House - Christmas Decoration
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.

Roseburg and related destinations

Nestled along the Umpqua River, this timber town offers world-class fly fishing and nearby wildlife safari adventures. Wineries dot the surrounding valleys, while Crater Lake's stunning blue waters wait just a scenic drive away.

A mountainous landscape with a large lake and a prominent island in the center.