Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Winchester vacation rentals

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.
$180 nightly
The price is $180
Apr 14 - Apr 15
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
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.
$111 nightly
The price is $112
Apr 16 - Apr 17
Total with taxes and fees
Lil Cedar Lodge
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, (44 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.
$169 nightly
The price is $169
Apr 13 - Apr 14
Total with taxes and fees
Charming, Private Cottage near I-5 and Golf Course.
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
$205 nightly
The price is $224
Apr 13 - Apr 14
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Smart TV, fireplace, books, music library

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Roseburg
9.8 out of 10, Exceptional, (39 reviews)
"As usual this property did not disappoint. Highly recommend! Beds are amazing. "
United States
Barry W.
$295 nightly
The price is $323
Apr 13 - Apr 14
Total with taxes and fees
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
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.
$320 nightly
The price is $350
Apr 13 - Apr 14
Total with taxes and fees
Home Sweet Home
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.
$155 nightly
The price is $158
Apr 24 - Apr 25
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
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)
"Everything was great! "
United States
Candace L.
$356 nightly
The price is $386
Apr 13 - Apr 14
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
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.
$207 nightly
The price is $227
Apr 13 - Apr 14
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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, (94 reviews)
"Host was absolutely fantastic in assisting us with making sure our stay was perfect and peaceful we throughly enjoyed our stay the facilities were perfect for home cooked breakfast and a small family gathering to celebrate Christmas with our grandkids and kids Awill put as a favorite foe our next trip cant say thank you enough."
United States
Brenda L.
$192 nightly
The price is $210
May 2 - May 3
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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.
$217 nightly
The price is $238
Apr 24 - Apr 25
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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.
$165 nightly
The price is $181
Apr 26 - Apr 27
Total with taxes and fees
Downtown Stay at the Blue 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.
$180 nightly
The price is $197
Apr 15 - Apr 16
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
$368 nightly
The price is $403
Apr 18 - Apr 19
Total with taxes and fees
Bell Sister Flats
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.
$156 nightly
The price is $170
Apr 13 - Apr 14
Total with taxes and fees
Downtown Stay at the Red Tiny Twin!
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
$347 nightly
The price is $352
Apr 13 - Apr 14
Total with taxes and fees
Private bungalow with AC in charming Roseburg
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.
$331 nightly
The price is $362
Apr 13 - Apr 14
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
$353 nightly
The price is $387
Apr 13 - Apr 14
Total with taxes and fees
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

Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

10/10 Excellent
"Everything was clean and well-stocked, and the staff was great for my short stay."
Carin 1-night trip
Posted 9 hours ago
Hampton Inn & Suites 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?

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.