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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winchester vacation rentals

Terrace/patio

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 ￥12,979
￥17,240 total
includes taxes & fees
Jun 16 - Jun 17
Lil Cedar Lodge
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (20 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 ￥15,223
￥28,952 total
includes taxes & fees
Jun 16 - Jun 17
Downtown Stay at the Blue Tiny Twin
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.8 out of 10, Excellent, (11 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 ￥19,229
￥56,148 total
includes taxes & fees
Jun 16 - Jun 17
Home Sweet Home
Deluxe Apartment, City View | Bathroom

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is ￥46,490
￥63,189 total
includes taxes & fees
Jun 16 - Jun 17
Bell Sister Flats
Exterior

<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, (99 reviews)
"The Keasington house was perfect for our trip to see family. It had everything we needed. Will definitely be staying again next time we are in the area!"
United States
Michelle C.
The price is ￥19,229
￥33,689 total
includes taxes & fees
Jun 29 - Jun 30
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

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)
"Awesome place!"
United States
McKay J.
The price is ￥21,200
￥26,397 total
includes taxes & fees
Jun 16 - Jun 17
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

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, (39 reviews)
"April‘s place is comfortable, clean, a great location and we have stayed several times. She’s easy to communicate with and I’ll back again next month and in the future again."
United States
Thomas J.
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds

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, (45 reviews)
"We had one night and loved the cottage. We will definitely stay again next time we are in town. The cottage is beautifully built and has amazing landscape and scenery surrounding it. Myrtle Creek is a hidden gem."
United States
Jessica S.
The price is ￥27,369
￥30,622 total
includes taxes & fees
Jun 16 - Jun 17
Charming, Private Cottage near I-5 and Golf Course.
Terrace/patio

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)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is ￥39,579
￥49,482 total
includes taxes & fees
Jun 16 - Jun 17
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is ￥38,297
￥61,939 total
includes taxes & fees
Jun 16 - Jun 17
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (51 reviews)
"Good hosts & very nice home."
United States
Pamela M.
The price is ￥28,843
￥65,371 total
includes taxes & fees
Jul 14 - Jul 15
The Watusi Place - A Modern Umpqua Valley Getaway
Fridge, microwave, oven, stovetop

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)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is ￥35,093
￥58,079 total
includes taxes & fees
Jun 16 - Jun 17
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

8/10 Good
"Good for the price."
mark 1-night trip
Posted less than an hour ago
Motel 6 Sutherlin, OR

Find out more about Winchester

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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?

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun: This vacation home rental near Winchester offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Wildlife Safari, or get outside and enjoy nature at North Umpqua River. Winchester Dam and Stewart Park 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.