Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Winchester vacation rentals

Exterior

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is ￥11,073
￥17,606 total
includes taxes & fees
Jan 27 - Jan 28
Country Get Away 1 Bedroom Apartment
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"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 ￥17,085
￥44,101 total
includes taxes & fees
Jan 22 - Jan 23
Historic Chesapeake City Stay
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
2.0 star property
Nottingham
9.2 out of 10, Wonderful, (15 reviews)
"The farm was a little trick to get to but with the detailed directions from our hosts we were able to find it. Place was lovely and exactly what we needed "
United States
Stephen B.
The price is ￥25,057
￥36,937 total
includes taxes & fees
Jan 22 - Jan 23
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
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 reviews)
"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 ￥12,007
￥24,852 total
includes taxes & fees
Jan 22 - Jan 23
Summer Rustic Camping with AC and King Bed
TV, fireplace

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
2.0 star property
Trolley Square
8.0 out of 10, Very Good, (3 reviews)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is ￥16,860
￥59,937 total
includes taxes & fees
Jan 22 - Jan 23
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
Smart TV, foosball, books

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ￥28,474
￥52,987 total
includes taxes & fees
Jan 22 - Jan 23
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Interior

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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is ￥21,356
￥44,436 total
includes taxes & fees
Jan 22 - Jan 23
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Smart TV

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
2.0 star property
Elkton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥18,983
￥25,488 total
includes taxes & fees
Jan 22 - Jan 23
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (23 reviews)
"This home was perfect! It was beautifully maintained, large rooms and equipped with everything needed during our our stay. Lisa was responsive, attentive and available for all of our questions and requests. We would definitely return to this property if we are in the Wilmington area. "
United States
Lori A.
The price is ￥18,983
￥27,905 total
includes taxes & fees
Jan 22 - Jan 23
New Construction townhome close to everything downtown w/transparent pricing
Interior

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is ￥14,553
￥18,372 total
includes taxes & fees
Jan 22 - Jan 23
Cozy loft above ink shop
Dining

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, (21 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 ￥30,610
￥52,711 total
includes taxes & fees
Jan 29 - Jan 30
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Outdoor dining

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

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
2.0 star property
Newark
The price is ￥28,916
￥36,210 total
includes taxes & fees
Feb 1 - Feb 2
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Smart TV

Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens

Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
Kennett Square
10.0 out of 10, Exceptional, (38 reviews)
"They had everything you may need there just in case and a great location. Beautiful place to stay!"
United States
William R.
The price is ￥29,186
￥56,161 total
includes taxes & fees
Jan 22 - Jan 23
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
Property grounds

Entire place with private parking

Entire place with private parking
Hilltop
7.6 out of 10, Good, (10 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is ￥13,921
￥23,248 total
includes taxes & fees
Jan 22 - Jan 23
Entire place with private parking
Fridge, microwave, oven, stovetop

Homey Retreat in Historic Kennett Square!!

Homey Retreat in Historic Kennett Square!!
Kennett Square
10.0 out of 10, Exceptional, (91 reviews)
"One of the nicest properties we have stayed at. Fantastic amenities. Highly recommend!!"
United States
Stephen
The price is ￥30,056
￥51,187 total
includes taxes & fees
Jan 25 - Jan 26
Homey Retreat in Historic Kennett Square!!
Interior

Underground Railroad Barn

Underground Railroad Barn
Kennett Square
10.0 out of 10, Exceptional, (32 reviews)
"Clean and welcoming. We enjoyed the open design and especially the back patio."
United States
Lauren S.
The price is ￥19,774
￥50,570 total
includes taxes & fees
Jan 25 - Jan 26
Underground Railroad Barn
Fridge, microwave, oven, stovetop

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 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥21,071
￥33,570 total
includes taxes & fees
Jan 27 - Jan 28
Quarry Landing - Center of Town & River View - 3 Bedroom
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, (2 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥21,356
￥53,994 total
includes taxes & fees
Jan 22 - Jan 23
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Microwave, oven, stovetop, dishwasher

Kennett Square, Near Longwood Gardens & Downtown

Kennett Square, Near Longwood Gardens & Downtown
Kennett Square
8.0 out of 10, Very Good, (16 reviews)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is ￥19,299
￥73,871 total
includes taxes & fees
Feb 1 - Feb 2
Kennett Square, Near Longwood Gardens & Downtown
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, (17 reviews)
"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 ￥34,169
￥56,904 total
includes taxes & fees
Jan 25 - Jan 26
Two-story condo in luxury townhouse. Free parking.
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
"Staff was amazing, breakfast was good, lots of choices, room was clean, easy parking"
Karen 2-night trip
Posted 2 days ago
Sonesta ES Suites Wilmington - Newark

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?

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington: This vacation home rental near Winchester offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.