Search Vacation Homes in Winchester

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winchester vacation homes

1 bedroom
Summer Rustic Camping with AC and King Bed

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.
$158 nightly
The price is $159
Dec 11 - Dec 12
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
Interior
Underground Railroad Barn

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (28)
"Great property. Good for dogs, full fenced in yard. "
United States
David R.
$270 nightly
The price is $307
Jan 4 - Jan 5, 2026
Total with taxes and fees
Underground Railroad Barn
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

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.
$322 nightly
The price is $341
Dec 11 - Dec 12
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
2 bedrooms, WiFi
Private townhouse near downtown and state park

Private townhouse near downtown and state park

Private townhouse near downtown and state park
Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Great little spot in a perfect location for us"
United States
j m.
$276 nightly
The price is $283
Dec 11 - Dec 12
Total with taxes and fees
Private townhouse near downtown and state park
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.0 out of 10, Very Good, (10)
"Nice and quiet place to stay"
United States
Gary M.
$268 nightly
The price is $284
Dec 15 - Dec 16
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Interior
Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.0 out of 10, Very Good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
$434 nightly
The price is $479
Dec 18 - Dec 19
Total with taxes and fees
Kennett Square, Near Longwood Gardens & Downtown
Property grounds
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (22)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
$176 nightly
The price is $182
Dec 17 - Dec 18
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Interior
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

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

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
2.0 star property
Nottingham
9.2 out of 10, Wonderful, (13)
"We had an excellent stay"
United States
Meagan
$211 nightly
The price is $234
Dec 11 - Dec 12
Total with taxes and fees
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Interior
Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
9.8 out of 10, Exceptional, (23)
"Very nice and clean! "
United States
Virginie M.
$346 nightly
The price is $392
Jan 4 - Jan 5, 2026
Total with taxes and fees
Underground Railroad 4 Bedroom Farmhouse
Interior
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

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.4 out of 10, Exceptional, (20)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
$357 nightly
The price is $367
Dec 30 - Dec 31
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Private kitchen
Room #2 in Elkton, MD – Easy Access to I-95

Room #2 in Elkton, MD – Easy Access to I-95

Room #2 in Elkton, MD – Easy Access to I-95
2.0 star property
Elkton
$101 nightly
The price is $107
Dec 18 - Dec 19
Total with taxes and fees
Room #2 in Elkton, MD – Easy Access to I-95
Dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
2.0 star property
Nottingham
$197 nightly
The price is $198
Dec 11 - Dec 12
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Interior
3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
Elkton
10.0 out of 10, Exceptional, (1)
"Yes. Very welcoming. Great location. Overall good "
United States
Anonymous traveler
$360 nightly
The price is $382
Dec 11 - Dec 12
Total with taxes and fees
3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
Private kitchen
A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE
Wilmington
$150 nightly
The price is $155
Dec 11 - Dec 12
Total with taxes and fees
A Cool Place to Stay in Wilmington DE
A heated pool
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
2.0 star property
Middletown
$457 nightly
The price is $487
Dec 16 - Dec 17
Total with taxes and fees
Heated Pool • Private Backyard • Home Theater
Fridge, microwave, oven, stovetop
Homey Retreat in Historic Kennett Square!!

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
$290 nightly
The price is $320
Jan 4 - Jan 5, 2026
Total with taxes and fees
Homey Retreat in Historic Kennett Square!!
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

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.
$567 nightly
The price is $601
Dec 11 - Dec 12
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Fridge, microwave, oven, stovetop
The Historic Walton House by RPG

The Historic Walton House by RPG

The Historic Walton House by RPG
Kennett Square
10.0 out of 10, Exceptional, (38)
"I couldn’t rate our stay any higher! The property, the location, the communication were all subperb. I would stay here again and again. "
United States
Tina S.
$654 nightly
The price is $722
Dec 15 - Dec 16
Total with taxes and fees
The Historic Walton House by RPG
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.

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.
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Interior
Unique 10 bedrooms for 20+Person

Unique 10 bedrooms for 20+Person

Unique 10 bedrooms for 20+Person
2.0 star property
Baynard Village
$1,867 nightly
The price is $1,931
Dec 11 - Dec 12
Total with taxes and fees
Unique 10 bedrooms for 20+Person
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

Hampton Inn & Suites Wilmington Christiana

Hampton Inn & Suites Wilmington Christiana

10/10 Excellent
"Clean and comfortable. Great value and excellent breakfast included "
Sebastian 1-night trip
Posted 1 day ago
Hampton Inn & Suites Wilmington Christiana

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
392
Accommodation
173 Vacation Homes
Lowest Price
$107
Highest Price
$1,931

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