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The Best Hotels for a Weekend Getaway in Winchester

If you're planning the ultimate weekend getaway in Winchester, Virginia, you'll need to find the perfect place to stay. Luckily, we've analyzed all the hotels in the area based on key criteria, so you can find the perfect place to relax and unwind for a 2-day or 3-day trip. So, our list below can help you decide where to stay for a weekend in Winchester because it has a wide variety of hotels to choose from. No matter what your budget is, you're sure to find a place that meets your needs for a long weekend escape. Whether you're traveling with family, friends, or as a couple, there are plenty of affordable and luxurious options to choose from. You can find everything from 3-star and 4-star hotels to luxury hotels, all with comfortable and relaxing rooms which are perfect for that weekend retreat you've been planning. The amenities in these hotels will vary, but you can expect to find everything you need for a comfortable stay. You'll be able to enjoy sightseeing and exploring the city with ease thanks to the great location of these hotels, too. There are also plenty of restaurants nearby where you can indulge in delicious cuisine. For those looking for more action during their weekend escape in Winchester, the area has plenty of things to do, from outdoor activities to cultural attractions. So why wait? Book your perfect 3-day trip with one of the best hotels for a weekend in Winchester below.

(Prices are listed in U.S. Dollars.)

The George Washington - A Wyndham Grand Hotel

3-star Hotel with prices starting at $149 (before taxes) - See All Prices
A Great Hotel for the Ultimate 3 Days in Winchester
  • High Quality: guest ratings are higher than average.
  • Spa
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Located at 103 East Piccadilly Street, The George Washington - A Wyndham Grand Hotel has great rooms from $149 (before taxes). It offers room service, a restaurant, a fitness center, a bar, and parking. It has a terrific 9.00 rating out of 10 from previous guests who have stayed here. Only 0 miles from the city center, visitors will especially love child care, laundry services, golf, a hot tub, and a spa and wellness center at this convenient hotel. You'll enjoy relaxing while having room service delivered.

Weekend Trip Hotel Amenities
  • Room service
  • Parking
  • Hot tub
  • Spa
  • Indoor pool
  • Airport shuttle
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Babysitting / Child Care
  • Laundry service
  • Playground
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Holiday Inn Winchester Southeast-Historic Gateway

3-star Hotel with prices starting at $126 (before taxes) - See All Prices
Perfect for 2 Days in Winchester
  • Great Value: the price is lower than average for 3-star hotels.
  • Family-Friendly
  • Heated pool
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A great place to stay is Holiday Inn Winchester Southeast-Historic Gateway which has nice rooms starting at $126. Offering room service, a restaurant, a fitness center, a bar, and hiking, it also has a great guest rating of 8.60 out of 10 from many previous guests. It's located at 333 Front Royal Pike. This fun hotel is also nice because it offers laundry services, golf, an indoor pool, free parking, and kids meals which weekend visitors will enjoy. Also, it's just 2.1 miles from the city center. You'll love relaxing in the heated pool after a busy day exploring. It's also less than the average price for weekend trip hotels, so it's a great value.

Weekend Trip Hotel Amenities
  • Room service
  • Indoor pool
  • Horse riding
  • Family-Friendly
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Laundry service
  • Free parking
  • Fishing
  • Heated pool
  • Microwave
  • Refrigerator
  • Breakfast in the room
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Hilton Garden Inn Winchester

3-star Hotel with prices starting at $147 (before taxes) - See All Prices
A Great Weekend Getaway Hotel
  • High Quality: guest ratings are higher than average.
  • Pets allowed
  • Heated pool
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We found Hilton Garden Inn Winchester to be a great place to stay, and the price starts at $147. We loved that is has room service, a restaurant, a fitness center, a bar, and laundry services, and it also has a terrific guest rating of 8.90 out of 10 from previous guests. It's located at 120 Wingate Drive. You'll also find golf, pet-friendly rooms, an indoor pool, free parking, and kids meals which weekend travelers will love. And this comfortable hotel is just 1.4 miles from the center of town. Unwinding at the restaurant after sightseeing is a nice way to end the day.

Weekend Trip Hotel Amenities
  • Room service
  • Pets allowed
  • Indoor pool
  • Golf
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Laundry service
  • Free parking
  • Heated pool
  • Coffee shop
  • Microwave
  • Refrigerator
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Hampton Inn Winchester-University/ Mall

3-star Hotel with prices starting at $142 (before taxes) - See All Prices
A Terrific Hotel for a Long Weekend in Winchester
  • Family-Friendly
  • Outdoor pool
  • Pets allowed
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With terrific rooms from $142, Hampton Inn Winchester-University/ Mall, at 1655 Apple Blossom Drive provides an outdoor pool, room service, a fitness center, breakfast, and laundry services. Its terrific guest rating is 8.70 out of 10 from previous guests staying here. Travelers will really like this relaxing hotel which also offers a free breakfast, pet-friendly rooms, free parking, laundry facilities, and air-conditioning. It's located just 1.5 miles from the city center, too. Make sure to set aside some time for swimming in the pool, too.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Family-Friendly
  • Golf
More Great Amenities
  • Fitness center
  • Laundry service
  • Free parking
  • Refrigerator
  • Saltwater pool
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TownePlace Suites Winchester

3-star Hotel with prices starting at $139 (before taxes) - See All Prices
A Great Stay for a Weekend Escape
  • Outdoor pool
  • Pets allowed
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TownePlace Suites Winchester has a great guest rating of 8.70 out of 10, and offers an outdoor pool, room service, a fitness center, breakfast, and rooms with kitchens. The great rooms here start at $139 before taxes and depending on the season. It can be found at 170 Getty Lane. Furthermore, it also offers rooms with kitchenettes, child care, laundry services, a free breakfast, and pet-friendly rooms, which is nice for visitors. Just 1.8 miles from the city center, this terrific hotel is a terrific choice. It's always nice to have a kitchenette to cook some basic meals or have an easy breakfast.

Weekend Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Breakfast included
  • Kitchen
  • Free breakfast
  • Pets allowed
  • Golf
More Great Amenities
  • Fitness center
  • Kitchenette
  • Babysitting / Child Care
  • Laundry service
  • Free parking
  • Coffee shop
  • Microwave
  • Refrigerator
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Country Inn & Suites by Radisson Winchester VA

3-star Hotel with prices starting at $127 (before taxes) - See All Prices
A Nice Option for a Weekend Retreat
  • Great Value: the price is lower than average for 3-star hotels.
  • Pets allowed
  • Heated pool
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The great guest rating of Country Inn & Suites by Radisson Winchester VA is 8.60 out of 10. This place has a fitness center, breakfast, laundry services, golf, and a free breakfast. Prices for the terrific rooms are from $127, and it's located at 141 Kernstown Commons Blvd. We also love the pet-friendly rooms, an indoor pool, free parking, laundry facilities, and family rooms which are great for weekend visitors. And since it's just 4.8 miles from the center of the town, the location is great, too. Having an indoor pool means that you can swim and have fun any time of the year. The price of this hotel is less than average for weekend trip hotels, which makes it a great value.

Weekend Trip Hotel Amenities
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Indoor pool
  • Golf
More Great Amenities
  • Fitness center
  • Laundry service
  • Free parking
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
  • Saltwater pool
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La Quinta Inn & Suites Winchester

3-star Hotel with prices starting at $110 (before taxes) - See All Prices
Perfect Hotel for a 3-day trip in Winchester
  • Great Value: the price is lower than average for 3-star hotels.
  • Family-Friendly
  • Pets allowed
  • Heated pool
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A cool place is La Quinta Inn & Suites Winchester because it has great rooms that start at $110. It has a fitness center, breakfast, laundry services, golf, and a free breakfast, it also earned a great guest rating of 8.50 out of 10 from people who have stayed here before. It's found at 1055 Milwood Pike (Rt. 50 East). Only 1.8 miles from the city center, weekend travelers will especially love pet-friendly rooms, an indoor pool, free parking, laundry facilities, and family rooms at this fun hotel. It's also less than the average price for weekend trip hotels, so it's a great value.

Weekend Trip Hotel Amenities
  • Breakfast included
  • Free breakfast
  • Pets allowed
  • Indoor pool
  • Family-Friendly
  • Golf
More Great Amenities
  • Fitness center
  • Laundry service
  • Free parking
  • Family rooms
  • Heated pool
  • Microwave
  • Refrigerator
  • Saltwater pool
View Prices and Reviews


Also, take a look at the Weekend Trip hotels in nearby destinations: Chantilly, Harrisonburg, Frederick, and Herndon.

For more terrific hotel ideas in Winchester, make sure you also see Best Pet-Friendly Hotels in Winchester, Best Hotels for First Time Visitors in Winchester, Best Hotels for One Week in Winchester, Best Hotels for One Night in Winchester, or Best Business Hotels in Winchester.


How much do hotels for a weekend visit cost in Winchester?

Winchester Average Weekend Trip Hotel Price
$134

Visitors will find a large range of terrific weekend trip hotel choices when planning a visit to Winchester, Virginia. The price of these weekend trip hotels can vary according to location, type, and amenities. The average weekend trip hotel price in Winchester, Virginia based on data from 7 hotels is an affordable $134. If you're interested in more information about hotels here, see our guide to hotel prices in Winchester.

The average prices of our suggested weekend trip hotels by star rating:

  • 3-star hotels: $134


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