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Our top choices for Winchester hotels

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, (975 reviews)
"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"
United States
Carleen Lyden
$51 nightly
The price is $58
Mar 3 - Mar 4
Total with taxes and fees
Super 8 by Wyndham Havre De Grace Aberdeen Area

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (536 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
$133 nightly
The price is $150
Mar 1 - Mar 2
Total with taxes and fees
Vandiver Inn

The Francis Hotel & Suites

The Francis Hotel & Suites
2.0 star property
Kennett Square
10.0 out of 10, Exceptional, (1 review)
"Beautiful new rooms in a cool walkable town. Close to shops, restaurants, and Longwood Gardens "
United States
MICHAEL
$171 nightly
The price is $190
Mar 11 - Mar 12
Total with taxes and fees
The Francis Hotel & Suites

The Bookhouse Hotel

The Bookhouse Hotel
2.0 star property
Kennett Square
9.6 out of 10, Exceptional, (45 reviews)
"Outstanding! Great Location, awesome room and extremely comfy bed!"
United States
John
$189 nightly
The price is $210
Mar 4 - Mar 5
Total with taxes and fees
The Bookhouse Hotel

Miller-Dunham House Bed & Breakfast

Miller-Dunham House Bed & Breakfast
3.0 star property
Odessa
10.0 out of 10, Exceptional, (86 reviews)
"The Provence room was beautiful, Heather and TJ were very warm and friendly. Everything was exceptionally clean. No complaints. "
United States
Matthew
$236 nightly
The price is $247
Mar 1 - Mar 2
Total with taxes and fees
Miller-Dunham House Bed & Breakfast

Artelo

Artelo
2.0 star property
Kennett Square
9.8 out of 10, Exceptional, (101 reviews)
"Great place "
United States
Justin
$133 nightly
The price is $148
Mar 12 - Mar 13
Total with taxes and fees
Artelo

Pleasant Hill Motel

Pleasant Hill Motel
2.5 star property
Middletown
7.2 out of 10, Good, (170 reviews)
"Front desk was great room was very clean will stay here again"
United States
Wayne Mark
$82 nightly
The price is $91
Mar 2 - Mar 3
Total with taxes and fees
Pleasant Hill Motel

Comfort Inn & Suites North East

Comfort Inn & Suites North East
2.5 star property
North East
7.8 out of 10, Good, (662 reviews)
"Great stay"
United States
Tina
$82 nightly
The price is $91
Mar 3 - Mar 4
Total with taxes and fees
Comfort Inn & Suites North East

Wingate by Wyndham North East

Wingate by Wyndham North East
2.5 star property
North East
8.0 out of 10, Very Good, (960 reviews)
"Good stay. The room was clean, bed was super comfortable and the shower was great. "
United States
DeAnda
$98 nightly
The price is $110
Mar 2 - Mar 3
Total with taxes and fees
Wingate by Wyndham North East

Hilton Garden Inn Kennett Square

Hilton Garden Inn Kennett Square
3.0 star property
Kennett Square
8.4 out of 10, Very Good, (953 reviews)
"Excellent accommodations "
United States
pat
$114 nightly
The price is $127
Mar 8 - Mar 9
Total with taxes and fees
Hilton Garden Inn Kennett Square

Red Carpet Inn

Red Carpet Inn
2.0 star property
Elkton
6.4 out of 10, (458 reviews)
"Room was clean and the price was reasonable. "
United States
Jared
$73 nightly
The price is $82
Mar 2 - Mar 3
Total with taxes and fees
Red Carpet Inn

Travelodge by Wyndham Elkton University Area

Travelodge by Wyndham Elkton University Area
2.0 star property
Elkton
5.2 out of 10, (502 reviews)
"Love the location "
United States
Mark
$62 nightly
The price is $70
Mar 6 - Mar 7
Total with taxes and fees
Travelodge by Wyndham Elkton University Area

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, (1,001 reviews)
"Spotless room, friendly staff, good coffee and breakfast"
United States
Deborah
$127 nightly
The price is $141
Mar 8 - Mar 9
Total with taxes and fees
Fairfield Inn by Marriott Kennett Square Brandywine Valley

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, (559 reviews)
"The room was clean and the staff was friendly and helpful."
United States
Mary Jane
$89 nightly
The price is $100
Mar 3 - Mar 4
Total with taxes and fees
Holiday Inn Express North East by IHG

Elk Forge B&B Inn & Day Spa

Elk Forge B&B Inn & Day Spa
2.5 star property
Elkton
8.8 out of 10, Excellent, (190 reviews)
"A beautiful little B&B, provides a snapshot of yesteryear and I appreciate that. Room was clean, and the surrounding area is absolutely beautiful, with a park nearby for walks. "
United States
Sarah
$129 nightly
The price is $137
Mar 1 - Mar 2
Total with taxes and fees
Elk Forge B&B Inn & Day Spa

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (880 reviews)
"Clean room.breakfast was great.Staff.was helpful."
United States
Susan
$95 nightly
The price is $106
Mar 9 - Mar 10
Total with taxes and fees
Hampton Inn Middletown

Residence Inn by Marriott Newark, DE

Residence Inn by Marriott Newark, DE
3.0 star property
Newark
8.8 out of 10, Excellent, (26 reviews)
"all aspects of this facility were wonderful from the room to staff breakfast all top of the line thank you "
United States
Bret
$110 nightly
The price is $122
Mar 22 - Mar 23
Total with taxes and fees
Residence Inn by Marriott Newark, DE

Motel 6 Elkton, MD

Motel 6 Elkton, MD
2.0 star property
Elkton
6.0 out of 10, (1,000 reviews)
"They have created a well lit motel that feels very safe."
United States
Daniel
$70 nightly
The price is $78
Mar 1 - Mar 2
Total with taxes and fees
Motel 6 Elkton, MD

Elkton Lodge - Newark - Elkton - University Gateway

Elkton Lodge - Newark - Elkton - University Gateway
2.0 star property
Elkton
8.6 out of 10, Excellent, (27 reviews)
"Affordable clean place to stay. "
United States
Christa
$78 nightly
The price is $88
Mar 2 - Mar 3
Total with taxes and fees
Elkton Lodge - Newark - Elkton - University Gateway

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington
3.0 star property
Newark
7.0 out of 10, Good, (1,002 reviews)
"very friendly and helpful staff"
United States
Gary L.
$79 nightly
The price is $88
Mar 30 - Mar 31
Total with taxes and fees
Ramada by Wyndham Newark/Wilmington
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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Hotels in Winchester with star-rating

Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the historic downtown, which is the heart of the city and offers a blend of history and convenience.

This area is highly walkable and characterized by its unique architecture and tree-lined streets. You'll find many local shops, restaurants, and historical markers along the Loudoun Street Walking Mall, a pedestrian-only thoroughfare. The area is also home to landmarks like the Handley Regional Library and the Old Court House Civil War Museum.

Couples will find downtown Winchester particularly appealing for a relaxing getaway. The pedestrian mall provides a pleasant setting for strolls, and there are many dining options from casual eateries to upscale restaurants. The proximity to historical sites and local boutiques makes it easy to fill a day with activities without needing a car.

For those interested in history, staying downtown provides direct access to Winchester's rich past.
When is the best time to go to Winchester?
The best time to visit Winchester, Maryland, is during the spring and fall months, specifically from April to May and September to October. These periods offer pleasant weather conditions that are ideal for exploring the area's attractions.

Spring brings blooming flowers and comfortable temperatures, great for outdoor activities like walking tours of the historic downtown or visiting nearby orchards. The average daytime temperatures range from the low 60s to mid-70s Fahrenheit, making it enjoyable to spend time outside without extreme heat or cold.

Fall provides crisp air, colorful foliage, and a variety of harvest-themed events. Temperatures typically range from the mid-50s to upper 60s Fahrenheit. This season is particularly appealing for couples looking for scenic drives through the Shenandoah Valley or visiting local wineries and cideries.
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?
With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $58 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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