Winchester Vacation Rentals

  • 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

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Winchester vacation rentals

Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,571
￥17,803 total
includes taxes & fees
Apr 6 - Apr 7
Lil Cedar Lodge
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets
Roseburg
10.0 out of 10, Exceptional, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is ￥17,460
￥28,619 total
includes taxes & fees
Apr 2 - Apr 3
A Restful Studio Near a Creek and Forest - Pets
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 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 ￥19,048
￥54,924 total
includes taxes & fees
Apr 4 - Apr 5
Home Sweet Home
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)
"Nice place, great location."
United States
Gordon
The price is ￥19,841
￥35,631 total
includes taxes & fees
Apr 2 - Apr 3
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is ￥18,286
￥25,005 total
includes taxes & fees
Apr 4 - Apr 5
Tiny House nestled into the Forest on 160 acre Playground.
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, (43 reviews)
"Ken & Anya really know how to provide amenities to give warmth and a sense of home. The cottage was simply amazing and we'll be back!"
United States
Robert J.
The price is ￥23,571
￥26,793 total
includes taxes & fees
Apr 6 - Apr 7
Charming, Private Cottage near I-5 and Golf Course.
Smart TV

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Roseburg
9.6 out of 10, Exceptional, (54 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is ￥23,810
￥36,675 total
includes taxes & fees
Apr 2 - Apr 3
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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, (24 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 ￥30,794
￥38,586 total
includes taxes & fees
Apr 6 - Apr 7
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (24 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 ￥13,571
￥27,027 total
includes taxes & fees
Apr 2 - Apr 3
Downtown Stay at the Red Tiny Twin!
Exterior detail

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, (29 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 ￥17,460
￥31,285 total
includes taxes & fees
Apr 2 - Apr 3
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 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 ￥15,079
￥28,679 total
includes taxes & fees
Apr 26 - Apr 27
Downtown Stay at the Blue Tiny Twin
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)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
The price is ￥25,714
￥60,966 total
includes taxes & fees
Apr 4 - Apr 5
The Watusi Place - A Modern Umpqua Valley Getaway
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is ￥43,049
￥59,306 total
includes taxes & fees
Apr 5 - Apr 6
Bell Sister Flats
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
Private bungalow with AC in charming Roseburg
Exterior

Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Glide
The price is ￥60,317
￥105,850 total
includes taxes & fees
Apr 30 - May 1
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
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 ￥37,936
￥59,792 total
includes taxes & fees
May 1 - May 2
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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 ￥34,762
￥56,316 total
includes taxes & fees
May 1 - May 2
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.
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 Winchester Hotel Reviews

The Lodge at Roseburg

The Lodge at Roseburg

10/10 Excellent
"The breakfast was great. Love the hot options. Didn't get to use the pool. There was a large family in it for hours. They definitely sounded like they were having a great time. "
Heather 1-night trip
Posted 5 hours ago
The Lodge at Roseburg

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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?

Singing Waters at N. Umpqua: This Winchester vacation home rental is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease 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.

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. Stewart Park 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.