Top 10 Hotels in Winchester, MD (from $63) 2026 - Competitive Prices

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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 restaurant with long tables, a TV screen, and a market area.

A reception area with a counter, an exit sign, a staircase, and a wall with a kitchen-themed mural.

1. Dutch Wonderland Inn

Dutch Countryside

adriana

$100 nightly

$111 total

Sep 30 - Oct 1

Total with taxes and fees

A living room with a fireplace, leather sofa, patterned armchair, and a blue shelving unit.

A gym with treadmills, an elliptical, and a stationary bike.

A swimming pool with a tiled deck, a lounge area with chairs, and large windows offering a view of the outdoors.

A hotel entrance with a covered walkway, a parking lot, and a tree in the foreground.

2. Parkview Inn & Suites Lancaster

Dutch Countryside

Xaimara

$111 nightly

$123 total

Oct 18 - Oct 19

Total with taxes and fees

A multi-level hotel lobby with a central water feature, seating areas, and a reception desk.

A modern hotel room with a grey sofa, a small table, and a dining area with chairs.

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.

3. Embassy Suites by Hilton Newark Wilmington South

Newark

Walter

$106 nightly

$117 total

Oct 25 - Oct 26

Total with taxes and fees

An indoor water park with multiple slides, a water fountain, and seating areas.

A restaurant with multiple tables and chairs, a sign reading "Campfire Kitchen", and a large tree in the center.

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

Perryville

Kishana

$207 nightly

$232 total

Sep 30 - Oct 1

Total with taxes and fees

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 spacious indoor area with multiple seating options including tables and booths, a bar area with a cityscape mural, and large windows providing natural light.

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

Elkton

Donnie

$103 nightly

$116 total

Oct 4 - Oct 5

Total with taxes and fees

A breakfast buffet area with a refrigerated display case, various food stations, and wall-mounted light fixtures.

A reception desk with a computer, a chair, and a window with a view of a silo.

A hotel lobby with a reception desk, seating area, and a fireplace.

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.

6. Comfort Inn Lancaster at Rockvale

Dutch Countryside

ann marie

$100 nightly

$111 total

Oct 26 - Oct 27

Total with taxes and fees

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 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.

7. Baymont by Wyndham Newark at University of Delaware

Newark

Brian

$81 nightly

$90 total

Oct 5 - Oct 6

Total with taxes and fees

Casey Jones' Restaurant with a long, narrow dining area featuring rows of tables and chairs.

A compact living space with a sofa, a small table, a lamp, a ceiling fan, a kitchenette, and a door leading to another room.

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.

A yellow train car with a black door, a picnic table, and a wooden fence in a grassy area with trees.

8. Red Caboose Motel

Ronks

Olga

$101 nightly

$112 total

Oct 5 - Oct 6

Total with taxes and fees

A spacious lobby with a central seating area, a reception desk, and a chandelier.

A spacious living area with a sofa, armchairs, a coffee table, and a patterned rug.

A hotel room with a large bed, a desk, a chair, and a sofa.

A terrace with white plastic chairs and tables, a red umbrella, and a white picket fence.

9. La Quinta Inn & Suites by Wyndham Lancaster

Dutch Countryside

ELIZABETH

$99 nightly

$109 total

Oct 25 - Oct 26

Total with taxes and fees

A serene pond with ducks, surrounded by lush greenery and a gazebo.

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.

A hotel room with a large bed, a nightstand with a lamp, a floral armchair, and a window with curtains.

10. Fulton Steamboat Inn

Dutch Countryside

Caroline

$145 nightly

$161 total

Oct 4 - Oct 5

Total with taxes and fees

An outdoor seating area with fire pits, umbrellas, and modern furniture.

A modern dining area with long wooden tables and leather chairs, large windows, and a brick 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 bar area with multiple seating options, including bar stools and cushioned chairs, and a television mounted on the wall.

11. Hyatt Place Newark - Main Street

Newark

Sheri

$182 nightly

$202 total

Oct 13 - Oct 14

Total with taxes and fees

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.

An indoor swimming pool with clear blue water, a sunroof, and lounge chairs.

A snack and beverage display area with refrigerated sections and shelves stocked with various snacks and drinks.

12. Hampton Inn Elkton

Elkton

Cathy

$98 nightly

$109 total

Oct 25 - Oct 26

Total with taxes and fees

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 living room with a fireplace, a television mounted above it, and a small table with a vase of flowers.

A hot tub with a tiled edge and a view of the outdoors through large windows.

13. Bird in Hand Family Inn

Bird In Hand

Dennis

$115 nightly

$128 total

Oct 18 - Oct 19

Total with taxes and fees

A lobby with a curved floor, a reception desk, and seating areas.

A conference room with rows of chairs, a podium, and a Holiday Inn Express sign.

A buffet with various food items, including omelets and baked goods, displayed in metal trays.

A hotel room with a red sofa, two beds, a desk with a computer, a TV, and a large window with curtains.

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

Elkton

Heather

$124 nightly

$139 total

Oct 4 - Oct 5

Total with taxes and fees

A DoubleTree by Hilton hotel with a brick facade, large windows, and a covered entrance area.

A hotel room with a large bed, a desk, a chair, a television, and a window with a view of greenery.

A conference room with rows of chairs, a projector screen, and a carpeted floor.

A banquet hall with round tables set for dining, featuring black tablecloths and silver sashes.

15. DoubleTree by Hilton Hotel Wilmington

Wilmington

Deborah

$114 nightly

$127 total

Oct 18 - Oct 19

Total with taxes and fees

A modern kitchen area with a counter, seating, and a coffee machine.

A modern hotel reception desk with a vertical wood panel design, a digital screen, and a reception counter.

A small, well-organized kitchenette with a microwave, a refrigerator, and shelves stocked with snacks and beverages.

A hotel room with two beds, a desk, and a chair. There are framed artworks on the wall and a window with curtains.

16. Spark by Hilton Exton

Exton

Thi Ha Liem

$68 nightly

$76 total

Oct 21 - Oct 22

Total with taxes and fees

An indoor pool with wooden beams, tiled walls, and sunlit windows.

A hotel lobby with a reception desk, seating area, and a kitchenette.

A hotel room with a desk, office chair, sofa, and two lamps.

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

17. Best Western Plus Newark/Christiana Inn

Bear

SIDNEY

$89 nightly

$99 total

Oct 18 - Oct 19

Total with taxes and fees

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 motel with a parking lot, a landscaped area with flowers, and a sign reading 'ELKTON LODGE.'

18. Elkton Lodge - Newark - Elkton - University Gateway

Elkton

Joseph

$100 nightly

$112 total

Sep 30 - Oct 1

Total with taxes and fees

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 clean, modern kitchenette with a refrigerator, microwave, and pantry stocked with snacks and beverages.

A modern building with large windows and two white planters with flowers.

A hotel room with a bed, a desk, a TV mounted on the wall, and a bathroom visible through an open door.

19. SpringHill Suites by Marriott Newark Downtown

Newark

Sharon

$151 nightly

$167 total

Oct 11 - Oct 12

Total with taxes and fees

A circular stone fire pit surrounded by wicker furniture and a sofa, with a building in the background.

A hotel room with a bed, a desk, a chair, a sofa, and a TV.

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

Newark

Gale

$93 nightly

$103 total

Oct 4 - Oct 5

Total with taxes and fees

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Top Winchester Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

8/10 Good

"Toilets backing or leaking."

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent

"The room and rest of the hotel was extremely clean. The people at the front desk were professional and very courteous all the employees are very nice. Everybody said Hello."

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent

"The room was clean and the breakfast was good."

Woodspring Suites Wilmington Riverfront

10/10 Excellent

"The room was nice and very clean. I was disappointed that there were no tissues in the room and the chair was a little uncomfortable. The bed however was very nice."

Red Roof Inn Perryville

8/10 Good

"It was clean, comfortable and economical."

Ramada by Wyndham Newark/Wilmington

10/10 Excellent

"The staff was so nice and helpful"

Best Western Plus Newark/Christiana Inn

10/10 Excellent

"decent stay for the price of the room and plenty of places to eat at in the vacinity"

More cheap stays in Winchester

Red Roof Inn & Suites Newark - University

1119 S College Avenue Newark DE

$69 nightly

$77 total

Sep 30 - Oct 1

Total with taxes and fees

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE

$69 nightly

$77 total

Oct 26 - Oct 27

Total with taxes and fees

Red Roof Inn Perryville

61 Heather Lane Perryville MD

$77 nightly

$86 total

Sep 30 - Oct 1

Total with taxes and fees

8.8/10 Excellent! (242 reviews)

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

Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE

$89 nightly

$99 total

Oct 18 - Oct 19

Total with taxes and fees

8/10 Very Good! (472 reviews)

Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE

$94 nightly

$103 total

Sep 30 - Oct 1

Total with taxes and fees

8.2/10 Very Good! (373 reviews)

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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Lodging

Find hotels in Winchester, MD from $63

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Dutch Wonderland Inn

2. Parkview Inn & Suites Lancaster

3. Embassy Suites by Hilton Newark Wilmington South

4. Great Wolf Lodge Perryville

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

6. Comfort Inn Lancaster at Rockvale

7. Baymont by Wyndham Newark at University of Delaware

8. Red Caboose Motel

9. La Quinta Inn & Suites by Wyndham Lancaster

10. Fulton Steamboat Inn

11. Hyatt Place Newark - Main Street

12. Hampton Inn Elkton

13. Bird in Hand Family Inn

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

15. DoubleTree by Hilton Hotel Wilmington

16. Spark by Hilton Exton

17. Best Western Plus Newark/Christiana Inn

18. Elkton Lodge - Newark - Elkton - University Gateway

19. SpringHill Suites by Marriott Newark Downtown

20. Sonesta Select Newark Christiana Mall

Top Winchester Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

Comfort Inn & Suites Newark - Wilmington

Staybridge Suites Wilmington Downtown by IHG

Woodspring Suites Wilmington Riverfront

Red Roof Inn Perryville

Ramada by Wyndham Newark/Wilmington

Best Western Plus Newark/Christiana Inn

More cheap stays in Winchester

Red Roof Inn & Suites Newark - University

Quality Inn Newark - Wilmington

Red Roof Inn Perryville

Baymont by Wyndham Newark at University of Delaware

Best Western Plus Newark/Christiana Inn

Woodspring Suites Wilmington Riverfront

Hotels in Winchester with star-rating

Frequently asked questions

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