Winchester hotels

KAYAK searches hundreds of travel sites at once for hotels in Winchester, Virginia

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Winchester hotels

Discover the best prices by selecting your travel dates on KAYAK.

Most recommended Winchester hotels

Show all
Fairfield Inn & Suites by Marriott Winchester - Winchester - Lobby
Fairfield Inn & Suites by Marriott Winchester
Winchester, VA, United States
8.8Very Good(241)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 168+
Check availability
Motel 6 Winchester - Winchester - Bedroom
Motel 6 Winchester
Winchester, VA, United States
7.5Good(805)
Free Wi-Fi
Pet-friendly
Air conditioning
R1 377+
Check availability
La Quinta Inn & Suites by Wyndham Winchester - Winchester - Building
La Quinta Inn & Suites by Wyndham Winchester
Winchester, VA, United States
8.8Very Good(1574)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 212+
Check availability
Courtyard by Marriott Winchester Medical Center - Winchester - Lounge
Courtyard by Marriott Winchester Medical Center
Winchester, VA, United States
8.3Very Good(286)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 216+
Check availability
Holiday Inn Winchester Se-Historic Gateway - Winchester - Lounge
Holiday Inn Winchester Se-Historic Gateway
Winchester, VA, United States
8.6Very Good(798)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 046+
Check availability
TownePlace Suites by Marriott Winchester - Winchester - Lounge
TownePlace Suites by Marriott Winchester
Winchester, VA, United States
8.7Very Good(113)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 215+
Check availability
Sleep Inn & Suites - Winchester - Front desk
Sleep Inn & Suites
Winchester, VA, United States
7.3Good(1139)
Parking
Free Wi-Fi
Pool
Air conditioning
R1 692+
Check availability
Holiday Inn Express & Suites Winchester - Winchester - Patio
Holiday Inn Express & Suites Winchester
Winchester, VA, United States
8.6Very Good(340)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 683+
Check availability
Hampton Inn Winchester-University/Mall Area - Winchester - Pool
Hampton Inn Winchester-University/Mall Area
Winchester, VA, United States
8.6Very Good(194)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 699+
Check availability
Hilton Garden Inn Winchester - Winchester - Pool
Hilton Garden Inn Winchester
Winchester, VA, United States
8.8Very Good(179)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 985+
Check availability
Spark by Hilton Winchester - Winchester - Lobby
Spark by Hilton Winchester
Winchester, VA, United States
8.7Very Good(424)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 403+
Check availability
Super 8 by Wyndham Winchester VA - Winchester - Living room
Super 8 by Wyndham Winchester VA
Winchester, VA, United States
4.7Mediocre(571)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 281+
Check availability
The George Washington - A Wyndham Grand Hotel - Winchester - Lounge
The George Washington - A Wyndham Grand Hotel
Winchester, VA, United States
9.0Wonderful(863)
Free Wi-Fi
Pool
Air conditioning
R2 959+
Check availability
Country Inn & Suites by Radisson, Winchester, VA - Winchester - Building
Country Inn & Suites by Radisson, Winchester, VA
Winchester, VA, United States
8.2Very Good(1880)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 127+
Check availability
Travelodge by Wyndham Winchester - Winchester - Pool
Travelodge by Wyndham Winchester
Winchester, VA, United States
7.8Good(1836)
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 385+
Check availability
Candlewood Suites Winchester - Winchester - Building
Candlewood Suites Winchester
Winchester, VA, United States
8.7Very Good(217)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 417+
Check availability

Popular filters in Winchester hotels

Hotels with parking
Fairfield Inn & Suites by Marriott Winchester, La Quinta Inn & Suites by Wyndham Winchester and others
Find stays
Go to map

Search by stars

2+ stars3+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R1 062 - R1 471R1 471 - R1 881R1 881 - R2 291R2 291 - R2 682R2 682+ per night

Search by freebies

Free cancellationFree breakfastFree parkingFree internet
Useful Info

KAYAK’s insights for hotels in Winchester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winchester with confidence.

Which month has the cheapest hotel rates in Winchester?

Hotels are cheapest in Winchester in January, with average rates of R32 566. In comparison, May is the most expensive month, with prices at R43 431.

What is the cheapest day of the week to book a hotel in Winchester?

Monday offers the lowest rates in Winchester, with an average nightly price of R33 923. The highest prices are found on Friday, with average rates at R45 899.

How early should you book a hotel in Winchester?

Book at least 38 days before your stay begins to get the best price for your Winchester hotel.
Find deals

How much is a Winchester hotel?

Here are our most popular & best value hotels

Good to know

Low season

January

High season

May

Average price (weeknight)

R1 948

Average price (weekend night)

R2 284
Cheapest month to stay with an average 17% drop in price.
Most expensive month to stay with an average 11% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Winchester hotel deals

  • Those visiting Winchester to spend some time outdoors will love lodging near Jim Barnett Park or Shawnee Springs Preserve. Hilton Garden Inn Winchester conveniently lies less than a mile from Shawnee Springs Preserve and 0.9 miles from Jim Barnett Park. The hotel offers suites with upscale décor, pull-out sofas, and custom-designed beds alongside an indoor pool and a gym.
  • Visitors that wish to hit the golf range while visiting Winchester can book accommodation near public golf courses. TownePlace Suites by Marriott Winchester offers convenient stays 1.7 miles from Winchester Country club and 4.1 miles from Rock Harbor Golf Course. It offers relaxed suites with pull-out sofas and separate living rooms alongside a seasonal outdoor pool and a gym.
  • If you are visiting Winchester for business purposes, consider booking accommodation near the city's business centers. Holiday Inn Express & Suites Winchester lies 1.1 miles from Westside Professional Center and 2.8 miles from Plaza Executive Center. The hotel offers contemporary suites with pull-out sofas alongside an indoor pool and a fitness center.
  • Bird-watching enthusiasts will love staying near Abrams Creek wetlands Preserve. Travelodge Winchester lies less than 2 miles from the area offering furnished suites. Motel 6 Winchester offers rooms with wood floors and granite countertops 1.9 miles from the creek.
  • Visitors that wish to stay in parts of the city with more character can get accommodation near Old Town Winchester. The George Washington A. Wyndham Grand hotel lies 1.3 miles from the Museum of Shenandoah Valley, offering suites with fireplaces and Whirlpool tubs alongside an indoor pool and a spa. Tru by Hilton Winchester lies 3 miles from Old Town Winchester and 5 miles from the Museum of Shenandoah Valley offers a gym and a heated indoor pool.

FAQs when booking a hotel in Winchester

  • What are my options in scenic parts of Winchester?

    Regions of Winchester, known for having particularly stunning sceneries are near Winchester City Mill and Wolvesey Castle. Winchester Royal Hotel conveniently lies 0.4 miles from Wolvesey Castle and Winchester City Mill. The hotel offers suites with traditional décor and four-poster beds alongside free parking and a walled garden.

  • What are the best airport hotels in Winchester?

    Winchester Regional Airport serves the city. Sleep Inn & Suites lies 1.1 miles from the airport, offering suites with Whirlpool tubs, and pull-out sofas alongside a heated indoor pool. Super 8 by Wyndham Winchester lies 1.1 miles from the airport.

  • What are my options within walking distance of dining options?

    If you wish to avoid walking too far for dining options, consider getting accommodation near downtown, which hosts various local eateries. Candlewood Suites lies off I-81, offering casual suites alongside a fitness room near the city’s local eateries. SpringHill Suites by Marriott Winchester offers easy access to local restaurants, and it features an indoor pool and a gym.

  • What are the best options for families?

    Wingate by Wyndham Winchester and Quality Inn offer connecting rooms for visitors traveling with children. Country Inn & Suites by Radisson, Winchester offers activities for children with housekeeping services and extra cribs for toddlers.

  • How do I find a hotel in central Winchester?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Winchester districts. You can also do a search using the city map to choose a specific location, like Winchester city centre

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Winchester hotels with free parking?

    There are many hotels in Winchester that offer both parking and free parking. Popular choices among KAYAK users include Fairfield Inn & Suites by Marriott Winchester, La Quinta Inn & Suites by Wyndham Winchester and Courtyard by Marriott Winchester Medical Center.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each hotel.

Everything you need to know for your stay in Winchester

All hotels in Winchester

Winchester Hotel Deals. Search and compare hotels in Winchester. Find cheap hotel rooms in Winchester. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

Not what you’re looking for? Find thousands of other hotels, flights and car hire with KAYAK.