Find hotels in Winchester, MD from ￥9,253

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Dec 3 - Dec 4
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Dec 4 - Dec 5
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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Compare 640 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Park view
Staybridge Suites Wilmington Downtown by IHG

Staybridge Suites Wilmington Downtown by IHG

3.0 star property
Downtown Wilmington
9.4 out of 10, Exceptional, (921)
"Great room great service "
United States
Julie
The price is ￥18,543
￥20,398 total
includes taxes & fees
Dec 29 - Dec 30
Staybridge Suites Wilmington Downtown by IHG
Exterior
Hyatt Place Wilmington Riverfront

Hyatt Place Wilmington Riverfront

3.0 star property
Riverfront
9.2 out of 10, Wonderful, (1001)
"Staff are very friendly and helpful. Clean comfortable room, great location."
United States
janet
The price is ￥22,347
￥24,582 total
includes taxes & fees
Dec 25 - Dec 26
Hyatt Place Wilmington Riverfront
Lobby
Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

3.5 star property
Downtown Wilmington
8.4 out of 10, Very Good, (1011)
"Rooms are very nice."
United States
Stephen
The price is ￥18,543
￥20,396 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sheraton Suites Wilmington Downtown
Terrace/patio
Homewood Suites by Hilton Wilmington Downtown

Homewood Suites by Hilton Wilmington Downtown

3.0 star property
Riverfront
8.8 out of 10, Excellent, (772)
"We really enjoyed the hotel. "
United States
JIEUN
The price is ￥19,814
￥21,795 total
includes taxes & fees
Dec 14 - Dec 15
Homewood Suites by Hilton Wilmington Downtown
Property grounds
Red Roof Inn Perryville

Red Roof Inn Perryville

2.0 star property
Perryville
9.0 out of 10, Wonderful, (111)
"This is an ok place to stay for the price"
Canada
Carla
The price is ￥11,097
￥12,429 total
includes taxes & fees
Dec 14 - Dec 15
Red Roof Inn Perryville
Lobby
Comfort Inn & Suites North East

Comfort Inn & Suites North East

2.5 star property
North East
7.8 out of 10, Good, (645)
"The room was very clean and the staff was fantastic!"
United States
Kenneth
The price is ￥14,490
￥16,228 total
includes taxes & fees
Dec 11 - Dec 12
Comfort Inn & Suites North East
Room, Non Smoking (1 SOFABED PARLOR) | Premium bedding, in-room safe, desk, laptop workspace
DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

4.0 star property
Downtown Wilmington
7.2 out of 10, Good, (1000)
"Great staff and great location. Easy to walk to everything and accessible parking"
United States
Kathy
The price is ￥14,669
￥16,136 total
includes taxes & fees
Dec 20 - Dec 21
DoubleTree by Hilton Downtown Wilmington - Legal District
Exterior
Hilton Garden Inn Kennett Square

Hilton Garden Inn Kennett Square

3.0 star property
Kennett Square
8.4 out of 10, Very Good, (929)
"Great place to stay!"
United States
Kimberly j
The price is ￥19,814
￥21,993 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Kennett Square
Deluxe Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Wingate by Wyndham North East

Wingate by Wyndham North East

2.5 star property
North East
8.0 out of 10, Very Good, (949)
"Room was clean and staff were friendly. They provided a nice breakfast with plenty of options. "
United States
Kathy
The price is ￥18,085
￥20,255 total
includes taxes & fees
Dec 14 - Dec 15
Wingate by Wyndham North East
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
The Westin Wilmington

The Westin Wilmington

4.0 star property
Riverfront
8.8 out of 10, Excellent, (842)
"The room was great, everything was clean and well taken care of. The hotel staff was amazing, and even though it was Thanksgiving eve, the hotel bar was open and served great food!"
United States
Richard
The price is ￥23,668
￥26,035 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Westin Wilmington
Pillowtop beds, desk, iron/ironing board, free cribs/infant beds
Fairfield Inn by Marriott Kennett Square Brandywine Valley

Fairfield Inn by Marriott Kennett Square Brandywine Valley

2.5 star property
Kennett Square
8.8 out of 10, Excellent, (1001)
"Very efficient and friendly front desk"
United States
Randy
The price is ￥21,029
￥23,341 total
includes taxes & fees
Dec 7 - Dec 8
Fairfield Inn by Marriott Kennett Square Brandywine Valley
Outdoor pool, pool umbrellas, sun loungers
Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

3.0 star property
Newark
7.6 out of 10, Good, (1000)
"Friendly staff and Nice room good breakfast!"
United States
James
The price is ￥13,534
￥15,023 total
includes taxes & fees
Dec 18 - Dec 19
Sonesta ES Suites Wilmington - Newark
Outdoor pool
Holiday Inn Express North East by IHG

Holiday Inn Express North East by IHG

2.5 star property
North East
8.4 out of 10, Very Good, (536)
"I like the great hospitality and it was very clean good breakfast also"
United States
Kenneth
The price is ￥14,829
￥16,607 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express North East by IHG
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds
Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
Havre De Grace
6.6 out of 10, (967)
"The rooms reeked of smoke and stale beer. Staff and guests stood around the entryway smoking away. The parking area was covered in bottles and wrappers. The air conditioning in my room literally fell out of the wall when we tried to adjust the temperature "
United States
Judy
The price is ￥8,263
￥9,253 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Super 8 by Wyndham Havre De Grace Aberdeen Area
Reception
Residence Inn by Marriott Wilmington Downtown

Residence Inn by Marriott Wilmington Downtown

3.0 star property
Downtown Wilmington
8.0 out of 10, Very Good, (320)
"Convenient business location with great access to local offices and restaurants. Rooms are clean and spacious. Lobby has comfortable areas to gather. Breakfast was hot and had a good mix of the usual options in this price range. "
United States
Perry
The price is ￥18,381
￥20,219 total
includes taxes & fees
Dec 21 - Dec 22
Residence Inn by Marriott Wilmington Downtown
Lobby
Hotel Du Pont

Hotel Du Pont

4.5 star property
Downtown Wilmington
8.8 out of 10, Excellent, (643)
"Wonderful hotel. "
United States
Nicole
The price is ￥43,339
￥47,672 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hotel Du Pont
Standard Room, 2 Double Beds, Smoking | Desk, free WiFi
Travel Inn

Travel Inn

2.5 star property
New Castle
7.0 out of 10, Good, (247)
"simple room...clean and easy access to airport.."
United States
Ruthann
The price is ￥10,516
￥11,672 total
includes taxes & fees
Dec 4 - Dec 5
Travel Inn
Exterior
Four Points by Sheraton Newark Christiana Wilmington

Four Points by Sheraton Newark Christiana Wilmington

3.0 star property
Newark
8.2 out of 10, Very Good, (975)
"Nice place"
United States
Nelida
The price is ￥13,090
￥14,531 total
includes taxes & fees
Dec 21 - Dec 22
Four Points by Sheraton Newark Christiana Wilmington
Lobby
Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

2.5 star property
Bear
8.2 out of 10, Very Good, (69)
"Clean room and convenient to highway."
United States
Richard
The price is ￥11,821
￥13,122 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Best Western Plus Newark/Christiana Inn
Exterior
The Inn at Montchanin Village, a Historic Hotel of America

The Inn at Montchanin Village, a Historic Hotel of America

3.5 star property
Wilmington
9.2 out of 10, Wonderful, (379)
"I will definitely stay again!"
United States
Joshua
The Inn at Montchanin Village, a Historic Hotel of America
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

Staybridge Suites Wilmington Downtown by IHG

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent
"Yes "
Cynthia 3-night trip
Posted 3 days ago
Staybridge Suites Wilmington Downtown by IHG

More cheap stays in Winchester

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE
The price is ￥9,849 per night from Dec 26 to Dec 27
￥9,849
￥10,932 total
Dec 26 - Dec 27
includes taxes & fees
5/10 (1,021 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
Sonesta Select Newark Christiana Mall, located 11.6 mi (18.7 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Quality Inn Newark - Wilmington and DoubleTree by Hilton Downtown Wilmington - Legal District. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: Visitors like this Winchester vacation home rental. It 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. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For additional details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
What is staying in Winchester like?
Visitors are sure to enjoy all that Winchester has to offer. There are 639 hotels and other accommodations in the surrounding area. Find out more about Winchester.
What should I see while I'm in Winchester?
Places to visit in the wider area include Fair Hill State Natural Resources Management Area, University of Delaware Botanic Gardens, and Bob Carpenter Center. You'll also find Fred Rust Ice Arena and Newark Shopping Center in the area. Check out what more to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 50 inches.

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