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Winchester Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester vacation rentals

A living room with a white sofa, a clock, a dining area with a table and chairs, and a kitchen in the background.

1. 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, (15 reviews)
"It is in a lovely neighborhood and the hosts were very welcoming of us and my 2 dogs. We were all very comfortable."
United States
Barb
$171 nightly
The price is $181
Oct 26 - Oct 27
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

2. 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)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
$359 nightly
The price is $381
Oct 26 - Oct 27
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

3. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (2 reviews)
"My girlfriend and I were in town for a wedding and the VRBO was perfect. Great privacy, lovely decor, and comfortable bed. A full use kitchen was great to have. Cheech (the pig!!) was so friendly and the host even dropped off carrots for us to feed him. The host responded to every question in a timely manner and check in and check out were painless."
United States
Zachary Z.
$186 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
Cozy 1-bedroom apartment in Lincoln University
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Nov 2 - Nov 3
Total with taxes and fees
Country Get Away Studio Apartment
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

5. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"This is a great place, to feel comfortable. Exactly as advertised Just around the corner from Schaeffers."
United States
Janice H.
$294 nightly
The price is $312
Oct 26 - Oct 27
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.

6. 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.
$211 nightly
The price is $212
Oct 26 - Oct 27
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
A two-story house with a deck, a barbecue grill, and a covered patio area.

7. 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.
$444 nightly
The price is $491
Nov 2 - Nov 3
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

8. 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.
$383 nightly
The price is $383
Nov 5 - Nov 6
Total with taxes and fees
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A living room with a sofa, a television, and shelves with books and decorative items.

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

Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (25 reviews)
"Great rustic setting for a perfect weekend getaway!"
United States
Emily D.
$220 nightly
The price is $243
Oct 26 - Oct 27
Total with taxes and fees
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Exterior

10. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (3 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
$193 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

11. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
$374 nightly
The price is $390
Oct 26 - Oct 27
Total with taxes and fees
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

12. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
$275 nightly
The price is $292
Nov 5 - Nov 6
Total with taxes and fees
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

13. 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, (17 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
$1,507 nightly
The price is $1,518
Oct 30 - Oct 31
Total with taxes and fees
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A courtyard with wicker furniture, a fire pit, and a pool area.

14. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
$168 nightly
The price is $185
Nov 8 - Nov 9
Total with taxes and fees
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
A wooden deck with lounge chairs and a dock extending into calm water.

15. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
$477 nightly
The price is $506
Oct 28 - Oct 29
Total with taxes and fees
Waterfront house with amazing views. Top of the Chesapeake
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

16. 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, (57 reviews)
"Unique charming place to relax."
United States
Nimia N.
$199 nightly
The price is $210
Oct 28 - Oct 29
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

17. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
$471 nightly
The price is $499
Oct 27 - Oct 28
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

18. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"This is a very nice apt. The owner was very receptive to any questions we had, even allowed an early checkin."
United States
Kathleen B.
$310 nightly
The price is $329
Oct 26 - Oct 27
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
A covered deck area with a grill and outdoor seating.

19. 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
Oct 26 - Oct 27
Total with taxes and fees
Nature's Haven Tiny Home
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

20. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (24 reviews)
"Linda's home is perfect for family traveling! Everything you need for cooking, washing, and just enjoying. The back yard and Patio were awesome for Thunderstorm watching. We'll be back !"
United States
Patricia T.
$420 nightly
The price is $463
Oct 26 - Oct 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

Travel Inn

Travel Inn

10/10 Excellent
"Very reasonably priced. Clean rooms. Continental breakfast did not have a lot of options compared to other similar places."
Karen 1-night trip
Posted 4 hours ago
Travel Inn

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.

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.