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Our top choices for Winchester hotels

Red Roof Inn Perryville

Red Roof Inn Perryville
2.0 star property
Perryville
9.0 out of 10, Wonderful, (197 reviews)
"Clean and perfect for one night stay. Would stay again!"
United States
Andrea
The price is CA $106
CA $119 total
includes taxes & fees
Jun 29 - Jun 30
Red Roof Inn Perryville

Residence Inn By Marriott Wilmington

Residence Inn By Marriott Wilmington
3.0 star property
Wilmington
The price is CA $276
CA $306 total
includes taxes & fees
Jun 29 - Jun 30
Residence Inn By Marriott Wilmington

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, (1,003 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
The price is CA $78
CA $87 total
includes taxes & fees
Jun 28 - Jun 29
Super 8 by Wyndham Havre De Grace Aberdeen Area

Artelo

Artelo
2.0 star property
Kennett Square
9.8 out of 10, Exceptional, (138 reviews)
"Love the art work and the location!! Very clean and comfortable room 👌"
United States
Jacqueline
The price is CA $178
CA $197 total
includes taxes & fees
Jun 28 - Jun 29
Artelo

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington
3.0 star property
Newark
7.2 out of 10, Good, (1,004 reviews)
"It was clean, breakfast was good, and good value. "
United States
George
The price is CA $98
CA $109 total
includes taxes & fees
Jul 6 - Jul 7
Ramada by Wyndham Newark/Wilmington

Wingate by Wyndham North East

Wingate by Wyndham North East
3.0 star property
North East
8.2 out of 10, Very good, (1,002 reviews)
"Great staff, clean rooms, and great breakfast options!"
United States
Aidan
The price is CA $130
CA $146 total
includes taxes & fees
Jul 19 - Jul 20
Wingate by Wyndham North East

The Bookhouse Hotel

The Bookhouse Hotel
2.0 star property
Kennett Square
9.6 out of 10, Exceptional, (52 reviews)
"Very nice place to stay."
United States
Kevin
The price is CA $259
CA $311 total
includes taxes & fees
Jul 7 - Jul 8
The Bookhouse Hotel

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn
2.5 star property
Bear
8.2 out of 10, Very good, (334 reviews)
"Great place to stay"
United States
Nysier
The price is CA $118
CA $131 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Plus Newark/Christiana Inn

Elkton Lodge - Newark - Elkton - University Gateway

Elkton Lodge - Newark - Elkton - University Gateway
2.0 star property
Elkton
8.6 out of 10, Excellent, (44 reviews)
"Room was exactly as advertised. Right economic choice for our 1 night stay."
United States
John
The price is CA $104
CA $139 total
includes taxes & fees
Jul 6 - Jul 7
Elkton Lodge - Newark - Elkton - University Gateway

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware
2.5 star property
Newark
8.0 out of 10, Very good, (1,004 reviews)
"Room was clean, it was quiet, staff was friendly and knowledgeable about places and suggested places to eat and explore."
United States
Michelle
The price is CA $112
CA $124 total
includes taxes & fees
Jul 1 - Jul 2
Baymont by Wyndham Newark at University of Delaware

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
2.0 star property
Perryville
8.8 out of 10, Excellent, (241 reviews)
"Great place to visit was the perfect getaway with the family!!!"
United States
Crystal
The price is CA $253
CA $284 total
includes taxes & fees
Jul 5 - Jul 6
Great Wolf Lodge Perryville

Days Inn by Wyndham Newark Wilmington

Days Inn by Wyndham Newark Wilmington
2.0 star property
Newark
5.8 out of 10, (1,005 reviews)
"Limited breakfast."
United States
Marilyn
The price is CA $90
CA $100 total
includes taxes & fees
Jul 1 - Jul 2
Days Inn by Wyndham Newark Wilmington

Pleasant Hill Motel

Pleasant Hill Motel
2.5 star property
Middletown
7.2 out of 10, Good, (181 reviews)
"It was a good place to stay for the night."
United States
Ed
The price is CA $101
CA $112 total
includes taxes & fees
Jun 29 - Jun 30
Pleasant Hill Motel

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington
2.5 star property
Newark
9.0 out of 10, Wonderful, (1,125 reviews)
"Quiet, comfortable stay in a spacious room. Good breakfast and amenities, and excellent overall value. Will book again!"
United States
Chris
The price is CA $131
CA $146 total
includes taxes & fees
Jul 13 - Jul 14
Comfort Inn & Suites Newark - Wilmington

Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront
2.5 star property
South Wilmington
8.2 out of 10, Very good, (261 reviews)
"place was clean and amazing definitely would stay here again"
United States
Jean
The price is CA $140
CA $154 total
includes taxes & fees
Jun 28 - Jun 29
Woodspring Suites Wilmington Riverfront

Fairfield Inn by Marriott Kennett Square Brandywine Valley

Fairfield Inn by Marriott Kennett Square Brandywine Valley
3.0 star property
Kennett Square
8.8 out of 10, Excellent, (1,002 reviews)
"Very clean, friendly staff, fresh breakfast"
United States
Roxane
The price is CA $156
CA $173 total
includes taxes & fees
Jul 19 - Jul 20
Fairfield Inn by Marriott Kennett Square Brandywine Valley

Courtyard by Marriott Newark-University of Delaware

Courtyard by Marriott Newark-University of Delaware
3.0 star property
Newark
9.0 out of 10, Wonderful, (579 reviews)
"Our stay was very pleasant. "
United States
Karen
The price is CA $159
CA $176 total
includes taxes & fees
Jun 29 - Jun 30
Courtyard by Marriott Newark-University of Delaware

Inn at Mendenhall

Inn at Mendenhall
4.0 star property
Chadds Ford
9.0 out of 10, Wonderful, (1,003 reviews)
"Would recommend this place"
United States
Kim
The price is CA $169
CA $187 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Mendenhall

Holiday Inn Express & Suites Elkton - University Area by IHG

Holiday Inn Express & Suites Elkton - University Area by IHG
2.5 star property
Elkton
9.2 out of 10, Wonderful, (1,000 reviews)
"The staff went over and above to make my stay enjoyable."
United States
Drew
The price is CA $161
CA $181 total
includes taxes & fees
Jun 28 - Jun 29
Holiday Inn Express & Suites Elkton - University Area by IHG

La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton
3.0 star property
Elkton
9.0 out of 10, Wonderful, (1,003 reviews)
"Affordable, clean, comfortable, friendly staff, basic, perfect place to stay for short visit."
United States
Denise
The price is CA $157
CA $176 total
includes taxes & fees
Jun 29 - Jun 30
La Quinta Inn & Suites by Wyndham Newark - Elkton
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

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Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the historic Old Town, which is the heart of the city and offers a distinctive experience.

Old Town is a very walkable district centred around the Loudoun Street Pedestrian Mall, a brick-paved street closed to vehicle traffic. Here, you'll find a wide selection of independent shops, local restaurants, and historic buildings, including the Handley Regional Library and the Old Court House Civil War Museum. The area retains much of its 18th and 19th-century architecture, providing a pleasant backdrop for a stroll.

Couples often find Old Town ideal for a romantic getaway. The evening atmosphere is particularly pleasant, with many restaurants offering outdoor seating and the pedestrian mall providing a charming setting for an evening walk. You're also close to several historic sites, such as George Washington's Office Museum.

Solo travellers looking for convenience and a sense of place will also appreciate Old Town. Everything you need is within easy reach, from coffee shops for a morning pick-me-up to cultural attractions, all accessible on foot.
When is the best time to go to Winchester?
The best areas to stay in Winchester are the historic downtown district and the area around Apple Blossom Mall for convenience.

The historic downtown is ideal for those who appreciate history and being able to walk to attractions. This area is centred around the Old Town Walking Mall, a pedestrian-only zone lined with boutiques, restaurants, and historic buildings. You'll find landmarks like the Handley Regional Library and the Winchester-Frederick County Historical Society nearby. The streets are generally well-maintained and offer a pleasant strolling experience.

Couples often enjoy the downtown area for its romantic charm and access to fine dining and cultural experiences. They can easily spend an evening exploring the shops, enjoying a meal at one of the many independent restaurants, or catching a show at a local theatre.

For families or those looking for modern conveniences and easy access to shopping, the area around Apple Blossom Mall to the west of downtown is a practical choice. Here, you'll find a range of contemporary hotels with amenities like indoor pools and complimentary breakfast. This location provides straightforward access to major roads, making day trips to nearby attractions simple.

Families will appreciate the convenience of having shopping and casual dining options within a short drive.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $87 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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