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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 $149 (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 $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, first time visitors will especially love child care, laundry services, golf, a hot tub, and a spa and wellness center at this relaxing hotel. You'll enjoy relaxing while having room service delivered.

First Time Trip Hotel Amenities
  • Room service
  • Parking
  • Spa
  • Indoor pool
  • Airport shuttle
More Great Amenities
  • Restaurant
  • Fitness center
  • Bar/Lounge
  • Babysitting / Child Care
  • Laundry service
  • Hot tub
  • Playground
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Hilton Garden Inn Winchester

3-star Hotel with prices starting at $147 (before taxes) - See All Prices
Perfect for Your First Time in Winchester
  • High Quality: guest ratings are higher than average.
  • Heated pool
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A great place to stay is Hilton Garden Inn Winchester which has nice rooms starting at $147. Offering room service, a restaurant, a fitness center, a bar, and laundry services, it also has a great guest rating of 8.90 out of 10 from many previous guests. It's located at 120 Wingate Drive. This convenient hotel is also nice because it offers golf, pet-friendly rooms, an indoor pool, free parking, and kids meals which visitors will enjoy. Also, it's just 1.4 miles from the city center. You'll love relaxing in the heated pool after a busy day exploring.

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
  • Coffee shop
  • Microwave
  • Refrigerator
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Hampton Inn Winchester

2-star Hotel with prices starting at $151 (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 to be a great place to stay, and the price starts at $151. We loved that is has an outdoor pool, skiing, a fitness center, breakfast, and hiking, and it also has a terrific guest rating of 8.70 out of 10 from previous guests. It's located at 1204 Berryville Avenue. You'll also find laundry services, golf, a free breakfast, pet-friendly rooms, and free parking 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
  • Breakfast included
  • Free breakfast
  • Horse riding
More Great Amenities
  • Fitness center
  • Hiking
  • Laundry service
  • Pets allowed
  • Free parking
  • Fishing
  • Family rooms
  • Microwave
  • Refrigerator
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Holiday Inn Winchester Southeast-Historic Gateway

3-star Hotel with prices starting at $126 (before taxes) - See All Prices
Among the Best Places to Stay for a First Visit to Winchester
  • 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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With terrific rooms from $126, Holiday Inn Winchester Southeast-Historic Gateway, at 333 Front Royal Pike provides room service, a restaurant, a fitness center, a bar, and hiking. Its terrific guest rating is 8.60 out of 10 from previous guests staying here. New visitors will really like this amazing hotel which also offers laundry services, golf, an indoor pool, free parking, and kids meals. It's located just 2.1 miles from the city center, too. The service at the restaurant is terrific, and so is the food. It's a great value, as the price is less than the 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
  • Free parking
  • Fishing
  • Heated pool
  • Microwave
  • Refrigerator
  • Breakfast in the room
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Hampton Inn Winchester-University/ Mall

3-star Hotel with prices starting at $142 (before taxes) - See All Prices
Perfect Hotel to Make the Most of Your First Visit
  • High Quality: guest ratings are higher than average.
  • Family-Friendly
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Hampton Inn Winchester-University/ Mall has a great guest rating of 8.70 out of 10, and offers an outdoor pool, room service, a fitness center, breakfast, and laundry services. The great rooms here start at $142 before taxes and depending on the season. It can be found at 1655 Apple Blossom Drive. Furthermore, it also offers a free breakfast, pet-friendly rooms, free parking, laundry facilities, and air-conditioning, which is nice for first time visitors. Just 1.5 miles from the city center, this fantastic hotel is a terrific choice.

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


TownePlace Suites Winchester

3-star Hotel with prices starting at $139 (before taxes) - See All Prices
Great Hotel for First Time Visitors
  • High Quality: guest ratings are higher than average.
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The great guest rating of TownePlace Suites Winchester is 8.70 out of 10. This place has an outdoor pool, room service, a fitness center, breakfast, and rooms with kitchens. Prices for the terrific rooms are from $139, and it's located at 170 Getty Lane. We also love the rooms with kitchenettes, child care, laundry services, a free breakfast, and pet-friendly rooms which are great for visitors. And since it's just 1.8 miles from the center of the town, the location is great, too. Being able to prepare food in the room is also very convenient.

First Time Trip Hotel Amenities
  • Outdoor pool
  • Room service
  • Breakfast included
  • Kitchen
  • Free breakfast
More Great Amenities
  • Fitness center
  • Kitchenette
  • Babysitting / Child Care
  • Laundry service
  • Pets allowed
  • Free parking
  • Coffee shop
  • Microwave
  • Refrigerator
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Quality Inn Winchester

2-star Hotel with prices starting at $118 (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.
  • Pool
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A cool place is Quality Inn Winchester because it has great rooms that start at $118. It has a pool, a restaurant, a fitness center, breakfast, and laundry services, it also earned a great guest rating of 8.60 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 a free breakfast, pet-friendly rooms, free parking, laundry facilities, and air-conditioning 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
  • Pool
  • Breakfast included
  • Free breakfast
More Great Amenities
  • Restaurant
  • Fitness center
  • Laundry service
  • Pets allowed
  • Free parking
  • Microwave
  • Refrigerator
View Prices and Reviews


Sleep Inn & Suites Winchester

2-star Hotel with prices starting at $83 (before taxes) - See All Prices
A Good Stay for Your First Trip
  • Great Value: the price is lower than average for 2-star hotels.
  • Heated pool
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Sleep Inn & Suites Winchester offers a fitness center, laundry services, a free breakfast, city views, and an indoor pool which we really like. The terrific rooms here start at $83 (before taxes). It's located at 140 Costello Dr. And has earned a guest rating of 8.00/10. This fun hotel is also nice because it offers free parking, laundry facilities, a heated pool, air-conditioning, and a 24-hour desk which new visitors will enjoy. Also, it's just 2 miles from the city center. Everyone loves a nice indoor pool, and the one here does not disappoint! It's a great value, too, because it's less than the average price for first time trip hotels.

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


Country Inn & Suites by Radisson Winchester VA

3-star Hotel with prices starting at $127 (before taxes) - See All Prices
Perfect for Your First Time in Winchester
  • Great Value: the price is lower than average for 3-star hotels.
  • High Quality: guest ratings are higher than average.
  • Heated pool
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Located at 141 Kernstown Commons Blvd, Country Inn & Suites by Radisson Winchester VA has great rooms from $127 (before taxes). It offers a fitness center, breakfast, laundry services, golf, and a free breakfast. It has a terrific 8.60 rating out of 10 from previous guests who have stayed here. You'll also find pet-friendly rooms, an indoor pool, free parking, laundry facilities, and family rooms which first time visitors will love. And this amazing hotel is just 4.8 miles from the center of town. It's a great value, as the price is less than the average for first time trip hotels.

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


Holiday Inn Express and Suites Winchester

2-star Hotel with prices starting at $151 (before taxes) - See All Prices
Perfect for First-Timers
  • High Quality: guest ratings are higher than average.
  • Heated pool
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A great place to stay is Holiday Inn Express and Suites Winchester which has nice rooms starting at $151. Offering a fitness center, laundry services, a free breakfast, a hot tub, and an indoor pool, it also has a great guest rating of 8.60 out of 10 from many previous guests. It's located at 142 Fox Ridge Lane. Visitors will really like this fantastic hotel which also offers free parking, laundry facilities, a heated pool, air-conditioning, and a 24-hour desk. It's located just 1.8 miles from the city center, too. You'll love relaxing in the hot tub at the end of the day, too.

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


Also, take a look at the First Time Trip hotels in nearby destinations: Frederick, Harrisonburg, Hagerstown, and Chantilly.

For more terrific hotel ideas in Winchester, make sure you also see Best Pet-Friendly Hotels 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
$130

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 13 hotels is an affordable $130. 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: $134
  • 2-star hotels: $126


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