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The Best Hotels for First Time Visitors in Winchester

Where to Stay on Your First Trip to Winchester

Visiting Winchester, Virginia for the first time can be an exciting, yet overwhelming experience. With so many incredible hotels to choose from, it can be difficult to know where to stay. If you're deciding where to stay for your first visit to Winchester, we've compiled a list of the best hotels for first time visitors. We analyzed all of the hotels in Winchester based on price, location, amenities, guest ratings, and more to determine which would be the ideal places to stay for first timers. Whether you're here for just a few days or longer, these hotels offer the perfect combination of amenities, location, and price. For those visiting Winchester for the first time, it's important to choose a hotel in a safe and convenient area to make the most of your first visit. You'll want to be close to the activities, shopping, and dining options, of course. When looking for hotels, consider the amenities they offer. Some hotels may have a fitness center, a bar or restaurant, a pool, or even a spa. All of these features can add to your overall enjoyment if you've never been to Winchester before. Also, guest ratings and reviews are also important to consider when choosing a hotel. Whether you're visiting Winchester for the first time, or you're a seasoned traveler, the best hotels in Winchester for first-timers offer the perfect combination of comfort, convenience, and affordability. So, here's our list of suggestions for your next trip.

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

The George Washington - A Wyndham Grand Hotel

3-star Hotel with prices starting at $133 (before taxes) - See All Prices
A Good Stay for Your First Trip
  • High Quality: guest ratings are higher than average.
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Located at 103 East Piccadilly Street, The George Washington - A Wyndham Grand Hotel has great rooms from $133 (before taxes). It offers room service, room service, a restaurant, a restaurant, and a fitness center. It has a terrific 9.10 rating out of 10 from previous guests who have stayed here. Only 0 miles from the city center, first time visitors will especially love a fitness center, a bar, a bar, parking, and parking at this relaxing hotel. You'll enjoy relaxing while having room service delivered.

First Time Trip Hotel Amenities
  • Room service
  • Room service
  • Parking
  • Parking
  • Spa
  • Spa
  • Indoor pool
  • Indoor pool
  • Airport shuttle
  • Airport shuttle
More Great Amenities
  • Restaurant
  • Restaurant
  • Fitness center
  • Fitness center
  • Bar/Lounge
  • Bar/Lounge
  • Babysitting / Child Care
  • Babysitting / Child Care
  • Laundry service
  • Laundry service
  • Hot tub
  • Hot tub
  • Family rooms
  • Family rooms
  • Playground
  • Playground
  • Saltwater pool
  • Saltwater pool
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Courtyard by Marriott Winchester Medical Center

3-star Hotel with prices starting at $112 (before taxes) - See All Prices
Perfect for Your First Time in Winchester
  • Great Value: the price is lower than average for 3-star hotels.
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A great place to stay is Courtyard by Marriott Winchester Medical Center which has nice rooms starting at $112. Offering a restaurant, a fitness center, a bar, laundry services, and a hot tub, it also has a great guest rating of 8.40 out of 10 from many previous guests. It's located at 300 Marriott Drive. This convenient hotel is also nice because it offers an indoor pool, free parking, laundry facilities, bicycle rental, and air-conditioning which visitors will enjoy. Also, it's just 2 miles from the city center. The restaurant serves delicious food, too.

First Time Trip Hotel Amenities
  • Indoor pool
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Laundry service
  • Hot tub
  • Free parking
  • Bicycle rental
  • Microwave
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Hampton Inn Winchester N/Conference Center

3-star Hotel with prices starting at $124 (before taxes) - See All Prices
Perfect for First-Timers
  • High Quality: guest ratings are higher than average.
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We found Hampton Inn Winchester N/Conference Center to be a great place to stay, and the price starts at $124. We loved that is has an outdoor pool, skiing, a fitness center, hiking, and laundry services, and it also has a terrific guest rating of 9.20 out of 10 from previous guests. It's located at 1204 Berryville Avenue. You'll also find golf, free parking, horse riding, laundry facilities, and family rooms which travelers will love. And this fun hotel is just 1.2 miles from the center of town. The pool here was very nice, relaxing, and fun.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Skiing
  • Horse riding
More Great Amenities
  • Fitness center
  • Hiking
  • Laundry service
  • Free parking
  • Family rooms
  • Microwave
  • Refrigerator
View Prices and Reviews


TownePlace Suites by Marriott Winchester

3-star Hotel with prices starting at $122 (before taxes) - See All Prices
Among the Best Places to Stay for a First Visit to Winchester
  • High Quality: guest ratings are higher than average.
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With terrific rooms from $122, TownePlace Suites by Marriott Winchester, at 170 Getty Lane provides an outdoor pool, room service, a fitness center, rooms with kitchens, and rooms with kitchenettes. Its terrific guest rating is 9.20 out of 10 from previous guests staying here. New visitors will really like this amazing hotel which also offers child care, laundry services, a free breakfast, pet-friendly rooms, and free parking. It's located just 1.7 miles from the city center, too. We always love being able to prepare simple meals in a hotel room, and the kitchenette here was teriffic.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Kitchen
  • Free breakfast
More Great Amenities
  • Fitness center
  • Kitchenette
  • Babysitting / Child Care
  • Laundry service
  • Pets allowed
  • Free parking
  • Bicycle rental
  • Microwave
  • Refrigerator
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Holiday Inn Winchester Se-Historic Gateway By IHG

3-star Hotel with prices starting at $86 (before taxes) - See All Prices
Perfect Hotel to Make the Most of Your First Visit
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Family-Friendly
  • Heated pool
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Holiday Inn Winchester Se-Historic Gateway By IHG has a great guest rating of 8.90 out of 10, and offers room service, a restaurant, a fitness center, a bar, and hiking. The great rooms here start at $86 before taxes and depending on the season. It can be found at 333 Front Royal Pike. Furthermore, it also offers laundry services, golf, pet-friendly rooms, an indoor pool, and free parking, which is nice for first time visitors. Just 2.1 miles from the city center, this fantastic hotel is a terrific choice. It's always nice having a heated pool to relax in. We found the price of this hotel to be a great value because the price is less than average for first time trip hotels.

First Time Trip Hotel Amenities
  • Room service
  • Indoor pool
  • Horse riding
  • Family-Friendly
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Hiking
  • Laundry service
  • Pets allowed
  • Free parking
  • Heated pool
  • Microwave
  • Refrigerator
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Hilton Garden Inn Winchester

3-star Hotel with prices starting at $131 (before taxes) - See All Prices
Great Hotel for First Time Visitors
  • Heated pool
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The great guest rating of Hilton Garden Inn Winchester is 8.60 out of 10. This place has room service, a restaurant, a fitness center, a bar, and laundry services. Prices for the terrific rooms are from $131, and it's located at 120 Wingate Drive. We also love the golf, pet-friendly rooms, an indoor pool, free parking, and laundry facilities which are great for visitors. And since it's just 1.4 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.

First Time Trip Hotel Amenities
  • Room service
  • Indoor pool
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Laundry service
  • Pets allowed
  • Free parking
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


Quality Inn Winchester

Inn with prices starting at $82 (before taxes) - See All Prices
Perfect for Your First Visit to Winchester
  • Great Value: the price is lower than average for 2-star hotels.
  • High Quality: guest ratings are higher than average.
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A cool place is Quality Inn Winchester because it has great rooms that start at $82. It has a restaurant, a fitness center, laundry services, pet-friendly rooms, and free parking, it also earned a great guest rating of 8.90 out of 10 from people who have stayed here before. It's found at 1601 Martinsburg Pike. Only 2.5 miles from the city center, travelers will especially love laundry facilities, air-conditioning, a 24-hour desk, a microwave, and a refrigerator at this convenient hotel. It's also less than the average price for first time trip hotels, so it's a great value.

First Time Trip Hotel Amenities
More Great Amenities
  • Restaurant
  • Fitness center
  • Laundry service
  • Pets allowed
  • Free parking
  • Microwave
  • Refrigerator
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Hampton Inn Winchester-University/Mall Area

3-star Hotel with prices starting at $111 (before taxes) - See All Prices
A Good Stay for Your First Trip
  • Great Value: the price is lower than average for 3-star hotels.
  • Family-Friendly
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Hampton Inn Winchester-University/Mall Area offers an outdoor pool, room service, a fitness center, laundry services, and pet-friendly rooms which we really like. The terrific rooms here start at $111 (before taxes). It's located at 640 East Jubal Early Drive and has earned a guest rating of 8.80/10. This fun hotel is also nice because it offers free parking, laundry facilities, air-conditioning, a 24-hour desk, and a refrigerator which new visitors will enjoy. Also, it's just 1.4 miles from the city center.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Family-Friendly
More Great Amenities
  • Fitness center
  • Laundry service
  • Pets allowed
  • Free parking
  • Refrigerator
  • Saltwater pool
View Prices and Reviews


Fairfield Inn & Suites by Marriott Winchester

2-star Hotel with prices starting at $101 (before taxes) - See All Prices
Perfect for Your First Time in Winchester
  • Great Value: the price is lower than average for 2-star hotels.
  • Heated pool
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Located at 250 Front Royal Pike, Fairfield Inn & Suites by Marriott Winchester has great rooms from $101 (before taxes). It offers a fitness center, laundry services, a free breakfast, a hot tub, and an indoor pool. It has a terrific 8.80 rating out of 10 from previous guests who have stayed here. You'll also find free parking, laundry facilities, bicycle rental, a heated pool, and air-conditioning which first time visitors will love. And this amazing hotel is just 1.9 miles from the center of town. Everyone loves a good hot tub, and this one is really nice. It's a great value, as the price is less than the average for first time trip hotels.

First Time Trip Hotel Amenities
  • Free breakfast
  • Indoor pool
More Great Amenities
  • Fitness center
  • Laundry service
  • Hot tub
  • Free parking
  • Bicycle rental
  • Heated pool
  • Microwave
  • Refrigerator
View Prices and Reviews


SpringHill Suites by Marriott Winchester

2-star Hotel with prices starting at $123 (before taxes) - See All Prices
Perfect for First-Timers
  • High Quality: guest ratings are higher than average.
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A great place to stay is SpringHill Suites by Marriott Winchester which has nice rooms starting at $123. Offering a fitness center, laundry services, a free breakfast, an indoor pool, and free parking, it also has a great guest rating of 9.20 out of 10 from many previous guests. It's located at 280 Market Street. Visitors will really like this fantastic hotel which also offers air-conditioning, a 24-hour desk, a microwave, a refrigerator, and a pet-free facility. It's located just 3.1 miles from the city center, too.

First Time Trip Hotel Amenities
  • Free breakfast
  • Indoor pool
More Great Amenities
  • Fitness center
  • Laundry service
  • Free parking
  • Microwave
  • Refrigerator
View Prices and Reviews


Also, take a look at the first time trip hotels in nearby destinations: Winchester, Gettysburg, Harrisonburg, Gaithersburg, 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 a Weekend Getaway 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 first-time visitors cost in Winchester?

Winchester Average First Time Trip Hotel Price
$109

Visitors will find a large range of terrific first time trip hotel choices when planning a visit to Winchester, Virginia. The price of these first time trip hotels can vary according to location, type, and amenities. The average first time trip hotel price in Winchester, Virginia based on data from 14 hotels is an affordable $109. If you're interested in more information about hotels here, see our guide to hotel prices in Winchester.

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

  • 3-star hotels: $113
  • 2-star hotels: $102


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