Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
The price is ￥21,891
￥27,211 total
includes taxes & fees
Nov 8 - Nov 9
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)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is ￥28,632
￥59,898 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is ￥19,844
￥27,399 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom apartment in Lincoln University
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, (25 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is ￥36,678
￥75,556 total
includes taxes & fees
Nov 9 - Nov 10
Thunder Hill Retreat - Spacious/Deck/Hot tub
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

5. 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 ￥17,894
￥30,537 total
includes taxes & fees
Nov 16 - Nov 17
Amish Countryside Escape at Forest Edge Farm
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

6. 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.
The price is ￥11,024
￥16,193 total
includes taxes & fees
Nov 16 - Nov 17
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.

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is ￥21,261
￥45,073 total
includes taxes & fees
Nov 8 - Nov 9
Historic Chesapeake City Stay
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, (8 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is ￥26,987
￥58,170 total
includes taxes & fees
Dec 2 - Dec 3
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

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

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 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
The price is ￥22,679
￥42,236 total
includes taxes & fees
Nov 8 - Nov 9
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

10. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is ￥49,096
￥73,248 total
includes taxes & fees
Nov 9 - Nov 10
Long Beach Cottage, (romantic couple’s getaway)
A wooden deck with lounge chairs and a dock extending into calm water.

11. 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)
"Host was very communicative."
United States
Lee Anne K.
The price is ￥41,105
￥79,296 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront house with amazing views. Top of the Chesapeake
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.

12. 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, (6 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 ￥38,313
￥62,444 total
includes taxes & fees
Nov 10 - Nov 11
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

13. 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)
"What a great stay and a beautiful farm. We really enjoyed visiting the animals and hiking to the vinery."
United States
Anastasia T.
The price is ￥26,224
￥36,900 total
includes taxes & fees
Nov 8 - Nov 9
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

14. 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.
The price is ￥33,876
￥74,472 total
includes taxes & fees
Nov 16 - Nov 17
5-bedroom vacation home 5 minutes from historic Charlestown
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

15. 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
9.8 out of 10, Exceptional, (7 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 ￥39,373
￥44,610 total
includes taxes & fees
Nov 10 - Nov 11
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A courtyard with wicker furniture, a fire pit, and a pool area.

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

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
10.0 out of 10, Exceptional, (1 review)
"Clean rooms close to all things we needed breakfast was good and plentiful wish the afternoon buffet was available would use this place again"
United States
Susan H.
The price is ￥41,306
￥48,212 total
includes taxes & fees
Nov 8 - Nov 9
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
A covered deck area with a grill and outdoor seating.

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 ￥29,766
￥35,358 total
includes taxes & fees
Nov 10 - Nov 11
Nature's Haven Tiny Home
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a tiled backsplash.

18. Cottage 3BR Near Longwood Gardens

Cottage 3BR Near Longwood Gardens
Avondale
Cottage 3BR Near Longwood Gardens
Exterior

19. 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 ￥29,057
￥30,559 total
includes taxes & fees
Nov 8 - Nov 9
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
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

A Holiday Inn Express & Suites hotel with a stone facade, multiple windows, and a prominent entrance with a covered walkway.
Holiday Inn Express & Suites Elkton - University Area by IHG

Holiday Inn Express & Suites Elkton - University Area by IHG

Holiday Inn Express & Suites Elkton - University Area by IHG
Elkton

10/10 Excellent

The young women who checked us in & the women who checked us out were efficient and delightful. The rooms were excellent in every way especially the beds, pillows & sheets! Such an immaculately clean hotel everywhere.
United States
Paula
Reviewed July 22, 2022
Holiday Inn Express & Suites Elkton - University Area by IHG

Find out more about Winchester

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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. 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.