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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winchester holiday rentals

A residential house with a brick exterior, a dark roof, and a front porch with a bench.

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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$940
HK$1,263 total
includes taxes & fees
6 Sept - 7 Sept
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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.
The price is HK$6,562
HK$11,601 total
includes taxes & fees
8 Sept - 9 Sept
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

3. 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.
The price is HK$1,192
HK$2,867 total
includes taxes & fees
8 Sept - 9 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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.
The price is HK$1,529
HK$3,605 total
includes taxes & fees
2 Sept - 3 Sept
Thunder Hill Retreat - Spacious/Deck/Hot tub
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

5. 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.
The price is HK$1,959
HK$2,298 total
includes taxes & fees
24 Sept - 25 Sept
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A riverside dock with boats, a covered seating area, and a bridge in the background.

6. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 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.
The price is HK$846
HK$2,218 total
includes taxes & fees
8 Sept - 9 Sept
Historic Chesapeake City Stay
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

7. 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, (51 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is HK$1,375
HK$1,666 total
includes taxes & fees
6 Sept - 7 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A covered deck area with a grill and outdoor seating.

8. 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
The price is HK$1,481
HK$1,853 total
includes taxes & fees
1 Sept - 2 Sept
Nature's Haven Tiny Home
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

9. 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.
The price is HK$988
HK$1,697 total
includes taxes & fees
21 Sept - 22 Sept
Amish Countryside Escape at Forest Edge Farm
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

10. 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)
"Beautiful, rustic apartment on a farm was the perfect relaxing environment we needed for the weekend. Loved walking around the wooded grounds and meeting the farm animals. The apartment itself was spacious, clean, and comfortable. Will definitely try to cone back. "
United States
Jeff J.
The price is HK$1,241
HK$1,863 total
includes taxes & fees
3 Sept - 4 Sept
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

11. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
The price is HK$1,097
HK$1,635 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-bedroom apartment in Lincoln University
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

12. 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.
The price is HK$1,126
HK$2,810 total
includes taxes & fees
31 Aug - 1 Sept
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

13. 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.
The price is HK$1,481
HK$1,893 total
includes taxes & fees
5 Sept - 6 Sept
Tiny Home Tranquil Oasis
A covered outdoor seating area with wicker chairs and a table, overlooking a body of water.

14. 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, (3 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.
The price is HK$2,758
HK$4,335 total
includes taxes & fees
20 Sept - 21 Sept
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A dining area with a rectangular table, red chairs, and hanging pendant lights.

15. 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, (25 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is HK$1,516
HK$2,611 total
includes taxes & fees
7 Sept - 8 Sept
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
A wooden cabin with a porch, surrounded by dense forest.

16. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is HK$549
HK$872 total
includes taxes & fees
1 Sept - 2 Sept
Country Get Away Studio Apartment
A brick house with a front porch, a chimney, and a well-maintained lawn.

17. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,850
HK$3,021 total
includes taxes & fees
8 Sept - 9 Sept
Bohemia Manor Farm

18. 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, (2 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.
The price is HK$1,293
HK$1,492 total
includes taxes & fees
28 Aug - 29 Aug
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A two-story residential building with a stone facade, a large front lawn, and a driveway.

19. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is HK$2,109
HK$2,957 total
includes taxes & fees
29 Aug - 30 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

20. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"The Port Deposit area is a favorite "mini-vacation" location with great bars/restaurants and beautiful walks. We've stayed at this property a number of times and we've found the rooms to be perfect for our needs. "
United States
Lance W.
The price is HK$1,293
HK$2,284 total
includes taxes & fees
27 Aug - 28 Aug
Private 3 room Queen Suite w/Kitchenette
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

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

10/10 Excellent
"The hotel needs to remove the carpet."
Hassan 1-night trip
Posted 6 hours ago
Sonesta ES Suites Wilmington - Newark

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Winchester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 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. Fair Hill Equestrian Center and University of Delaware are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.