Winchester Vacation Rentals

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Oct 17 - Oct 19
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Jan 23 - Jan 25

Vacation Rentals in Winchester

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
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

9.8 out of 10, Exceptional, (33)
"Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! "
$267 nightly
The price is $292
Oct 6 - Oct 7
Total with taxes and fees
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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
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, (48)
"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."
$210 nightly
The price is $230
Oct 2 - Oct 3
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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, (33)
"Nice place, great location."
$196 nightly
The price is $215
Oct 2 - Oct 3
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (46)
"This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team. "
$360 nightly
The price is $390
Oct 6 - Oct 7
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
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."
$159 nightly
The price is $174
Oct 5 - Oct 6
Total with taxes and fees
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
<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, (88)
"It was wonderful to go back in time, furniture, turn table all brought back delightful memories of my childhood. Thanks for sharing your place with us. "
$198 nightly
The price is $217
Oct 19 - Oct 20
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

$106 nightly
The price is $108
Oct 15 - Oct 16
Total with taxes and fees
Lil Cedar Lodge
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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

9.4 out of 10, Exceptional, (23)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
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, (57)
"Amazing!"
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)
"Peaceful and clean."
$165 nightly
The price is $165
Oct 4 - Oct 5
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (12)
"great property"
$441 nightly
The price is $448
Oct 2 - Oct 3
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
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)
"The property was as described. Quiet and beautiful location. My partner and I had a magical time on our mini vacation!"
$155 nightly
The price is $158
Oct 3 - Oct 4
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
Indigo Collective - Modern Comfort & Bold Design
Microwave, oven, stovetop, dishwasher

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (22)
"We had a lovely 3 generation family visit. "
Indigo Collective - Modern Comfort & Bold Design
Family home
Fridge, microwave, oven, stovetop

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (17)
"Enjoyed the accommodations. just as advertised would stay again."
$159 nightly
The price is $174
Oct 4 - Oct 5
Total with taxes and fees
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Bell Sister Flats
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

2.0 star property
$444 nightly
The price is $487
Nov 1 - Nov 2
Total with taxes and fees
Bell Sister Flats
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
Home Sweet Home
Private kitchen

Home Sweet Home

9.6 out of 10, Exceptional, (5)
Home Sweet Home
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

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

10/10 Excellent
"The cleanliness of this facility is outstanding ,the room is soft and clean "
Gerri Yvette 14-night trip
Posted 22 hours ago
Motel 6 Roseburg, OR

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 $108 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.