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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

A single-story house with a front porch, a small garden, and a clear blue sky.

1. Cottage 3BR Near Longwood Gardens

Cottage 3BR Near Longwood Gardens
Avondale
$347 nightly
The price is $383
Sep 29 - Sep 30
Total with taxes and fees
Cottage 3BR Near Longwood Gardens
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

2. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Elkton
10.0 out of 10, Exceptional, (14 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
$1,470 nightly
The price is $1,481
Sep 9 - Sep 10
Total with taxes and fees
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

3. 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
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Sep 9 - Sep 10
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A two-story house with a deck, a barbecue grill, and a covered patio area.

4. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
$443 nightly
The price is $490
Sep 14 - Sep 15
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

5. 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
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$359 nightly
The price is $381
Sep 21 - Sep 22
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A wooden cabin with a porch, surrounded by dense forest.

6. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (48 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Sep 15 - Sep 16
Total with taxes and fees
Country Get Away Studio Apartment
A riverside dock with boats, a covered seating area, and a bridge in the background.

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
$257 nightly
The price is $272
Sep 9 - Sep 10
Total with taxes and fees
Historic Chesapeake City Stay
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

8. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 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.
$204 nightly
The price is $205
Sep 9 - Sep 10
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

9. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (1 review)
$171 nightly
The price is $189
Sep 9 - Sep 10
Total with taxes and fees
Cozy 1-bedroom apartment in Lincoln University
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

10. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
$359 nightly
The price is $359
Sep 21 - Sep 22
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A covered deck area with a grill and outdoor seating.

11. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
$225 nightly
The price is $234
Sep 9 - Sep 10
Total with taxes and fees
Nature's Haven Tiny Home
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

12. 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
9.6 out of 10, Exceptional, (27 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveler
$212 nightly
The price is $235
Sep 9 - Sep 10
Total with taxes and fees
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
A room with a bed, a dresser, a window with curtains, and an air conditioning unit.

13. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
$322 nightly
The price is $342
Sep 9 - Sep 10
Total with taxes and fees
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

14. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
$233 nightly
The price is $242
Sep 9 - Sep 10
Total with taxes and fees
Tiny Home Tranquil Oasis
A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

15. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$400 nightly
The price is $424
Sep 23 - Sep 24
Total with taxes and fees
Bohemia Manor Farm
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

16. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
$285 nightly
The price is $296
Sep 11 - Sep 12
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A beach with a water tower, beach umbrellas, and a hotel in the background.

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

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
$233 nightly
The price is $256
Sep 10 - Sep 11
Total with taxes and fees
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

18. 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
9.8 out of 10, Exceptional, (52 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
$200 nightly
The price is $211
Sep 9 - Sep 10
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

19. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (161 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
$509 nightly
The price is $540
Sep 16 - Sep 17
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

20. 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.
$586 nightly
The price is $616
Sep 22 - Sep 23
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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 Wilmington Christiana

Hampton Inn & Suites Wilmington Christiana

10/10 Excellent
"Everything was as expected"
Kimberly 3-night trip
Posted 4 hours ago
Hampton Inn & Suites Wilmington Christiana

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 $196 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.

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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, 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.