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 $89. In comparison, May is the most expensive month, with prices at $124.
What is the cheapest day of the week to book a hotel in Winchester?
Sunday offers the lowest rates in Winchester, with an average nightly price of $99. The highest prices are found on Saturday, with average rates at $132.
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.
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 29% 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
If you’re looking for a cheap hotel in Washington, D.C., you should consider visiting during the low season. You'll find cheaper hotels in Washington, D.C. in November and January.
Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Washington, D.C. if you stay on a Sunday. The opposite is true for, Saturday, which is usually the most expensive day.
The cheapest 3-star hotel room in Washington, D.C. found on KAYAK in the last 2 weeks was $89, while the most expensive was $154.
How long should you stay? KAYAK users usually book their hotel in Washington, D.C. for 3 days.
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.
The George Washington - A Wyndham Grand Hotel is one of the best hotels in Winchester for family travelers in the city. The hotel has interconnected rooms which allow you to watch the children and special diet menus on request. You will also benefit from the laundry services and a playground for the kids.
Travelers prone to experiencing allergies can make their reservations at Holiday Inn Winchester Se-Historic Gateway. Located about 2.1 miles from the city center, the hotel offers allergy-free rooms, non-feather pillows, and designated smoking areas for guests.
If you plan on visiting the Winchester Little Theatre, you should make a reservation at the Quality Inn Hotel. Located about 2.5 miles from the city center, the hotel offers guests access to the theater about 2.7 miles away. You can also visit the Handley Regional Library and the Patsy Cline Historic House.
If you travel with your pet to Winchester, you can book a room at the Tru by Hilton Winchester Hotel. The hotel allows two pets with a maximum weight of 75 lbs. You will, however, be charged an additional fee for each pet.
If you are a working mother traveling with a young baby, the TownePlace Suites by Marriott Winchester Hotel is best suited for you. The hotel offers cribs for the baby and babysitting or childcare services. The hotel also offers room service and complimentary breakfast.
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.
Is there a wheelchair-accessible hotel in Winchester?
Yes. The SpringHill Suites by Marriott Winchester Hotel has some of the best amenities a wheelchair user will most definitely appreciate. Located about 3.1 miles from the city center, the hotel has easy access as the entire unit is wheelchair accessible. The bathrooms are fitted with roll-in showers, adapted baths, and a shower chair. The toilets also have grab rails for balance and stability for more convenience.
Which would be the best hotel for art and history-loving guests in Winchester?
The Comfort Inn and Suites hotel is located about 4.9 miles from the city center and offers access to sites and attractions that will be enjoyed by art and history lovers. The hotel is approximately 4.4 miles from the Patsy Cline Historic House and 3.9 miles from Abram’s Delight. If you love museums, the Shenandoah Valley Discovery Museum and the Old Court House Museums are located about 4.6 and 4.8 miles, respectively, from the hotel.
Can I get a hotel in Winchester suitable for a traveling business person?
Yes, you can. The Hilton Garden Inn Winchester Hotel is among the best hotels for traveling business people. The hotel offers meeting and banquet facilities if you have scheduled business meetings. You can also access the conference halls within the hotel as a guest. Located about 0.4 miles from the Apple Blossom Mall, the hotel has a 24-hour front desk, room service, and express check-out services.
Which hotel is best for guests to enjoy outdoor sports and activities in Winchester?
The Hampton Inn Winchester N/Conference Center, VA, is among the best choices available if you are visiting Winchester and enjoy outdoor sports and activities. The hotel allows the guests to participate in activities such as hiking and fishing. Located about 1.2 miles from the city center and 0.9 miles from Jim Barnet Park, the hotel also allows you to enjoy horse riding, golf, and skiing.
Which amenities do KAYAK users look for when booking a hotel in Winchester?
The most sought-after amenities KAYAK users looked for in their hotel in Winchester are: pet friendly and pool.
How do I find a hotel in central Winchester?
After you launch a hotel search on KAYAK, you can refine your research by neighborhood, 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 center.
How can I find hotels near me?
Take a look at our extensive hotel map to find the best hotels near you.
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