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Winchester Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester vacation rentals

Exterior

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 ￥18,714
￥25,127 total
includes taxes & fees
Sep 20 - Sep 21
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Coffee/tea maker, fridge, microwave, oven

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)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥26,246
￥59,395 total
includes taxes & fees
Sep 21 - Sep 22
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Marina

3. 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.
The price is ￥16,843
￥42,154 total
includes taxes & fees
Sep 23 - Sep 24
Historic Chesapeake City Stay
Exterior

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥10,917
￥17,358 total
includes taxes & fees
Sep 28 - Sep 29
Country Get Away Studio Apartment
Coffee/tea maker, fridge, microwave, oven

5. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (1 review)
The price is ￥19,650
￥29,445 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 1-bedroom apartment in Lincoln University
Outdoor dining

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.
The price is ￥20,429
￥34,698 total
includes taxes & fees
Oct 12 - Oct 13
Amish Countryside Escape at Forest Edge Farm
Exterior

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.
The price is ￥32,576
￥73,968 total
includes taxes & fees
Sep 21 - Sep 22
Thunder Hill Retreat - Spacious/Deck/Hot tub
Dining

8. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Newark
2 Full Beds | Non-Smoking
Interior

9. 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, (29 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveler
The price is ￥24,702
￥36,579 total
includes taxes & fees
Sep 20 - Sep 21
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

10. 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.
The price is ￥22,457
￥45,460 total
includes taxes & fees
Sep 30 - Oct 1
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Interior

11. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
10.0 out of 10, Exceptional, (41 reviews)
"Very cool place! "
United States
Scott M.
The price is ￥15,439
￥45,054 total
includes taxes & fees
Sep 23 - Sep 24
Underground Railroad Barn
Exterior

12. 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.
The price is ￥26,667
￥30,304 total
includes taxes & fees
Sep 27 - Sep 28
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Coffee/tea maker, fridge, microwave, oven

13. Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
10.0 out of 10, Exceptional, (34 reviews)
"Comfortable, clean, thoughtfully stocked property. We would definitely stay again!"
United States
Amy Y.
The price is ￥15,439
￥43,435 total
includes taxes & fees
Sep 22 - Sep 23
Underground Railroad 4 Bedroom Farmhouse
Exterior

14. 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, (53 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is ￥27,369
￥32,813 total
includes taxes & fees
Sep 20 - Sep 21
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio

15. 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 ￥30,990
￥65,455 total
includes taxes & fees
Oct 18 - Oct 19
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Microwave, oven, stovetop, dishwasher

16. Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.6 out of 10, Excellent, (22 reviews)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is ￥19,026
￥72,330 total
includes taxes & fees
Sep 29 - Sep 30
Kennett Square, Near Longwood Gardens & Downtown
Terrace/patio

17. 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 ￥29,475
￥36,416 total
includes taxes & fees
Sep 20 - Sep 21
Nature's Haven Tiny Home
Smart TV, fireplace, foosball, table tennis

18. 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, (15 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is ￥130,550
￥230,648 total
includes taxes & fees
Sep 21 - Sep 22
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Exterior

19. Cottage 3BR Near Longwood Gardens

Cottage 3BR Near Longwood Gardens
Avondale
The price is ￥25,264
￥60,952 total
includes taxes & fees
Sep 20 - Sep 21
Cottage 3BR Near Longwood Gardens
TV, books, stereo

20. Cozy Comfy Pet Friendly House in a Quiet Neighborhood

Cozy Comfy Pet Friendly House in a Quiet Neighborhood
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
The price is ￥23,860
￥30,081 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Comfy Pet Friendly House in a Quiet Neighborhood
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 Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

10/10 Excellent
"Wonderful everything was staff and vibe"
Jeremy 1-night trip
Posted 1 hour ago
Sonesta Select Newark Christiana Mall

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:

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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. Fair Hill Equestrian Center and University of Delaware 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.