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Roseburg Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Roseburg holiday rentals

A campfire, wooden chairs, and a bench in a forested area with a view of a bridge.

1. Union Creek Resort

Union Creek Resort
3.0 star property
Prospect
8.0 out of 10, Very good, (1,028 reviews)
"Very accommodating & friendly staff."
United States
Dave
The price is S$198
includes taxes & fees
20 Sept - 21 Sept
Union Creek Resort
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

2. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is S$465
includes taxes & fees
26 Aug - 27 Aug
Bell Sister Flats
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

3. 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 S$343
includes taxes & fees
7 Sept - 8 Sept
Starwood Sanctuary
A clear view of a lake with a mountain in the background, a dock, and a chair on a deck.

4. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (472 reviews)
"Great location."
United States
Noni
The price is S$123
includes taxes & fees
9 Sept - 10 Sept
Rocky Point Resort
A covered patio with a hammock chair, outdoor furniture, and a garden area with a stone pathway.

5. Basecamp GP Private Unit in Quiet Duplex

Basecamp GP Private Unit in Quiet Duplex
3.5 star property
Grants Pass
10.0 out of 10, Exceptional, (1 review)
The price is S$226
includes taxes & fees
26 Aug - 27 Aug
Basecamp GP Private Unit in Quiet Duplex
A spacious kitchen with a central island, bar stools, and a fireplace.

6. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is S$533
includes taxes & fees
1 Sept - 2 Sept
Paschal Winery
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

7. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is S$346
includes taxes & fees
31 Aug - 1 Sept
Barclay Klum House by WanderLodges
A covered outdoor seating area with chairs and tables, a fire pit, and a view of a lake.

8. 'crater Lake' Williamson River Resort Cabin 1

'crater Lake' Williamson River Resort Cabin 1
3.0 star property
Chiloquin
10.0 out of 10, Exceptional, (1 review)
"Very cute and cozy cabin by the river. Nothing fancy but comfortable and clean and quiet. Joey is on-site manager and very friendly."
United States
Sarah
The price is S$328
includes taxes & fees
19 Sept - 20 Sept
'crater Lake' Williamson River Resort Cabin 1
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

9. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is S$518
includes taxes & fees
26 Aug - 27 Aug
Savage Upon Siskiyou
A deck with a fire pit, outdoor seating, and a view of the countryside.

10. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is S$501
includes taxes & fees
13 Sept - 14 Sept
Grandview of Ashland
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

11. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is S$494
includes taxes & fees
7 Sept - 8 Sept
The Mountain Ave House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

12. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
The price is S$339
includes taxes & fees
10 Sept - 11 Sept
Hanna's House by WanderLodges
A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

13. The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (6 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is S$507
includes taxes & fees
21 Sept - 22 Sept
The Rellik House and Winery
Two rocking chairs facing a pond with a waterfall, surrounded by lush greenery and wooden fences.

14. A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (52 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
The price is S$316
includes taxes & fees
27 Aug - 28 Aug
A Cowslip's Belle Inn
A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

15. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is S$217
includes taxes & fees
26 Aug - 27 Aug
Rosewood Studio by WanderLodges
An outdoor patio with a stone fireplace, wooden seating, and a view of the surrounding landscape.

16. Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is S$704
includes taxes & fees
7 Sept - 8 Sept
Meadowsweet Farm by WanderLodges
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

17. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is S$604
includes taxes & fees
26 Aug - 27 Aug
Rosewood Collective- House & Studio
A signpost with the word "Canowinga" indicating a location.

18. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is S$279
includes taxes & fees
21 Sept - 22 Sept
Forest Cabin by Crater Lake & Klamath Falls
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

19. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is S$472
includes taxes & fees
26 Aug - 27 Aug
Rosewood Landing- Hot Tub- Sauna
A wooden dock extending into a calm body of water, a green building with a porch, and a 'Welcome' sign.

20. 'crater Lake' Williamson River Resort Cabin 6

'crater Lake' Williamson River Resort Cabin 6
3.0 star property
Chiloquin
10.0 out of 10, Exceptional, (1 review)
"Very nice cabin. We were able to relax and rest. Sitting on the river watching the birds, SO MANY different kinds of birds. It was nice to not have to haul utensils, pots and pans or bedding and towels. It was all ready there. Our dogs went swimming in the river and loved it. Close to Crater Lake, we took a day trip. Clean, quiet, restful. We'll be back."
United States
Brooke
The price is S$431
includes taxes & fees
20 Sept - 21 Sept
'crater Lake' Williamson River Resort Cabin 6
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 Roseburg Hotel Reviews

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"Pleasant and helpful staff. Older well maintained property. Very clean room as well as common areas. The bed was great! Most comfortable nights sleep of my whole road trip. Breakfast was good quality and well monitored by staff. Nothing ran out and the tables and buffet were clean. Our room was huge, more than was expected. Very pleased with this stay all around.:)"
melody 1-night trip
Posted 5 hours ago
Comfort Inn & Suites 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 28 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 Reustle Prayer Rock Vineyards.

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.