Winchester Hotels from S$80

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great stay for a great price!"
The price is S$135
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Winchester, VA

Courtyard by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (842)
"Great location, great amenities "
The price is S$141
includes taxes & fees
27 Jul - 28 Jul
Courtyard by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
9.0 out of 10, Wonderful, (738)
"Clean and comfortable room, wonderful breakfast, pleasant personnel"
The price is S$135
includes taxes & fees
20 Jul - 21 Jul
Fairfield Inn & Suites by Marriott Winchester

Comfort Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1002)
"Would stay again. "
The price is S$136
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn & Suites

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.2 out of 10, Very good, (1005)
"Great location off the highway, restaurant on site was very good, staff was friendly and quick check in"
The price is S$102
includes taxes & fees
27 Jul - 28 Jul
Ramada by Wyndham Strasburg/Shenandoah Valley

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Great stay!"
The price is S$157
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn Front Royal

SpringHill Suites by Marriott Winchester

2.5 star property
9.4 out of 10, Exceptional, (659)
The price is S$156
includes taxes & fees
27 Jul - 28 Jul
SpringHill Suites by Marriott Winchester

Quality Inn

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great place , great front desk staff, super clean & very quiet"
The price is S$129
includes taxes & fees
24 Jul - 25 Jul
Quality Inn

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (757)
"Always great!"
The price is S$123
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Winchester South-Stephens City by IHG

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (2079)
"We only stayed one night as we were passing through but it was an excellent place to stay. "
The price is S$162
includes taxes & fees
20 Jul - 21 Jul
La Quinta Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.0 out of 10, Wonderful, (1305)
"Clean comfortable room, friendly staff. "
The price is S$118
includes taxes & fees
27 Jul - 28 Jul
Microtel Inn & Suites by Wyndham Winchester

Spark by Hilton Winchester

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Clean, comfortable, quiet, safe, but complimentary breakfast was lackluster."
The price is S$132
includes taxes & fees
17 Aug - 18 Aug
Spark by Hilton Winchester

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (763)
"Very friendly staff and clean property"
The price is S$169
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Winchester by IHG

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (782)
"Well kept, clean, good breakfast."
The price is S$172
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn Winchester N/Conference Center, VA

TRU By Hilton Winchester

2.5 star property
9.0 out of 10, Wonderful, (681)
"I stop every time I travel south and it is consistently a great hotel and staff is phenomenal"
The price is S$136
includes taxes & fees
13 Aug - 14 Aug
TRU By Hilton Winchester

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Great hotel"
The price is S$144
includes taxes & fees
27 Jul - 28 Jul
Fairfield Inn & Suites Strasburg Shenandoah Valley

Travelodge by Wyndham Winchester

2.5 star property
8.4 out of 10, Very good, (1110)
"The stay was great for the price."
The price is S$96
includes taxes & fees
20 Jul - 21 Jul
Travelodge by Wyndham Winchester

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1009)
"Convenient to Skyline Drive in Shenandoah National Park."
The price is S$106
includes taxes & fees
20 Jul - 21 Jul
Super 8 by Wyndham Front Royal

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Staff was super nice when checking in!"
The price is S$134
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Winchester Se-Historic Gateway by IHG

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Great stay, great location. "
The price is S$175
includes taxes & fees
27 Jul - 28 Jul
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most.
Old Town Winchester map

Old Town Winchester

2 out of top 10 points of interest in this area

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Winchester Historic District map

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Winchester and related destinations

Come to Winchester and enjoy its history, dining and entertainment.

Top Winchester Hotel Reviews

Frequently asked questions

Where is the best place to stay in Winchester?

Comfort Inn & Suites is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Other top choices based on reviews include SpringHill Suites by Marriott Winchester and The George Washington Hotel, A Wyndham Grand Hotel. See all available top hotels, or vacation rentals in Winchester.

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 budget-friendly accommodation in Winchester?

Based on reviews, La Quinta Inn & Suites by Wyndham Winchester is a popular hotel for our travellers who want a more economical choice, and features free buffet breakfast and free Wi-Fi. Other options to stay on the cheap include Travelodge by Wyndham Winchester and Microtel Inn & Suites by Wyndham Winchester. View all budget hotels in Winchester.

What's the best family accommodation in Winchester?

Holiday Inn Winchester Se-Historic Gateway by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your child-friendly holiday include Country Inn & Suites by Radisson, Winchester, VA and Quality Inn. Also, attractions such as Shenandoah Valley Discovery Museum and Nalls Farm Market are fun for children of all ages. Find more child-friendly accommodations in Winchester.

What's the best LGBTQ-friendly place to stay in Winchester?

La Quinta Inn & Suites by Wyndham Winchester is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. Holiday Inn Winchester Se-Historic Gateway by IHG and Fairfield Inn & Suites by Marriott Winchester are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.

What's the best dog-friendly accommodation option in Winchester?

La Quinta Inn & Suites by Wyndham Winchester is a top hotel for people travelling with their pets, and offers an indoor pool and free WiFi for its human guests. Other good choices for you and your pet include Comfort Inn & Suites and Country Inn & Suites by Radisson, Winchester, VA. See more pet-friendly hotel accommodations 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 are some hotels with pools in Winchester?

La Quinta Inn & Suites by Wyndham Winchester is a top hotel with an indoor pool, free buffet breakfast and free WiFi. Other choices that offer an on-site pool include TownePlace Suites by Marriott Winchester and Microtel Inn & Suites by Wyndham Winchester. View all hotels with pools in Winchester.

What is the best spa hotel in Winchester?

The George Washington Hotel, A Wyndham Grand Hotel is a top spa hotel featuring a 24-hour fitness centre, a bar and an indoor pool. Spend an afternoon at the spa where you’ll find massage treatments. In-room massages are also available. See all spa hotels in Winchester.

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 73 hotels and other accommodation options to choose from. Find out more about Winchester.

What is there to see in Winchester?

Cultural venues include Bright Box Theater, Winchester Little Theater and Museum of the Shenandoah Valley. Families come for attractions such as Shenandoah Valley Discovery Museum, Nalls Farm Market and Rocking S Ranch. Notable for its historic sites, landmarks like Patsy Cline Historic House, Mt Hebron Cemetery and Stonewall Jackson's Headquarters 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.