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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester vacation rentals

Exterior detail

1. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 reviews)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
United States
John L.
The price is AED 331
AED 644 total
includes taxes & fees
15 Aug - 16 Aug
Downtown Stay at the Blue Tiny Twin
Terrace/patio

2. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is AED 314
AED 412 total
includes taxes & fees
6 Aug - 7 Aug
Lil Cedar Lodge
Exterior

3. <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, (111 reviews)
"We really enjoyed our stay at April’s house. It was a comfortable house and we loved being so close to Stewart Park for our daily walks."
United States
Sara W.
The price is AED 441
AED 776 total
includes taxes & fees
10 Aug - 11 Aug
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

4. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (26 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is AED 298
AED 607 total
includes taxes & fees
9 Aug - 10 Aug
Downtown Stay at the Red Tiny Twin!
Exterior detail

5. 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, (30 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 AED 404
AED 732 total
includes taxes & fees
23 Aug - 24 Aug
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior

6. 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, (42 reviews)
"Nice place, great location."
United States
Gordon
The price is AED 459
AED 849 total
includes taxes & fees
19 Aug - 20 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Dining

7. 4 BEDROOM House across from River in Best Roseburg area!

4 BEDROOM House across from River in Best Roseburg area!
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"Great stay as always"
United States
Anonymous traveler
The price is AED 459
AED 942 total
includes taxes & fees
24 Aug - 25 Aug
4 BEDROOM House across from River in Best Roseburg area!
Exterior

8. 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, (17 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is AED 397
AED 514 total
includes taxes & fees
10 Aug - 11 Aug
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio

9. 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, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
The price is AED 907
AED 1,138 total
includes taxes & fees
6 Aug - 7 Aug
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Deluxe Apartment, City View | Private kitchen

10. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is AED 1,032
AED 1,412 total
includes taxes & fees
13 Aug - 14 Aug
Bell Sister Flats
Coffee/tea maker, fridge, microwave, oven

11. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
The price is AED 804
AED 1,323 total
includes taxes & fees
13 Aug - 14 Aug
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Dining

12. Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Great property with wonderful views and a quiet relaxing back patio. Large kitchen with a good refrigerator. Very comfortable beds."
United States
Laura O.
Private Umpqua River Retreat w/ 2 King Suites & Patio
Dining

13. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (57 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is AED 595
AED 1,423 total
includes taxes & fees
11 Aug - 12 Aug
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior detail

14. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is AED 878
AED 1,420 total
includes taxes & fees
6 Aug - 7 Aug
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Property grounds

15. Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (47 reviews)
"My visit was very nice and the home owners were very friendly and helpful. I will definitely keep this home in mind for future visits"
United States
Lawrence S.
The price is AED 650
AED 724 total
includes taxes & fees
11 Aug - 12 Aug
Charming, Private Cottage near I-5 and Golf Course.
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 Winchester Hotel Reviews

Holiday Inn Express And Suites Roseburg North By Ihg

Holiday Inn Express And Suites Roseburg North By Ihg

10/10 Excellent
"Great service comfy bed fantastic breakfast quiet room"
Cathleen 1-night trip
Posted less than an hour ago
Holiday Inn Express And Suites Roseburg North By Ihg

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we offer vacation rentals near well known sights in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Winchester is known for its restaurants.

What are some of the best vacation rentals that Winchester has to offer?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath: This vacation home rental near Winchester offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Douglas County Museum of History and Natural History, or get outside and enjoy nature at North Umpqua River. Winchester Dam and Melrose Vineyards are a couple of places you'll find in the larger area.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can book for several days or longer in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.