Known for its rich history and picturesque landscapes, Winchester offers a unique blend of small-town charm and big-city amenities. The city was established in 1744 and is home to Alesatian Brewing Company, an award-winning brewery where tourists enjoy craft beer and pizza. For those who want to engage in bike riding, trekking, or bird watching, Abrams Creek Wetlands Preserve is the place to be. The park, measuring 25 acres (10.12 hectares), has scenic trails and is home to over 180 bird species. Aside from exciting leisure opportunities and attractions, there are a plethora of hotels in and around the city. If you’re looking to stay for quite some time in the city, scroll down for the top extended stay hotels near Winchester, Virginia.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on October 29, 2025.
1. Candlewood Suites Winchester, an IHG Hotel (from USD 118)
Enjoy a restful long-term stay at this modern hotel. Here, you’re free to enjoy some quiet time in the picnic area and have an outdoor cookout using the barbeque grills. The in-house gym is well-equipped and lures those looking to burn some extra calories.
Inside each guest room is a kitchenette that can come in handy when you don’t want to venture off-site for food. Free self-parking, a 24-hour business center, and laundry services are other perks for guests.
Candlewood Suites Winchester by IHG
Address: 1135 Millwood Pike
1.78 km (1.2 mi) from Jim Barnett Park
2. TownePlace Suites by Marriott Winchester (from USD 116)
Choose this hotel for your extended break near Winchester. It’s in a prime location near Apple Blossom Mall and Jim Barnett Park. During your time here, you can decompress in the outdoor pool, accessible from 6 am to 10 pm. In the morning, take full advantage of their free continental breakfast and start your day on a full stomach.
All rooms have kitchens, convenient should you wish to put together your own meals. Guests will also appreciate the in-room refrigerators and microwaves. Make the most of the dry cleaning services and keep your clothes fresh.
TownePlace Suites by Marriott Winchester
Address: 170 Getty Ln
2.51 km (1.6 mi) from Jim Barnett Park
3. TownePlace Suites by Marriott Front Royal (from USD 147)
This 3-star hotel is prepared to make your extended holiday in Virginia as pleasant as possible. As a complimentary continental breakfast is offered on site, guests don’t have to venture elsewhere for the same. The outdoor pool is open from June to August and is a great place to enjoy the sun.
The hotel’s barbecue grills and in-room kitchens are there to help you with preparing meals. In the afternoon, feel free to unwind in the picnic area. Other thoughtful perks available on the property include a 24-hour gym and internet.
TownePlace Suites by Marriott Front Royal
Address: 5 Caroline Drive
23.41 km (14.6 mi) from Jim Barnett Park
4. Home2 Suites by Hilton Charles Town (from USD 170)
Relish Virginia’s outstanding hospitality by staying at this hotel. This property offers a lot of amenities to make your prolonged stay more enjoyable. Among its highlights is an indoor pool, available from 8 am to 11 pm. On slow days, you can laze on the terrace or stretch your muscles in the 24-hour gym.
All rooms here have modern kitchens, so come prepared to rustle up any meal of your desire. The kitchens feature full-sized refrigerators and dishwashers. Better yet, a free continental breakfast is available each morning.
Home2 Suites by Hilton Charles Town
Address: 70 Jefferson Crossing Way
30.21 km (18.8 mi) from Jim Barnett Park
5. Homewood Suites by Hilton Leesburg (from USD 145)
This hotel boasts a prime location near tourist sites such as Leesburg Premium Outlets, Village at Leesburg, and Tally Ho Theater. While here, put together many delicious meals in the in-room kitchen with full-sized refrigerators and stovetops. Also, don’t hesitate to take advantage of the in-house barbecue grills and free grocery shopping service.
The swimming pool is a nice spot to beat the summer heat. With free Wi-Fi and 32-inch LCD TVs available in all rooms, you don’t have to get bored while indoors. Dogs and cats are welcome, however, only two are permitted per room.
Homewood Suites by Hilton Leesburg
Address: 115 Fort Evans Rd Ne
53.22 km (33.1 mi) from Jim Barnett Park
Enjoy a fun yet restful vacation near Winchester
If you are looking to explore a new destination and create beautiful memories, Winchester is the perfect place for you. With its vibrant culture, delicious culinary offerings, and restful accommodations, the city guarantees a great holiday. Settle in any of the above hotels and experience a restful long-term vacation.
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