Winchester Vacation Rentals

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Dec 5 - Dec 6
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Dec 6 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Winchester

Smart TV, books
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
10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is ￥27,225
￥32,805 total
includes taxes & fees
Dec 7 - Dec 8
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

South Wilmington
2.0 out of 10, (2)
"Never heard from host. Expedia had to cancel reservation."
United States
Josh
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Outdoor dining
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (178)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Fridge, microwave, oven, stovetop
Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!

Kennett Square
10.0 out of 10, Exceptional, (85)
"One of the nicest properties we have stayed at. Fantastic amenities. Highly recommend!!"
United States
Stephen
The price is ￥29,475
￥49,868 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Homey Retreat in Historic Kennett Square!!
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Fridge, microwave, oven, stovetop
Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.

Downtown Wilmington
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
The price is ￥33,497
￥55,785 total
includes taxes & fees
Dec 7 - Dec 8
Two-story condo in luxury townhouse. Free parking.
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (44)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Private kitchen
Room #3 in Elkton, MD – Easy Access to I-95

Room #3 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
8.0 out of 10, Very Good, (1)
"For our first time trying shared spaces. Over all, the pros; The room was in a nice home in a very quiet and decent housing development. The home was neat decorated in a minimalist style. The bed was very comfortable, pillows and bedding, and hot shower and bath water with soap provided. The kitchen/dining area was just right for cooking and dining and cleaning up had the minimal supplies needed. The sitting areas were very relaxing to watch T.V. and or just lounge. Common bathroom off living...
United States
Nicomedes M R.
The price is ￥13,182
￥20,548 total
includes taxes & fees
Dec 21 - Dec 22
Room #3 in Elkton, MD – Easy Access to I-95
Sun loungers, beach towels
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, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is ￥50,123
￥93,254 total
includes taxes & fees
Dec 10 - Dec 11
5-bedroom vacation home 5 minutes from historic Charlestown
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cabin close to Fair Hill on horse farm

Elkton
9.6 out of 10, Exceptional, (14)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥20,936
￥53,261 total
includes taxes & fees
Dec 6 - Dec 7
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis

Bear
Tiny Home Tranquil Oasis
Interior
4-bedroom 2 Full Bath Cozy Retreat

4-bedroom 2 Full Bath Cozy Retreat

2.0 star property
Wilmington
4-bedroom 2 Full Bath Cozy Retreat
Fridge, microwave, oven, stovetop
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
The price is ￥125,655
￥208,507 total
includes taxes & fees
Dec 6 - Dec 7
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is ￥16,754
￥43,247 total
includes taxes & fees
Dec 7 - Dec 8
Historic Chesapeake City Stay
1 bedroom
Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is ￥11,239
￥23,836 total
includes taxes & fees
Dec 6 - Dec 7
Summer Rustic Camping with AC and King Bed
Fridge, microwave, oven, stovetop
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥20,657
￥33,403 total
includes taxes & fees
Dec 7 - Dec 8
Quarry Landing - Center of Town & River View - 3 Bedroom
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

Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG

10/10 Excellent
"Clean room and very good breakfast"
Francis 3-night trip
Posted 1 day ago
Holiday Inn Express & Suites Wilmington-Newark 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This vacation home rental near Winchester is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation 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.