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 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.

A spacious indoor area with a central staircase, a flat-screen TV, and a wall with framed pictures.

1. Dutch Wonderland Inn

Dutch Countryside

Erica

$117 nightly

$130 total

Nov 19 - Nov 20

Total with taxes and fees

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

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.

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

2. Parkview Inn & Suites Lancaster

Dutch Countryside

Joy

$105 nightly

$117 total

Nov 15 - Nov 16

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 spacious indoor area with multiple levels, wooden pergola structures, and a variety of seating arrangements including tables and chairs.

A multi-story hotel with a central entrance, large windows, and a well-lit facade.

3. Embassy Suites by Hilton Newark Wilmington South

Newark

Victoria

$118 nightly

$131 total

Nov 8 - Nov 9

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

Shatana

$207 nightly

$232 total

Oct 22 - Oct 23

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 swimming pool with a blue interior, surrounded by lounge chairs and a changing area.

A hotel room with a desk, chair, sofa, and a TV. There are framed pictures on the wall and a window with curtains.

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

Elkton

Todd

$106 nightly

$119 total

Nov 15 - Nov 16

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 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.

6. Baymont by Wyndham Newark at University of Delaware

Newark

Clinton

$81 nightly

$90 total

Oct 26 - Oct 27

Total with taxes and fees

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

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.

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

7. La Quinta Inn & Suites by Wyndham Lancaster

Dutch Countryside

Francisco

$88 nightly

$97 total

Nov 15 - Nov 16

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.

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

Elkton

Katherine

$105 nightly

$118 total

Nov 15 - Nov 16

Total with taxes and fees

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

Ronks

Donna

$110 nightly

$122 total

Nov 2 - Nov 3

Total with taxes and fees

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

A playground with a slide, climbing structures, and a small building with a roof.

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

Becky

$145 nightly

$161 total

Oct 25 - Oct 26

Total with taxes and fees

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 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.

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

Elkton

Cynthia

$120 nightly

$134 total

Nov 1 - Nov 2

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 lobby with a wooden ceiling, a large TV, comfortable seating, and a reception desk.

12. Hyatt Place Newark - Main Street

Newark

Vilma

$156 nightly

$173 total

Nov 1 - Nov 2

Total with taxes and fees

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 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.

13. Comfort Inn Lancaster at Rockvale

Dutch Countryside

Karri

$93 nightly

$103 total

Nov 15 - Nov 16

Total with taxes and fees

A hotel room with a sofa, a small round table, a TV, a mirror, a lamp, and a bed.

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

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

A hotel room with a bed, a chair, a TV, a window with curtains, and a nightstand with a lamp.

14. DoubleTree by Hilton Hotel Wilmington

Wilmington

Lisa

$127 nightly

$141 total

Oct 29 - Oct 30

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 building with a sign reading 'Elkton Lodge' and a 'Lobby' sign.

A reception desk with a Buddha statue, a framed photo, and a vase of flowers.

15. Elkton Lodge - Newark - Elkton - University Gateway

Elkton

Joseph

$107 nightly

$120 total

Oct 22 - Oct 23

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 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.

16. Bird in Hand Family Inn

Bird In Hand

Kathleen

$117 nightly

$130 total

Oct 26 - Oct 27

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 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

Newark

Sharon

$151 nightly

$167 total

Oct 29 - Oct 30

Total with taxes and fees

An indoor swimming pool with clear water, surrounded by glass walls and a tiled floor.

A gym with treadmills, stationary bikes, and dumbbells.

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.

18. Homewood Suites by Hilton Newark-Wilmington South Area

Newark

leslie

$105 nightly

$117 total

Nov 2 - Nov 3

Total with taxes and fees

A hotel room with a large bathtub filled with water and rose petals, a sofa, a lamp, and a window with blinds.

A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn with trees.

A room with a checkered floor, black and white chairs, a fountain, and a stained glass window.

A room with a bed, a bottle of wine, two glasses, a tray with rose petals, and a painting on the wall.

19. Elk Forge B&B Inn & Day Spa

Elkton

Denise

$129 nightly

$137 total

Oct 22 - Oct 23

Total with taxes and fees

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 hotel bathroom with a large mirror, a microwave, and a coffee maker on the countertop.

A display of snack and microwave products in a store.

20. Sonesta Select Newark Christiana Mall

Newark

Holly

$127 nightly

$141 total

Oct 25 - Oct 26

Total with taxes and fees

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Top Winchester Hotel Reviews

Sonesta ES Suites Wilmington - Newark

8/10 Good

"The room was clean. The air conditioner wasn't the greatest and one of the stairs was loose and almost killed me. But other than that it was fine. Breakfast was good!"

DoubleTree by Hilton Downtown Wilmington - Legal District

10/10 Excellent

"This hotel is being renovated and while this did not really impact our stay, the limited use prevented late checkouts. Nonetheless the aesthetics of the lobby/ chill areas, fresh cookies and excellent sleep quality you're used to getting with Doubletree is still present. I'd come back for sure!!!"

La Quinta Inn & Suites by Wyndham Newark - Elkton

10/10 Excellent

"Room was clean and comfortable."

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent

"This is a grate hotel with grate staff clean! I would definitely stay again!"

Staybridge Suites Wilmington Downtown by IHG

10/10 Excellent

"The place was clean, staff was great & the breakfast options were amazing."

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"

Sheraton Suites Wilmington Downtown

8/10 Good

"It was a little expensive but two nice rooms and nice shower."

More cheap stays in Winchester

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE

$67 nightly

$74 total

Nov 15 - Nov 16

Total with taxes and fees

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 & Suites Newark - University

1119 S College Avenue Newark DE

$74 nightly

$82 total

Oct 22 - Oct 23

Total with taxes and fees

5.6/10 (1,003 reviews)

Baymont by Wyndham Newark at University of Delaware

630 S College Ave Newark DE

$81 nightly

$90 total

Oct 26 - Oct 27

Total with taxes and fees

8.4/10 Very Good! (1,009 reviews)

Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE

$94 nightly

$103 total

Oct 25 - Oct 26

Total with taxes and fees

Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE

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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 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. Baymont by Wyndham Newark at University of Delaware

7. La Quinta Inn & Suites by Wyndham Lancaster

8. Hampton Inn Elkton

9. Red Caboose Motel

10. Fulton Steamboat Inn

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

12. Hyatt Place Newark - Main Street

13. Comfort Inn Lancaster at Rockvale

14. DoubleTree by Hilton Hotel Wilmington

15. Elkton Lodge - Newark - Elkton - University Gateway

16. Bird in Hand Family Inn

17. SpringHill Suites by Marriott Newark Downtown

18. Homewood Suites by Hilton Newark-Wilmington South Area

19. Elk Forge B&B Inn & Day Spa

20. Sonesta Select Newark Christiana Mall

Top Winchester Hotel Reviews

Sonesta ES Suites Wilmington - Newark

DoubleTree by Hilton Downtown Wilmington - Legal District

La Quinta Inn & Suites by Wyndham Newark - Elkton

Baymont by Wyndham Newark at University of Delaware

Staybridge Suites Wilmington Downtown by IHG

Travel Inn

Sheraton Suites Wilmington Downtown

More cheap stays in Winchester

Quality Inn Newark - Wilmington

Red Roof Inn Perryville

Red Roof Inn & Suites Newark - University

Baymont by Wyndham Newark at University of Delaware

Woodspring Suites Wilmington Riverfront

Best Western Plus Newark/Christiana Inn

Hotels in Winchester with star-rating

Frequently asked questions

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