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Oct 19 - Oct 20
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Our top choices for Winchester hotels

A swimming pool with a water slide and a lifeguard stand.
A restaurant with long tables, a TV screen, and a market area.
A spacious indoor area with a central staircase, a flat-screen TV, and a wall with framed pictures.
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
Jason
$109 nightly
$121 total
Nov 11 - Nov 12
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 gym with treadmills, an elliptical, and a stationary bike.
A hotel entrance with a covered walkway, a parking lot, and a tree in the foreground.

2. Parkview Inn & Suites Lancaster

Parkview Inn & Suites Lancaster
Dutch Countryside
United States
Joy
$105 nightly
$117 total
Nov 15 - Nov 16
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 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 a central open space, seating areas, and balconies with greenery.
A modern hotel room with a grey sofa, a small table, and a dining area with chairs.

3. Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South
Newark
United States
Victoria
$118 nightly
$131 total
Nov 8 - Nov 9
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.
An indoor play area with climbing structures, artificial trees, and a sign reading "Howlin' One."
A restaurant with multiple tables and chairs, a sign reading "Campfire Kitchen", and a large tree in the center.
A spacious lobby with a large stone fireplace, modern seating, and large windows with forest views.

4. Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
Perryville
United States
Shatana
$207 nightly
$232 total
Oct 20 - Oct 21
Total with taxes and fees
Great Wolf Lodge Perryville
A lobby with seating, a reception desk, and a cityscape mural on the wall.
A hotel room with a bed, a sofa, a small table, a TV, and a framed picture on the wall.
A hotel room with a desk, chair, sofa, and a TV. There are framed pictures on the wall and a window with curtains.
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
David
$106 nightly
$119 total
Nov 1 - Nov 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Newark - Elkton
A hotel lobby with a reception desk, a blue sofa, a staircase, and a wooden floor.
A Baymont Inn & Suites building with a stone facade, large entrance, and a clear blue sky.
A hotel dining area with multiple tables and chairs, a flat-screen TV on the wall, and a door on the right.
A hotel room with a bed, a desk with a TV, a chair, a couch, and a window with curtains.

6. Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware
Newark
United States
Jean
$85 nightly
$94 total
Oct 25 - Oct 26
Total with taxes and fees
Baymont by Wyndham Newark at University of Delaware
A spacious lobby with a central seating area, a reception desk, and a chandelier.
A hotel lobby with a reception desk, a coffee station, and a seating area with a table and chairs.
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.

7. La Quinta Inn & Suites by Wyndham Lancaster

La Quinta Inn & Suites by Wyndham Lancaster
Dutch Countryside
United States
Sarah
$88 nightly
$97 total
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lancaster
A modern kitchen with dark cabinetry, a large island, and a black backsplash with 'EAT' and food-related graphics.
A modern reception area with a reception desk, a welcome sign, a refrigerator with beverages, and a view through large glass doors.
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.

8. Hampton Inn Elkton

Hampton Inn Elkton
Elkton
United States
Katherine
$105 nightly
$118 total
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn Elkton
Casey Jones' Restaurant with a long, narrow dining area featuring rows of tables and chairs.
A yellow train car with a black door, a picnic table, and a wooden fence in a grassy area with trees.
A bedroom with a bed, a desk, two chairs, a round table, and a window with blinds.
A restaurant with a long, curved ceiling lined with hanging lights, tables and chairs arranged in rows, and a central aisle leading to a door.

9. Red Caboose Motel

Red Caboose Motel
Ronks
United States
Donna
$110 nightly
$122 total
Nov 2 - Nov 3
Total with taxes and fees
Red Caboose Motel
A serene pond with ducks, surrounded by lush greenery and a gazebo.
A hotel room with a large bed, a nightstand with a lamp, a floral armchair, and a window with curtains.
A bar area with wooden tables and chairs, a bar counter with bottles, and a ship's wheel on the wall.
A pool area with lounge chairs and tables, surrounded by large windows and potted plants.

10. Fulton Steamboat Inn

Fulton Steamboat Inn
Dutch Countryside
United States
DESIREE
$268 nightly
$297 total
Nov 14 - Nov 15
Total with taxes and fees
Fulton Steamboat Inn
A lobby with a curved floor, a reception desk, and seating areas.
A modern lobby with a large wall map, seating areas, and a reception desk.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.
A hotel room with a red sofa, two beds, a desk with a computer, a TV, and a large window with curtains.

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

Holiday Inn Express & Suites Elkton - University Area by IHG
Elkton
United States
Cynthia
$120 nightly
$134 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express & Suites Elkton - University Area by IHG
An outdoor seating area with fire pits, umbrellas, and modern furniture.
A modern lobby with a wooden ceiling, a large TV, comfortable seating, and a reception desk.
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.

12. Hyatt Place Newark - Main Street

Hyatt Place Newark - Main Street
Newark
United States
Vilma
$156 nightly
$173 total
Nov 1 - Nov 2
Total with taxes and fees
Hyatt Place Newark - Main Street
A breakfast buffet area with a refrigerated display case, various food stations, and wall-mounted light fixtures.
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 hotel lobby with a reception desk, seating area, and a fireplace.
A reception desk with a computer, a chair, and a window with a view of a silo.

13. Comfort Inn Lancaster at Rockvale

Comfort Inn Lancaster at Rockvale
Dutch Countryside
United States
Karri
$93 nightly
$103 total
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn Lancaster at Rockvale
A hotel room with a dining area, a sofa, a TV, and a view of the outdoors.
A DoubleTree by Hilton hotel with a brick facade, large windows, and a covered entrance area.
A banquet hall with round tables set for dining, featuring black tablecloths and silver sashes.
A hotel room with two beds, a desk, a TV, and a window with a view.

14. DoubleTree by Hilton Hotel Wilmington

DoubleTree by Hilton Hotel Wilmington
Wilmington
United States
Lisa
$127 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
DoubleTree by Hilton Hotel Wilmington
A hotel room with a large bed, two bedside lamps, a nightstand, a chair, and a wooden table.
A view from a balcony with a metal railing, a parking lot, and a building with a McDonald's sign in the background.
A reception desk with a Buddha statue, a framed photo, and a vase of flowers.
A building with a sign reading 'Elkton Lodge' and a 'Lobby' sign.

15. Elkton Lodge - Newark - Elkton - University Gateway

Elkton Lodge - Newark - Elkton - University Gateway
Elkton
United States
Joseph
$119 nightly
$133 total
Oct 20 - Oct 21
Total with taxes and fees
Elkton Lodge - Newark - Elkton - University Gateway
A row of houses with stone facades, white railings, and outdoor seating areas.
A buffet with various food items and serving utensils.
A living room with a fireplace, a television mounted above it, and a small table with a vase of flowers.
A fireplace with a TV mounted above it displaying a welcome message. A Christmas tree is visible in the background.

16. Bird in Hand Family Inn

Bird in Hand Family Inn
Bird In Hand
United States
Kathleen
$116 nightly
$129 total
Oct 26 - Oct 27
Total with taxes and fees
Bird in Hand Family Inn
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 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.
A hotel room with a bed, a desk, a TV mounted on the wall, and a bathroom visible through an open door.

17. SpringHill Suites by Marriott Newark Downtown

SpringHill Suites by Marriott Newark Downtown
Newark
United States
Sharon
$151 nightly
$167 total
Oct 25 - Oct 26
Total with taxes and fees
SpringHill Suites by Marriott Newark Downtown
An indoor swimming pool with clear water, surrounded by glass walls and a tiled floor.
A hotel kitchen with a buffet setup, including a fruit display and a beverage station.
A spacious lobby with a brick fireplace, wicker furniture, and a patterned rug.
A gym with treadmills, stationary bikes, and dumbbells.

18. Homewood Suites by Hilton Newark-Wilmington South Area

Homewood Suites by Hilton Newark-Wilmington South Area
Newark
United States
leslie
$105 nightly
$117 total
Nov 2 - Nov 3
Total with taxes and fees
Homewood Suites by Hilton Newark-Wilmington South Area
A hotel room with a large bathtub filled with water and rose petals, a sofa, a lamp, and a window with blinds.
A room with a checkered floor, black and white chairs, a fountain, and a stained glass window.
A view from a window with a wooden deck and greenery outside.
A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn with trees.

19. Elk Forge B&B Inn & Day Spa

Elk Forge B&B Inn & Day Spa
Elkton
United States
Denise
$129 nightly
$137 total
Oct 20 - Oct 21
Total with taxes and fees
Elk Forge B&B Inn & Day Spa
A circular stone fire pit surrounded by wicker furniture and a sofa, with a building in the background.
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.
A modern living room with a fireplace, sofas, armchairs, and a flat-screen TV.

20. Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall
Newark
United States
christyann
$127 nightly
$141 total
Oct 20 - Oct 21
Total with taxes and fees
Sonesta Select Newark Christiana Mall
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Top Winchester Hotel Reviews

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

8/10 Good
"Staff was awesome. Hotel is a little old and needs some upgrades but it was clean, quiet and in a safe neighborhood."
Marilyn 1-night trip
Posted 9 hours ago
Ramada by Wyndham Newark/Wilmington
Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent
"We have stayed at this hotel for Bands of America competition three years in a row now and God willing will do so again next October. Staff is friendly and helpful. Rooms are clean. The breakfast is very good."
Kenneth 2-night trip
Posted 10 hours ago
Comfort Inn & Suites Newark - Wilmington
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

8/10 Good
"staff was friendly and helpful… facility was clean…limited parking - needed to park in the lot next to the Sonesta"
christyann 2-night trip
Posted 10 hours ago
Sonesta Select Newark Christiana Mall
Travel Inn

Travel Inn

10/10 Excellent
"This has always been a great place to stay and continues to get better. My preferred place to stay when I’m in New Castle, DE"
Hector 1-night trip
Posted 10 hours ago
Travel Inn
Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

8/10 Good
"It was a little expensive but two nice rooms and nice shower."
David 1-night trip
Posted 16 hours ago
Sheraton Suites Wilmington Downtown
Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

8/10 Good
"Included breakfast was good and the location across the street from the UDel stadium was great. My only complaint is that there are no hooks to hang towels in the bathroom or by the sink."
Shellie 2-night trip
Posted 17 hours 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

10/10 Excellent
"Great hotel for the price!! Wonderful staff. Clean property. I forgot a couple things in the room and they called me twice! Breakfast was simple but good."
Beth 2-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Newark - Elkton

More cheap stays in Winchester

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE
$66 nightly
$74 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Newark - Wilmington
Red Roof Inn Perryville

Red Roof Inn Perryville

61 Heather Lane Perryville MD
$67 nightly
$75 total
Nov 8 - Nov 9
Total with taxes and fees
Red Roof Inn Perryville
Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

1119 S College Avenue Newark DE
$74 nightly
$82 total
Oct 20 - Oct 21
Total with taxes and fees
5.6/10 (1,002 reviews)
Red Roof Inn & Suites Newark - University
Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

630 S College Ave Newark DE
$85 nightly
$94 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
Baymont by Wyndham Newark at University of Delaware
Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE
$94 nightly
$103 total
Oct 25 - Oct 26
Total with taxes and fees
Woodspring Suites Wilmington Riverfront
Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE
Get ratesBest Western Plus Newark/Christiana Inn

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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