Winchester Vacation Rentals

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Dec 1 - Dec 2
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Dec 2 - Dec 3
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Winchester

Terrace/patio
the Bunkhouse coyote- Private Studio Retreat Room

Apartment in Winston

2.0 star property
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
Dec 2 - Dec 3
Total with taxes and fees
the Bunkhouse coyote- Private Studio Retreat Room
Terrace/patio
A Restful Studio Near a Creek and Forest - Pets

Vacation Home in Roseburg

10.0 out of 10, Exceptional, (40)
"Great place! The only thing I’d change is some blackout curtains if folks wanted to sleep in! Otherwise everything was amazing, Very sweet host and not to mention the beautiful property! "
United Kingdom
Hunter S.
$181 nightly
The price is $181
Dec 4 - Dec 5
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Vacation Home in Roseburg

10.0 out of 10, Exceptional, (23)
"My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received"
United States
SharonLee S.
$222 nightly
The price is $243
Dec 2 - Dec 3
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Fridge, microwave, oven, stovetop
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Apartment in Roseburg

2.0 star property
10.0 out of 10, Exceptional, (3)
"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.
$304 nightly
The price is $333
Dec 4 - Dec 5
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
1 bedroom, bed sheets
Lil Cedar Lodge

Cabin in Roseburg

$111 nightly
The price is $112
Dec 2 - Dec 3
Total with taxes and fees
Lil Cedar Lodge
Interior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Vacation Home in Roseburg

9.8 out of 10, Exceptional, (90)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
$203 nightly
The price is $222
Dec 2 - Dec 3
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Vacation Home in Roseburg North

9.4 out of 10, Exceptional, (18)
"great property"
United States
Mai
$441 nightly
The price is $448
Dec 3 - Dec 4
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Exterior
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Vacation Home in Roseburg

9.6 out of 10, Exceptional, (36)
"Nice place, great location."
United States
Gordon
$209 nightly
The price is $229
Dec 28 - Dec 29
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Vacation Home in Roseburg

9.6 out of 10, Exceptional, (19)
"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.
$166 nightly
The price is $182
Dec 5 - Dec 6
Total with taxes and fees
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway

Vacation Home in Winston

10.0 out of 10, Exceptional, (47)
"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
Dec 2 - Dec 3
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

Vacation Home in Roseburg

9.6 out of 10, Exceptional, (13)
"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
Dec 2 - Dec 3
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
Dining
Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Vacation Home in Glide

2.0 star property
$506 nightly
The price is $513
Dec 26 - Dec 27
Total with taxes and fees
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Fridge, microwave, oven, stovetop
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Vacation Home in Roseburg

9.8 out of 10, Exceptional, (37)
"Just as advertised! Great house. Would definitely stay there again."
United States
Jake G.
$270 nightly
The price is $296
Dec 14 - Dec 15
Total with taxes and fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Private kitchen
Home Sweet Home

Vacation Home in Sutherlin

8.6 out of 10, Excellent, (10)
"We really enjoyed our stay! There are super comfortable beds, comfortable couch, fantastic washing machine, nice front porch and clean kitchen! The host was communicative and friendly ! Would for sure recommend and will stay there again on our next trip! "
United States
A T.
$140 nightly
The price is $153
Dec 2 - Dec 3
Total with taxes and fees
Home Sweet Home
Interior
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Vacation Home in 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.
$165 nightly
The price is $181
Dec 3 - Dec 4
Total with taxes and fees
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior
Charming, Private Cottage near I-5 and Golf Course.

Cottage in Myrtle Creek

10.0 out of 10, Exceptional, (41)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
$180 nightly
The price is $180
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming, Private Cottage near I-5 and Golf Course.
Outdoor spa tub
Private bungalow with AC in charming Roseburg

Vacation Home in Roseburg

2.0 star property
$338 nightly
The price is $343
Dec 2 - Dec 3
Total with taxes and fees
Private bungalow with AC in charming Roseburg
Deluxe Apartment, City View | Private kitchen
Bell Sister Flats

Aparthotel in Roseburg

2.0 star property
$347 nightly
The price is $381
Dec 4 - Dec 5
Total with taxes and fees
Bell Sister Flats
Terrace/patio
Bunkhouse Bear Room -Private Studio Retreat

Apartment in Roseburg

2.0 star property
$136 nightly
The price is $138
Jan 1 - Jan 2, 2026
Total with taxes and fees
Bunkhouse Bear Room -Private Studio Retreat
Fridge, microwave, oven, stovetop
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Vacation Home in Roseburg

9.6 out of 10, Exceptional, (51)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
$212 nightly
The price is $232
Dec 4 - Dec 5
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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

Riverfront Inn Roseburg

Riverfront Inn Roseburg

10/10 Excellent
"I was pleased they had left the lights on for our after dark arrival. The pet area was convenient to the room and really nice. I will stay again. "
Julie 1-night trip
Posted 1 day ago
Riverfront Inn Roseburg

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: Located near Winchester, this vacation home rental 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.