Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winchester vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
$263 nightly
The price is $279
May 24 - May 25
Total with taxes and fees
Historic Chesapeake City Stay
Smart TV

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
May 27 - May 28
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Fridge, microwave, oven, dishwasher

Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
9.8 out of 10, Exceptional, (28 reviews)
"Great location and charming farm house!"
United States
Oliver G.
$245 nightly
The price is $279
May 25 - May 26
Total with taxes and fees
Underground Railroad 4 Bedroom Farmhouse
Interior

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (35 reviews)
"Loved the location and place was comfortable. Our dogs loved the fenced back yard."
United States
James C.
$244 nightly
The price is $277
May 26 - May 27
Total with taxes and fees
Underground Railroad Barn
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
$105 nightly
The price is $111
Jun 8 - Jun 9
Total with taxes and fees
Country Get Away Studio Apartment
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
$230 nightly
The price is $239
May 24 - May 25
Total with taxes and fees
Tiny Home Tranquil Oasis
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
$223 nightly
The price is $232
May 24 - May 25
Total with taxes and fees
Nature's Haven Tiny Home
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
$197 nightly
The price is $208
Jun 1 - Jun 2
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$250 nightly
The price is $265
May 27 - May 28
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
$172 nightly
The price is $173
Jun 10 - Jun 11
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
Fridge, microwave, oven, stovetop

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$321 nightly
The price is $340
May 24 - May 25
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Dining

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (21 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
$320 nightly
The price is $328
May 24 - May 25
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.4 out of 10, Exceptional, (19 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveler
$210 nightly
The price is $232
May 25 - May 26
Total with taxes and fees
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
$199 nightly
The price is $200
Jun 9 - Jun 10
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (9 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
$192 nightly
The price is $203
May 27 - May 28
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$503 nightly
The price is $527
May 27 - May 28
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Fridge, microwave, oven, stovetop

Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (18 reviews)
"Comfortable place, wonderful amenities, and a gracious host. "
United States
Donald H.
$347 nightly
The price is $357
May 25 - May 26
Total with taxes and fees
Two-story condo in luxury townhouse. Free parking.
Outdoor dining

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
$265 nightly
The price is $291
May 31 - Jun 1
Total with taxes and fees
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (27 reviews)
"This condo was in a great location and was very clean and nice. Easy access to the beach and local restaurants and shops. "
United States
Peter F.
$212 nightly
The price is $217
May 25 - May 26
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Microwave, oven, stovetop, dishwasher

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.4 out of 10, Very Good, (19 reviews)
"Our host was very friendly and easy to communicate with! The house was super clean and had everything that we needed. The neighborhood is very nice. We visited Longwood Garden during our stay. It was spectacular! I highly recommend this property!"
United States
Sharon F.
$421 nightly
The price is $465
May 26 - May 27
Total with taxes and fees
Kennett Square, Near Longwood Gardens & Downtown
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

Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

2/10 Terrible
"Roaches"
Aaron 3-night trip
Posted less than an hour ago
Red Roof Inn PLUS+ Wilmington - Newark

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 $111 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

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near top local attractions in Winchester, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Winchester has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Winchester is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Plumpton Park Zoo, or get outside and enjoy nature at Fair Hill State Natural Resources Management Area. University of Delaware and University of Delaware Botanic Gardens are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can stay in for several days or longer in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.