Winchester Vacation Rentals

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Sep 26 - Sep 28
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Oct 10 - Oct 12
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Dec 5 - Dec 7

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

Singing Waters at N. Umpqua
Interior

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (8)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
Singing Waters at N. Umpqua
River Vista Vacation Homes
Property entrance

River Vista Vacation Homes

3.0 star property
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!"
River Vista Vacation Homes
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (31)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
$198 nightly
The price is $217
Sep 19 - Sep 20
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (47)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
$189 nightly
The price is $207
Sep 12 - Sep 13
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (62)
"Wonderful property,had everything we needed,Thankyou again"
Firewater Lodge Cabin Experience
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

$111 nightly
The price is $112
Sep 14 - Sep 15
Total with taxes and fees
Lil Cedar Lodge
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
$168 nightly
The price is $171
Oct 2 - Oct 3
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Interior

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

9.8 out of 10, Exceptional, (84)
"April answered all my emails immediately and was very nice. Loved the location."
$198 nightly
The price is $217
Sep 13 - Sep 14
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (45)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
$362 nightly
The price is $392
Sep 21 - Sep 22
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (15)
"Enjoyed the accommodations. just as advertised would stay again."
$159 nightly
The price is $174
Sep 21 - Sep 22
Total with taxes and fees
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.2 out of 10, Wonderful, (10)
"great property"
$527 nightly
The price is $534
Sep 14 - Sep 15
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Bell Sister Flats
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

2.0 star property
$393 nightly
The price is $431
Sep 19 - Sep 20
Total with taxes and fees
Bell Sister Flats
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

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."
$154 nightly
The price is $169
Sep 14 - Sep 15
Total with taxes and fees
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (32)
"Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! "
$272 nightly
The price is $297
Sep 22 - Sep 23
Total with taxes and fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Home Sweet Home
Private kitchen

Home Sweet Home

9.6 out of 10, Exceptional, (5)
Home Sweet Home
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Property grounds

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

9.8 out of 10, Exceptional, (56)
"House has the most amazing views. Perfect location for hiking all of the waterfalls. We would most definitely stay again!"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (37)
"Very nice property. "
$166 nightly
The price is $166
Oct 3 - Oct 4
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
Southern Oregon Cabin: Fire Pit & Private Pond!
House (1 Bedroom) | Interior

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
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."
Southern Oregon Cabin: Fire Pit & Private Pond!
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (59)
"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. "
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Charming 3-bedroom cabin on Little River near 8 picturesque water falls
Property grounds

Charming 3-bedroom cabin on Little River near 8 picturesque water falls

2.0 star property
2.0 out of 10, (1)
"This property is atrocious, people lived in the house until the day before our stay which was booked in early March. The greeting coming in is a sign that says slow the fuck down then a pot plant and trash ,this house is not equipped with anything there was other peoples things in the house and people on the property entering the house while we weren't there, feeding cats on the back patio ,most of the time we were without water,the faucet in the tub was a i in pcv pipe with a nob to turn it off...
Charming 3-bedroom cabin on Little River near 8 picturesque water falls
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 always try to stay at the riverfront. Even packed out they have a quiet clientele in a beautiful park like setting. "
carolyn 2-night trip
Posted 1 day ago
Riverfront Inn Roseburg

Find out more about Winchester

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

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: This vacation home rental near Winchester 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 kitchenware.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Douglas County Museum of History and Natural History, 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.