Winchester Hotels from S$95

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Check Winchester hotel prices

Tomorrow night
This weekend

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top 10 trending Winchester hotels

La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1312)
"Everything we needed traveling all day."
The price is S$168
per night
12 May - 13 May
La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 star property
8.0 out of 10, Very good, (1059)
"Reliable accommodation"
The price is S$98
per night
19 May - 20 May
Travelodge by Wyndham Winchester
Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
8.2 out of 10, Very good, (902)
"The hotel was a little rundown, but the staff was amazing and the food was great. Overall, our stay was wonderful. Thank you."
The price is S$97
per night
9 Jun - 10 Jun
Days Inn by Wyndham Charles Town/Harpers Ferry
Save an average of 15% on thousands of hotels when you're signed in
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (748)
"Good place to stay "
The price is S$124
per night
2 Jun - 3 Jun
Microtel Inn & Suites by Wyndham Winchester
The Inn at Charles Town
3.0 star property
8.4 out of 10, Very good, (326)
"I appreciate having a complimentary breakfast to start the day. My only complaint is that I sprung for the trackside room (more expensive) and there was not an ottoman for my legs. The standard room has one."
The price is S$168
per night
13 May - 14 May
The Inn at Charles Town
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1007)
"We loved The George Washington Hotel! It has an excellent location for restaurants and the walking mall. It’s easy to drive to places, and the facilities were beautiful! We had a wonderful time. We loved the pool and ordering room service. We hope the spa gets up and running soon; it’s closed for now. "
The price is S$192
per night
27 May - 28 May
The George Washington Hotel, A Wyndham Grand Hotel
Sleep Inn & Suites
2.5 star property
8.2 out of 10, Very good, (1000)
"Great place for a quick overnight stop. Clean, comfortable rooms and they have a small indoor pool. Breakfast leaves a little to be desired, but there's a buffet right next door and IHOP around the corner. We usually choose to stay here when we visit Winchester."
The price is S$111
per night
12 May - 13 May
Sleep Inn & Suites
Comfort Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (917)
"Safe Clean Close to major exits"
The price is S$139
per night
12 May - 13 May
Comfort Inn & Suites
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (1001)
"This hotel is great! "
The price is S$150
per night
19 May - 20 May
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
Red Roof Inn Winchester, VA
2.0 star property
7.4 out of 10, Good, (1004)
"Easy parking, plenty of places to eat! LVP flooring: feels so clean to walk on, AC worked great, bed comfortable...Fresh coffee & yougurt in the AM this is our go to stopover when we go south! "
The price is S$106
per night
12 May - 13 May
Red Roof Inn Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1002)
"The location was close to several eating establishments all within a 5 minute walk. The staff was very friendly and eager to help. The room was a little dated but very comfy. The highway was close but you could not hear the vehicle noise. The room was well worth the price."
The price is S$136
per night
27 May - 28 May
Country Inn & Suites by Radisson, Winchester, VA
Home2 Suites by Hilton Charles Town
3.0 star property
9.8 out of 10, Exceptional, (613)
"The staff were all super-friendly. Our room was fantastic. the whole stay was exactly what we needed. we will be back!!!!"
The price is S$231
per night
26 May - 27 May
Home2 Suites by Hilton Charles Town
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Check in- The young man who checked me in was marvelous. Unfortunately, I didnt get his name. He checked me early with no problem. The afternoon staff were also excellent. They helped me finding the route of the Apple Blosoom parade. The lobby area is ckean and well maintained."
The price is S$159
per night
2 Jun - 3 Jun
Spark by Hilton Winchester
Rodeway Inn & Suites - Charles Town, WV
2.0 star property
8.8 out of 10, Excellent, (789)
"the friendliness and location "
The price is S$110
per night
12 May - 13 May
Rodeway Inn & Suites - Charles Town, WV
Quality Inn
2.5 star property
8.8 out of 10, Excellent, (990)
"Highly recommend. Clean comfortable and friendly staff. Location is convenient to major highway etc congested spot for a hotel but certainly did not effect our wknd stay. Thank you!"
The price is S$124
per night
27 May - 28 May
Quality Inn
Hilton Garden Inn Martinsburg
3.0 star property
9.2 out of 10, Wonderful, (517)
"Always a nice place to stay. Close and convenient to shopping and restaurants, yet quiet. Wish the pillows were a bit firmer. Otherwise, great place and will definitely be back when in Martinsburg again!"
The price is S$184
per night
12 May - 13 May
Hilton Garden Inn Martinsburg
Hampton Inn & Suites Charles Town
2.5 star property
9.4 out of 10, Exceptional, (1001)
"The staff was amazing and was very clean "
The price is S$205
per night
26 May - 27 May
Hampton Inn & Suites Charles Town
Fairfield Inn & Suites by Marriott Winchester
2.5 star property
8.8 out of 10, Excellent, (584)
"We stayed for one night and it was perfect!"
The price is S$174
per night
26 May - 27 May
Fairfield Inn & Suites by Marriott Winchester
Motel 6 Charles Town, WV
2.0 star property
7.6 out of 10, Good, (621)
"Easy to find. Clean rooms"
The price is S$95
per night
13 May - 14 May
Motel 6 Charles Town, WV
Motel 6 Winchester, VA
2.0 star property
8.0 out of 10, Very good, (1002)
"Great service"
The price is S$107
per night
13 May - 14 May
Motel 6 Winchester, VA
Don't see what you're looking for?
See all available properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What's the best hotel for a couple visiting Winchester?

The George Washington Hotel, A Wyndham Grand Hotel is a favourite hotel for couples, and features a full-service spa and 2 restaurants. Other good choices for a stay with your sweetheart include SpringHill Suites by Marriott Winchester and Hilton Garden Inn Winchester. See all romantic hotels in Winchester.

What's the best luxury hotel in Winchester?

Celebration Retreat is a 5-star holiday home with spa services and in-room kitchens, and it's a popular choice for Expedia travellers looking for an elegant place to stay.

What's the best boutique-style hotel in Winchester?

The George Washington Hotel, A Wyndham Grand Hotel is a favourite 3.5-star hotel with our travellers looking for stylish accommodation, and features 90 guestrooms, 2 restaurants and a bar. If you'd prefer to stay at a boutique hotel, also consider La Quinta Inn & Suites by Wyndham Winchester.

What's the best hotel for a golf holiday in Winchester?

La Quinta Inn & Suites by Wyndham Winchester is a hotel featuring free breakfast and free WiFi, and it's a top choice for golfing nearby. Other good options to stay near a golf course include Fairfield Inn & Suites by Marriott Winchester and Quality Inn. You can tee off at Rock Harbor Golf Course during your trip. See more golf hotels in Winchester.

What's the best accommodation in Winchester to learn about local history?

Based on our travel expertise, La Quinta Inn & Suites by Wyndham Winchester is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Other choices close to historic sites include Spark by Hilton Winchester and Fairfield Inn & Suites by Marriott Winchester. Also, notable landmarks to visit include Stonewall Jackson's Headquarters, Patsy Cline Historic House and The Kernstown Battlefield.

How is it to stay in Winchester?

Families will find child-friendly activities in Winchester, and visitors give high marks for the shopping and top-notch restaurants. Scenic and urban, this city attracts tourists with its theatres and entertainment. In Winchester, there are 56 hotels and other accommodation options to choose from. Find out more about Winchester.

What is there to see in Winchester?

Cultural venues include Museum of the Shenandoah Valley, Bright Box Theater and Winchester Little Theater. Families come for attractions such as Shenandoah Valley Discovery Museum, Nalls Farm Market and Rocking S Ranch. Notable for its historic sites, landmarks like Stonewall Jackson's Headquarters, Patsy Cline Historic House and The Kernstown Battlefield are not to be missed. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.