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

Go beyond your typical stay in Winchester

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Our top choices for Winchester hotels

A swimming pool with a water slide and a lifeguard stand.

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.

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

1. Dutch Wonderland Inn

Dutch Countryside

Lorraine

$100 nightly

$111 total

Oct 11 - Oct 12

Total with taxes and fees

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

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.

A hotel room with a large bed, a red armchair, a small desk, a bathroom with a bathtub, and a TV.

2. Parkview Inn & Suites Lancaster

Dutch Countryside

John

$97 nightly

$108 total

Oct 25 - Oct 26

Total with taxes and fees

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 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

Newark

Sam

$110 nightly

$122 total

Oct 25 - Oct 26

Total with taxes and fees

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

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."

A spacious lobby with a large stone fireplace, modern seating, and large windows with forest views.

4. Great Wolf Lodge Perryville

Perryville

Beriuska

$207 nightly

$232 total

Oct 12 - Oct 13

Total with taxes and fees

A lobby with seating, a reception desk, and a cityscape mural on the wall.

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

A hotel room with a bed, a sofa, a small table, a TV, and a framed picture 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.

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

Elkton

Simon

$106 nightly

$119 total

Oct 25 - Oct 26

Total with taxes and fees

A hotel lobby with a reception desk, a blue sofa, a staircase, and a wooden floor.

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.

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

Brian

$80 nightly

$89 total

Oct 11 - Oct 12

Total with taxes and fees

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 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.

7. La Quinta Inn & Suites by Wyndham Lancaster

Dutch Countryside

Judy

$91 nightly

$101 total

Nov 1 - Nov 2

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 hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.

8. Hampton Inn Elkton

Elkton

Cathy

$102 nightly

$114 total

Oct 19 - Oct 20

Total with taxes and fees

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

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 bedroom with a bed, a desk, two chairs, a round table, and a window with blinds.

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

9. Red Caboose Motel

Ronks

Stacy

$110 nightly

$122 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 hotel room with a large bed, a nightstand with a lamp, a floral armchair, and a window with curtains.

A pool area with lounge chairs and tables, surrounded by large windows and potted plants.

10. Fulton Steamboat Inn

Dutch Countryside

Annmarie

$167 nightly

$186 total

Oct 13 - Oct 14

Total with taxes and fees

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

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.

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

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

Elkton

Heather

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

12. Hyatt Place Newark - Main Street

Newark

Kirsten

$182 nightly

$202 total

Nov 3 - Nov 4

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 1 - Nov 2

Total with taxes and fees

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

A gym with cardio machines, weightlifting equipment, and a wall-mounted TV.

14. DoubleTree by Hilton Hotel Wilmington

Wilmington

Lisa

$118 nightly

$131 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 motel with a parking lot, a landscaped area with flowers, and a sign reading 'ELKTON LODGE.'

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

A view from a balcony with a metal railing, a parking lot, and a building with a McDonald's sign in the background.

15. Elkton Lodge - Newark - Elkton - University Gateway

Elkton

Joseph

$100 nightly

$112 total

Oct 11 - Oct 12

Total with taxes and fees

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

Jean

$116 nightly

$129 total

Oct 18 - Oct 19

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 reception area with a modern desk, a chair, a potted plant, and a large abstract artwork on the wall.

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 15 - Oct 16

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

WILSON

$109 nightly

$121 total

Nov 3 - Nov 4

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 view from a window with a wooden deck and greenery outside.

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

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

19. Elk Forge B&B Inn & Day Spa

Elkton

Sarah

$116 nightly

$123 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 modern living room with a fireplace, sofas, armchairs, and a flat-screen TV.

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

A display of snack and microwave products in a store.

20. Sonesta Select Newark Christiana Mall

Newark

Lisa

$127 nightly

$141 total

Oct 9 - Oct 10

Total with taxes and fees

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Top Winchester Hotel Reviews

Red Roof Inn & Suites Newark - University

8/10 Good

"Room was very clean and provided extra towels"

Ramada by Wyndham Newark/Wilmington

8/10 Good

"The hotel could use some sprucing up. It looks old and tired."

Red Roof Inn & Suites Wilmington - New Castle

10/10 Excellent

"It's an older but well maintained property. The lobby was inviting and my room clean. The only draw back was the long walk down the hall but there is another entrance at the other end of the building. My daughter loved the ice cream vending machine."

Extended Stay America Suites Newark Christiana Wilmington

10/10 Excellent

"I was happy with the stay which is why I continue to chose that hotel over others."

Embassy Suites by Hilton Newark Wilmington South

8/10 Good

"We had one roll of TP 😂and asked house keeping staff to replenish but they didn’t come back. Nevertheless, the front desk was very helpful and resupplied!"

Sheraton Suites Wilmington Downtown

10/10 Excellent

"Clean and quiet.. everything was great!"

Comfort Inn & Suites Newark - Wilmington

8/10 Good

"i did not like the constant smell of marijuana throughout the building.. even going outside, staff could be seen on breaks smoking marijuanap"

More cheap stays in Winchester

Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE

$60 nightly

$66 total

Nov 1 - Nov 2

Total with taxes and fees

Red Roof Inn & Suites Newark - University

1119 S College Avenue Newark DE

$69 nightly

$77 total

Nov 1 - Nov 2

Total with taxes and fees

5.6/10 (1,005 reviews)

Red Roof Inn Perryville

61 Heather Lane Perryville MD

$70 nightly

$79 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (244 reviews)

Baymont by Wyndham Newark at University of Delaware

630 S College Ave Newark DE

$80 nightly

$89 total

Oct 11 - Oct 12

Total with taxes and fees

Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE

$94 nightly

$103 total

Nov 1 - Nov 2

Total with taxes and fees

Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE

$115 nightly

$115 total

Oct 18 - Oct 19

Total with taxes and fees

8/10 Very Good! (480 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

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

Red Roof Inn & Suites Newark - University

Ramada by Wyndham Newark/Wilmington

Red Roof Inn & Suites Wilmington - New Castle

Extended Stay America Suites Newark Christiana Wilmington

Embassy Suites by Hilton Newark Wilmington South

Sheraton Suites Wilmington Downtown

Comfort Inn & Suites Newark - Wilmington

More cheap stays in Winchester

Quality Inn Newark - Wilmington

Red Roof Inn & Suites Newark - University

Red Roof Inn Perryville

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

Explore a world of travel with Expedia