Search Holiday Rentals in Roseburg

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Holiday Rentals in Roseburg

Property grounds
Crater Lake Resort

Cabin in Chiloquin

3.0 star property
8.4 out of 10, Very good, (518)
"Great place near crater lake "
United States
Lori
Crater Lake Resort
Sun deck
Rocky Point Resort

Cabin in Klamath Falls

2.5 star property
8.2 out of 10, Very good, (402)
"Had a wonderful stay..!! Would love to stay again."
United States
NAGA HALINI
The price is 2.254.037 ₫
2.558.266 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Rocky Point Resort
Hiking
Union Creek Resort

Cabin in Prospect

3.0 star property
8.0 out of 10, Very good, (911)
"Clean, rustic, and good front desk personnel. "
United States
Charlotte
Union Creek Resort
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace
Paschal Winery

Cottage in Talent

4.5 star property
9.6 out of 10, Exceptional, (14)
"Very nice and hassle free check in "
United States
Matthew
The price is 3.369.064 ₫
5.923.989 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Paschal Winery
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels
The Rellik House and Winery

Holiday Home in Central Point

3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is 4.297.169 ₫
6.866.111 ₫ total
includes taxes & fees
10 Dec - 11 Dec
The Rellik House and Winery
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels
Rosewood Studio by WanderLodges

Holiday Home in Medford

3.0 star property
The price is 3.295.250 ₫
4.893.447 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Rosewood Studio by WanderLodges
Apartment | 6 bedrooms
Medford Home and 2 Condos With Pool and Hot tub

Aparthotel in Medford

2.0 star property
The price is 2.119.374 ₫
5.690.402 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Medford Home and 2 Condos With Pool and Hot tub
Family House, Kitchen, Garden View | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Lanka Rose House by WanderLodges

Holiday Home in Phoenix

3.5 star property
10.0 out of 10, Exceptional, (1)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is 2.989.451 ₫
6.557.010 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Lanka Rose House by WanderLodges
House | 3 bedrooms
Enchanting Getaway: Farmhouse and Tiny House Duo

Aparthotel in Jacksonville

2.0 star property
The price is 2.181.454 ₫
5.922.218 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Enchanting Getaway: Farmhouse and Tiny House Duo
Terrace/patio
Grandview of Ashland

Holiday Home in Ashland

3.0 star property
10.0 out of 10, Exceptional, (2)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
United States
Monica
The price is 5.310.299 ₫
10.901.705 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Grandview of Ashland
Apartment (0 Bedroom) | Interior
Riverfront Resort Cabin ~ 21 Mi to Crater Lake!

Apartment in Chiloquin

3.0 star property
9.0 out of 10, Wonderful, (2)
"Great location right on the Williamson River. Quiet and recently re-done tiny cabin. A little quirky, but very nice “kitchen”. "
United States
Maria
The price is 4.033.386 ₫
7.859.567 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Riverfront Resort Cabin ~ 21 Mi to Crater Lake!
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Barclay Klum House by WanderLodges

Holiday Home in Ashland

4.0 star property
10.0 out of 10, Exceptional, (6)
"Great ~ memorable stay. "
United States
Melissa
The price is 3.250.435 ₫
6.985.593 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Barclay Klum House by WanderLodges
Main House | Terrace/patio
A Cowslip's Belle Inn

Apartment in Ashland

3.0 star property
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is 3.558.870 ₫
5.437.822 ₫ total
includes taxes & fees
10 Dec - 11 Dec
A Cowslip's Belle Inn
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster
Hanna's House by WanderLodges

Holiday Home in Historic Railroad District

4.0 star property
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is 3.110.571 ₫
5.442.863 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hanna's House by WanderLodges
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Roseburg Hotel Reviews

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"It was all good! "
Doug 1-night trip
Posted 2 days ago
Flagship Inn of Ashland

Frequently asked questions

Can I find holiday rentals in Roseburg?

Yes, there are holiday rentals in Roseburg close to Douglas County Museum of History and Natural History, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Roseburg speak positively about the scenic riverfront and top-notch restaurants in this destination. Make sure you have time to check out the live music while you're in the area.

How many holiday rentals will I find in Roseburg?

With 35 Expedia holiday rentals, you're guaranteed to find just the right place for your Roseburg stay.

What’s there to see and do in Roseburg?

Winchester Dam and South Umpqua River are a couple of scenic spots to enjoy the outdoors, whereas Douglas County Museum of History and Natural History is one of the cultural attractions. Other places in town to visit include Melrose Vineyards and HillCrest Winery and Distillery.

What’s a holiday rental in Roseburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roseburg. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.