Winchester Vacation Rentals

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Vacation Rentals in Winchester

Interior
Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
10.0 out of 10, Exceptional, (8)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
United States
Joanna D.
Singing Waters at N. Umpqua
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North
9.4 out of 10, Exceptional, (16)
"great property"
United States
Mai
$441 nightly
The price is $448
Nov 19 - Nov 20
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop
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, (51)
"It was a great place, super close proximity to grocery stores and the airport which is where I needed to be each day for work. "
United States
Dana M.
$183 nightly
The price is $200
Nov 19 - Nov 20
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior
Heavenly Bungalow, immaculately clean, close to downtown!

Heavenly Bungalow, immaculately clean, close to downtown!

Roseburg
10.0 out of 10, Exceptional, (48)
"Nice place to stay. "
United States
Janine
Heavenly Bungalow, immaculately clean, close to downtown!
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, (12)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
$155 nightly
The price is $158
Nov 28 - Nov 29
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
Exterior detail
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Roseburg
10.0 out of 10, Exceptional, (75)
"Another great stay!This is my second year staying at this property. It is located in a very quiet neighborhood. The home is kept very clean and is well stocked. We hope to be back next year!Thanks!"
United States
Susan B.
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
Fridge, microwave, oven, stovetop
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Roseburg
9.8 out of 10, Exceptional, (36)
"This place is great. We have stayed multiple times. Will continue to come back here when in the area. "
United States
Benjamin B.
$286 nightly
The price is $313
Nov 25 - Nov 26
Total with taxes and fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop
Family home

Family home

Roseburg
9.8 out of 10, Exceptional, (8)
"I would suggest to everyone to stay here!"
United States
Kendal M.
Family home
Interior
<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, (89)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
$198 nightly
The price is $217
Nov 19 - Nov 20
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Outdoor dining
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Roseburg
9.4 out of 10, Exceptional, (24)
"It was nice."
United States
Al N.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Property entrance
River Vista Vacation Homes

River Vista Vacation Homes

3.0 star property
Idleyld Park
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
United States
Emily
River Vista Vacation Homes
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, (40)
"Extremely comfortable! Beautiful accommodations. "
United States
Ruby G.
$183 nightly
The price is $183
Nov 25 - Nov 26
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
10.0 out of 10, Exceptional, (46)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
$337 nightly
The price is $365
Nov 19 - Nov 20
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Property grounds
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

Idleyld Park
9.8 out of 10, Exceptional, (57)
"great nature location, the river was fun to swim at "
United States
Ami S.
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
House (1 Bedroom) | Interior
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
Oakland
10.0 out of 10, Exceptional, (1)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
United States
Wayne
Southern Oregon Cabin: Fire Pit & Private Pond!
1 bedroom, bed sheets
Lil Cedar Lodge

Lil Cedar Lodge

Roseburg
$111 nightly
The price is $112
Nov 24 - Nov 25
Total with taxes and fees
Lil Cedar Lodge
Fridge, microwave, oven, stovetop
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston
9.6 out of 10, Exceptional, (60)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
United States
Gina C.
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Property grounds
the Bunkhouse coyote- Private Studio Retreat Room

the Bunkhouse coyote- Private Studio Retreat Room

2.0 star property
Winston
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
$117 nightly
The price is $118
Nov 19 - Nov 20
Total with taxes and fees
the Bunkhouse coyote- Private Studio Retreat Room
Interior
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Roseburg
9.4 out of 10, Exceptional, (19)
"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.
$159 nightly
The price is $174
Nov 22 - Nov 23
Total with taxes and fees
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Deluxe Apartment, City View | Private kitchen
Bell Sister Flats

Bell Sister Flats

2.0 star property
Roseburg
$342 nightly
The price is $375
Dec 8 - Dec 9
Total with taxes and fees
Bell Sister Flats
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 Roseburg by IHG

Holiday Inn Express Roseburg by IHG

10/10 Excellent
"They had a couple people work on the front desk so check in was quick and painless. The room was clean. The water was hot bed was comfortable everything you want from a hotel."
jefferson 1-night trip
Posted 3 days ago
Holiday Inn Express Roseburg by IHG

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

River Vista Vacation Homes: You might like this vacation home rental near Winchester. It is located on a river and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker.

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. Melrose Vineyards and Reustle Prayer Rock 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.