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Sep 27 - Sep 28
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Sep 28 - Sep 29
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Oct 2 - Oct 4
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Our top choices for Winchester hotels

A swimming pool with a water slide and a lifeguard stand.
A spacious indoor area with a central staircase, a flat-screen TV, and a wall with framed pictures.
A modern interior with a fireplace, a balcony, and a wall-mounted picture.
A reception area with a counter, an exit sign, a staircase, and a wall with a kitchen-themed mural.

1. Dutch Wonderland Inn

Dutch Wonderland Inn
Dutch Countryside
United States
Renee
$95 nightly
$105 total
Sep 28 - Sep 29
Total with taxes and fees
Dutch Wonderland Inn
A living room with a fireplace, leather sofa, patterned armchair, and a blue shelving unit.
A hotel room with a large bed, a red armchair, a small desk, a bathroom with a bathtub, and a TV.
A hotel entrance with a covered walkway, a parking lot, and a tree in the foreground.
A swimming pool with a tiled deck, a lounge area with chairs, and large windows offering a view of the outdoors.

2. Parkview Inn & Suites Lancaster

Parkview Inn & Suites Lancaster
Dutch Countryside
United States
Marie
$102 nightly
$113 total
Oct 25 - Oct 26
Total with taxes and fees
Parkview Inn & Suites Lancaster
A multi-level hotel lobby with a central water feature, seating areas, and a reception desk.
A multi-story hotel with a central entrance, large windows, and a well-lit facade.
A spacious indoor area with multiple levels, wooden pergola structures, and a variety of seating arrangements including tables and chairs.
A multi-level hotel atrium with balconies, seating areas, and a central water feature.

3. Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South
Newark
United States
Walter
$106 nightly
$117 total
Oct 25 - Oct 26
Total with taxes and fees
Embassy Suites by Hilton Newark Wilmington South
An indoor water park with multiple slides, a water fountain, and seating areas.
A spacious lobby with a large stone fireplace, modern seating, and large windows with forest views.
An indoor adventure park with rope bridges, climbing structures, and artificial trees.
An indoor play area with climbing structures, artificial trees, and a sign reading "Howlin' One."

4. Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
Perryville
United States
Kishana
$207 nightly
$232 total
Sep 28 - Sep 29
Total with taxes and fees
Great Wolf Lodge Perryville
A lobby with seating, a reception desk, and a cityscape mural on the wall.
A spacious indoor area with multiple seating options including tables and booths, a bar area with a cityscape mural, and large windows providing natural light.
A hotel room with a bed, a sofa, a small table, a TV, and a framed picture on the wall.
A swimming pool with a blue interior, surrounded by lounge chairs and a changing area.

5. La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton
Elkton
United States
Donnie
$103 nightly
$116 total
Oct 4 - Oct 5
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Newark - Elkton
A breakfast buffet area with a refrigerated display case, various food stations, and wall-mounted light fixtures.
A modern living room with a sofa, ottoman, fireplace, and a TV mounted on the wall.
A hotel room with two beds, each with white linens and a red throw blanket. There are wall-mounted lamps and a window with a view.
A reception desk with a computer, a chair, and a window with a view of a silo.

6. Comfort Inn Lancaster at Rockvale

Comfort Inn Lancaster at Rockvale
Dutch Countryside
United States
ann marie
$100 nightly
$111 total
Oct 26 - Oct 27
Total with taxes and fees
Comfort Inn Lancaster at Rockvale
A hotel lobby with a reception desk, a blue sofa, a staircase, and a wooden floor.
A modern living room with a blue sofa, a yellow armchair, and a small round table. Adjacent to the living room is a kitchen with dark cabinets and a blue wall.
A hotel dining area with multiple tables and chairs, a flat-screen TV on the wall, and a door on the right.
A Baymont Inn & Suites building with a stone facade, large entrance, and a clear blue sky.

7. Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware
Newark
United States
Brian
$81 nightly
$90 total
Oct 5 - Oct 6
Total with taxes and fees
Baymont by Wyndham Newark at University of Delaware
Casey Jones' Restaurant with a long, narrow dining area featuring rows of tables and chairs.
A bedroom with a bed, a desk, two chairs, a round table, and a window with blinds.
A yellow train car with a black door, a picnic table, and a wooden fence in a grassy area with trees.
A compact living space with a sofa, a small table, a lamp, a ceiling fan, a kitchenette, and a door leading to another room.

8. Red Caboose Motel

Red Caboose Motel
Ronks
United States
Olga
$110 nightly
$122 total
Oct 5 - Oct 6
Total with taxes and fees
Red Caboose Motel
A spacious lobby with a central seating area, a reception desk, and a chandelier.
A terrace with white plastic chairs and tables, a red umbrella, and a white picket fence.
A hotel room with a large bed, a desk, a chair, and a sofa.
A spacious living area with a sofa, armchairs, a coffee table, and a patterned rug.

9. La Quinta Inn & Suites by Wyndham Lancaster

La Quinta Inn & Suites by Wyndham Lancaster
Dutch Countryside
United States
Katayoon
$99 nightly
$109 total
Oct 25 - Oct 26
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lancaster
A serene pond with ducks, surrounded by lush greenery and a gazebo.
A pool area with lounge chairs and tables, surrounded by large windows and potted plants.
A hotel room with a large bed, a nightstand with a lamp, a floral armchair, and a window with curtains.
A playground with a slide, climbing structures, and a small building with a roof.

10. Fulton Steamboat Inn

Fulton Steamboat Inn
Dutch Countryside
United States
Caroline
Fulton Steamboat Inn
An outdoor seating area with fire pits, umbrellas, and modern furniture.
A modern bar area with multiple seating options, including bar stools and cushioned chairs, and a television mounted on the wall.
A modern indoor pool area with a clear view through large windows, a pool with a blue tiled edge, and a seating area with chairs and a table.
A modern dining area with long wooden tables and leather chairs, large windows, and a brick wall.

11. Hyatt Place Newark - Main Street

Hyatt Place Newark - Main Street
Newark
United States
Sheri
$161 nightly
$179 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Newark - Main Street
A modern kitchen with dark cabinetry, a large island, and a black backsplash with 'EAT' and food-related graphics.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.
An indoor swimming pool with clear blue water, a sunroof, and lounge chairs.
A modern reception area with a reception desk, a welcome sign, a refrigerator with beverages, and a view through large glass doors.

12. Hampton Inn Elkton

Hampton Inn Elkton
Elkton
United States
Cathy
$98 nightly
$109 total
Oct 18 - Oct 19
Total with taxes and fees
Hampton Inn Elkton
A row of houses with stone facades, white railings, and outdoor seating areas.
A fireplace with a TV mounted above it displaying a welcome message. A Christmas tree is visible in the background.
A hot tub with a tiled edge and a view of the outdoors through large windows.
A living room with a fireplace, a television mounted above it, and a small table with a vase of flowers.

13. Bird in Hand Family Inn

Bird in Hand Family Inn
Bird In Hand
United States
Dennis
$116 nightly
$129 total
Oct 26 - Oct 27
Total with taxes and fees
Bird in Hand Family Inn
A lobby with a curved floor, a reception desk, and seating areas.
A hotel room with a red sofa, two beds, a desk with a computer, a TV, and a large window with curtains.
A conference room with rows of chairs, a podium, and a Holiday Inn Express sign.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.

14. Holiday Inn Express & Suites Elkton - University Area by IHG

Holiday Inn Express & Suites Elkton - University Area by IHG
Elkton
United States
Heather
$120 nightly
$134 total
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Express & Suites Elkton - University Area by IHG
A DoubleTree by Hilton hotel with a brick facade, large windows, and a covered entrance area.
A gym with cardio machines, weightlifting equipment, and a wall-mounted TV.
A banquet hall with round tables set for dining, featuring black tablecloths and silver sashes.
A conference room with rows of chairs, a projector screen, and a carpeted floor.

15. DoubleTree by Hilton Hotel Wilmington

DoubleTree by Hilton Hotel Wilmington
Wilmington
United States
Deborah
$114 nightly
$127 total
Oct 18 - Oct 19
Total with taxes and fees
DoubleTree by Hilton Hotel Wilmington
A modern kitchen area with a counter, seating, and a coffee machine.
A hotel room with two beds, a desk, and a chair. There are framed artworks on the wall and a window with curtains.
A modern hotel reception desk with a vertical wood panel design, a digital screen, and a reception counter.
A modern hotel lobby with a central seating area, a flat-screen TV mounted on the wall, and large windows with curtains.

16. Spark by Hilton Exton

Spark by Hilton Exton
Exton
United States
Kenneth and Christine
$68 nightly
$76 total
Oct 27 - Oct 28
Total with taxes and fees
Spark by Hilton Exton
An indoor pool with wooden beams, tiled walls, and sunlit windows.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A hotel lobby with a reception desk, seating area, and a kitchenette.
A hotel lobby with a brick fireplace, seating area, and a flat-screen TV mounted on the wall.

17. Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn
Bear
United States
Fred
$89 nightly
$99 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Plus Newark/Christiana Inn
A hotel room with a large bed, two bedside lamps, a nightstand, a chair, and a wooden table.
A building with a sign reading 'Elkton Lodge' and a 'Lobby' sign.
A motel with a parking lot, a landscaped area with flowers, and a sign reading 'ELKTON LODGE.'
A reception desk with a Buddha statue, a framed photo, and a vase of flowers.

18. Elkton Lodge - Newark - Elkton - University Gateway

Elkton Lodge - Newark - Elkton - University Gateway
Elkton
United States
Joseph
$107 nightly
$120 total
Sep 29 - Sep 30
Total with taxes and fees
Elkton Lodge - Newark - Elkton - University Gateway
A modern bar area with a wooden ceiling, a television screen, and a bar stocked with various bottles. There are several wooden tables and chairs arranged for dining.
A hotel room with a bed, a desk, a TV mounted on the wall, and a bathroom visible through an open door.
A modern building with large windows and two white planters with flowers.
A clean, modern kitchenette with a refrigerator, microwave, and pantry stocked with snacks and beverages.

19. SpringHill Suites by Marriott Newark Downtown

SpringHill Suites by Marriott Newark Downtown
Newark
United States
Sharon
$151 nightly
$167 total
Oct 4 - Oct 5
Total with taxes and fees
SpringHill Suites by Marriott Newark Downtown
A circular stone fire pit surrounded by wicker furniture and a sofa, with a building in the background.
A modern living room with a fireplace, sofas, armchairs, and a flat-screen TV.
A display of snack and microwave products in a store.
A hotel bathroom with a large mirror, a microwave, and a coffee maker on the countertop.

20. Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall
Newark
United States
Gale
$93 nightly
$103 total
Sep 29 - Sep 30
Total with taxes and fees
Sonesta Select Newark Christiana Mall
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Top Winchester Hotel Reviews

Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG

10/10 Excellent
"4th stay. Neat, clean, accessible."
Lawrence B 2-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Wilmington-Newark by IHG
Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

8/10 Good
"It’s was ok,"
Grzegorz 1-night trip
Posted 2 days ago
Baymont by Wyndham Newark at University of Delaware
La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton

8/10 Good
"Lovelybreakfast. Clean pool. Well furnished room. Complimentary beverages round the clock. Only problem is the noise from the adjoining highways and roads, disturbing my sleep. Luckily I was moved to another room that was quiet"
Olanrewaju 4-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Newark - Elkton
Red Roof Inn Perryville

Red Roof Inn Perryville

10/10 Excellent
"Word Word word"
Roy 2-night trip
Posted 2 days ago
Red Roof Inn Perryville
Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

10/10 Excellent
"Every thing was good except for cleanliness .my sheet had a brown stain"
Lawrence 1-night trip
Posted 3 days ago
Ramada by Wyndham Newark/Wilmington
DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

8/10 Good
"Comfortable hotel an easy walk from the centre of Wilmington."
John 2-night trip
Posted 4 days ago
DoubleTree by Hilton Downtown Wilmington - Legal District
Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

10/10 Excellent
"This hotel was all that I was expecting it to be from the reviews I read online."
Jennifer Monique 3-night trip
Posted 5 days ago
Sheraton Suites Wilmington Downtown

More cheap stays in Winchester

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE
$68 nightly
$76 total
Oct 28 - Oct 29
Total with taxes and fees
6.2/10 (1,006 reviews)
Quality Inn Newark - Wilmington
Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

1119 S College Avenue Newark DE
$69 nightly
$77 total
Sep 28 - Sep 29
Total with taxes and fees
Red Roof Inn & Suites Newark - University
Red Roof Inn Perryville

Red Roof Inn Perryville

61 Heather Lane Perryville MD
$74 nightly
$83 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (241 reviews)
Red Roof Inn Perryville
Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

630 S College Ave Newark DE
$81 nightly
$90 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Baymont by Wyndham Newark at University of Delaware
Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE
$89 nightly
$99 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Plus Newark/Christiana Inn
Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE
$94 nightly
$103 total
Sep 28 - Sep 29
Total with taxes and fees
Woodspring Suites Wilmington Riverfront

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 much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $63 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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