
Hotel Deals in Winchester from $54
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Property Name
Guest Rating
Stars
Cities
- Front Royal
- Middletown
- Stephens City
- Strasburg
- Winchester
Brands
- Country Inn & Suites Americas
- Fairfield Inn by Marriott
- Hampton Inn
- Hilton Garden Inn
- Holiday Inn Express
- Independent
- Motel 6
- Spark by Hilton
- Super 8
- TownePlace Suites by Marriott
Property Types
- Hotel
The staff were kind when I needed to switch rooms.
Convenience stop easy to access off the highway
Very large and clean rooms. Restaurants within walking distance.
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Location was nice. Staff friendly
The lobby was nice
Very friendly staff
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The man working up front was awesome
Nothing. Was p
Owners are very nice with some of the employees are rude as hell
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Staff is professional and pleasant.
Clean and modern
Very comfortable room and well appointed.
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Hotel employee in the restaurant was incredibly kind and an excellent server. She was first rate
Easy access ,cleanliness of hotel, staff was friendly. Hotel has a restaurant and bar inside .
great room, clean, quiet, nice staff, nice breakfast
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Quiet, clean and neat a lot of restaurants. Easy access to highway. Breakfast was decent.
The staff were friendly and welcoming.
The staff at the front desk was wonderful. And I like the option of having pet friendly rooms with hard surface floors.
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Convenient location
Price. Of course, when you're only paying #62.50, you shouldn't expect too much, however I did not expect cockroaches for dirty sheets. The front desk girl was wonderful though and immediately got us a new room.
staff was outstanding
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Newness and cleanliness.
The staff was phenomenally kind.
clean, good location
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Amenities. Roominess.
Location and stAff
It was close to the highway and quite clean.
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It was clean
Location, hot breakfast good and included, cleanliness.
Large rooms
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The hotel is relatively new.
There was a great breakfast in the morning and the hotel staff was very friendly.
Convenient location, breakfast included
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convenient to location needed. Food near by
I liked its close proximity to I-95. The hotel, in general, was tastefully appointed, conveniently located across from a Chil?s restaurant, and the staff was pleasant.
Clean, convenient, good "last min" pricing, good beds
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The small table in the room, mini fridge.
Water pressure in shower was great
The desk clerk was very nice, hotel was not got us and he helped with refund immediately
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the friendliness of the staff as soon as we entered. the ease of checking in and checking out
Located near our family.
Clean. Quiet. Comfortable.
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The breakfast was amazing for the whole family then 6-10 great times
I loved the cleanliness of the hotel and room.
Have stayed here many times in the past. Does seem as though maybe things are not being cleaned as regularly but still a good hotel.
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Cleanliness
Access to Interstate
Courteousstaff and very clean rooms.
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The pool and hot tub was fantastic.
Location. History
Big surprise! Loved the area and the hotel....This place has a big potential when combining local events, spas and programs during apple blossom, summer and fall seasons. Could also be an excellent winter holiday stay. The room and bed were fabulous.
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It?s was nice
The hotel is modern, beautifully maintained and nicely appointed. Every staff member I encountered, from guest services to housekeeping, were very friendly and welcoming. I had a great experience.
Clean. Friendly. Good breakfast.
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clean room
The price and the staff. The staff was very knowledgeable and helpful.
Location. That's it.
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Heat work good
Staff greeting us at entrance was very friendly and helpful.
Everything! Great amenities, friendly staff, nicely appointed rooms, clean, perfect location for me
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Clean. Quiet. Comfortable. Free EV charging.
Clean, easy access off the highway, congenial staff.
Clean rooms. Very polite staff! Amenities seemed adequate for the price of the room. Overall, the stay was enjoyable.
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Location was great. Place was clean. It¿s what you would expect from a Hampton Inn which is a little to above average. Rooms are fine. Can¿t go wrong is you¿re looking for a reasonably priced room for a short stay.
Amazing location. Everything you need is within walking distance. Staff is friendly and accommodating.
After a long day of driving I got what I needed...a very clean, comfortable room! Quite expensive, but I haven't traveled in sometime. I guess it is to be expected, still $---- to sleep?
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For a hilton not a whole alot.
Bed was comfortable.
Big Rooms and Location Pool
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The location was good. It was very close to the north entrance to Shenadoah National Park. Breakfast had good options - waffles, egg patties, sausage links, cereal, oatmeal, yogurt, juice, toast, danish rolls, muffins.
overall value
Parking lot was well lit at night.
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Cleanliness, fast check in
Breakfast was good. Beds were clean, hotel was nice
Friendliness of the front desk clerk at check in.
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The price
Staff was great the room was clean and well maintained. Much better than the Super 8 in town.
For an older style building the room was very nicely remodeled
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the hotel was clean and while it was a hotel buffet breakfast everything was clean, food was fresh and there was a good variety.
Staff, breakfast
Staff was responsive in changing our room and giving us an extra hour to check out.
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Night staff was fairly efficient. In room in less that 20 mins
Stevie was very nice
The location was convenient
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The bed was comfortable and the view was nice.
The cookies and the ambiance.
It was very clean, nice room.
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Disabled room was roomy and clean.
How quickly we were able to get in and out
Convince of the handicap room
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Where to stay in Winchester
Learn about the top neighbourhoods of Winchester
Home to Shenandoah University, this beautiful, historic area is known for its surrounding orchards (it's one of the largest apple export areas in the nation), as well as its charming downtown area, known as Old Town Winchester. Stroll Old Town's pedestrian walking mall - located in the middle of a 45-block National Historic District - and discover specialty shops, historic attractions, unique eateries and family activities along the way. Enjoy outdoor recreation options, vineyards and farm markets in the surrounding Shenandoah Valley region.
Price by Week Day
Average hotel price on weekends is around $100.
In Winchester, hotel prices fluctuate throughout the week, averaging just over $80 on Monday and dipping to around $80–$90 midweek. Prices rise to around $100 on Friday and hover near $100 on Saturday, before decreasing again on Sunday.
Price by Month
Lowest prices just over $80 in January, highest around $150–$160 in May.
In Winchester, hotel prices show notable variation throughout the year. The lowest monthly prices are observed in January at just over $80, while the highest are in May, around $150–$160. This indicates a peak in demand during the spring.
How far in advance should I book?
Prices range from around $93 to just over $200.
In Winchester, hotel prices tend to rise as the check-in date approaches. Three weeks prior, the best hotels are often fully booked. Last-minute bookings may see lower-quality hotels discounting prices, with pre-arrival prices ranging from around $93 to just over $200.
Price by Hotel Class
Most popular category: 2* hotel at just over $80.
In Winchester, the distribution of hotels by star rating shows a clear trend of increasing prices with higher ratings. The most popular category is 2*, priced just over $80. There is a noticeable jump in price to around $120 for 3* hotels.
Frequently Asked Questions
What are the typical check-in and check-out times for hotels in Winchester?
What taxes and mandatory fees apply to hotel stays in Winchester?
How do hotel prices in Winchester vary by season?
How do hotel neighborhoods in Winchester differ in price, safety, and accessibility?
What connectivity options are available for remote work in Winchester hotels?
How do cancellation policies for hotels in Winchester compare to advance purchase options?
How much do hotel prices spike during the Shenandoah Apple Blossom Festival?
Is hotel Wi-Fi reliable for remote work in Winchester?
Do hotels in Winchester charge extra for pets?
How accessible are hotels in Winchester for guests with mobility needs?
Are there common lodging scams or booking pitfalls specific to Winchester?
Top Tips
- Book your Winchester hotel 60 to 90 days before the Shenandoah Apple Blossom Festival in April, as Old Town and downtown hotels fill first and independent B&Bs fill fastest. During festival periods, some major chains may offer special rates, but stricter advance cancellation windows often apply; confirm current policies and any festival promotions when booking.
- Choose an Old Town Winchester hotel on or near Loudoun Street for walkable access to museums and restaurants within a 0.3-0.8 mile (5-15 minute) radius, helping you avoid short car trips and parking time. If you need step-free routes, check sidewalk accessibility details or contact the city for ADA compliance information.
- Request a room away from I-81 or US-11 when booking to reduce truck and highway noise, as many chain hotels are near these highways. Some brands offer soundproofed rooms or complimentary earplugs, so call ahead to confirm what noise-reducing features are available.
- For hospital visits, stay within 2 miles of Winchester Medical Center — hotels along Route 7/50 and Route 522 can save 8-20 minutes of local driving compared to downtown or I-81 properties. Ask hotels about medical rates, shuttle service availability, pet policies, and extended-stay options, which are often helpful for medical travelers.
- Use hotel on-site parking for overnight stays, as downtown street and municipal garage parking are time-restricted. Check whether parking is included in your rate or if you will pay an additional fee (typically $15), and confirm accessible parking availability if needed.
- Expect limited late-night public transit and ride-hail options in Winchester. Plan for a rental car, use a hotel shuttle if available, or confirm local taxi company hours for arrivals after midnight; ask hotels for contact details of licensed taxi operators for safety.
- If you need accessibility features, confirm step-free access or elevators when booking historic inns in Old Town, as these buildings often have stairs and narrow corridors. For ADA-compliant rooms in chain or large hotels, call to verify door widths, roll-in showers, or step-free entry at least 72 hours before arrival; check if the city offers a map of accessible venues.
- Use chain loyalty programs (Hilton, Marriott, Choice, or Best Western) for predictable benefits such as points, free breakfast, and clearer cancellation policies; actual perks may vary by loyalty tier. Some Winchester hotels run brand-specific promotions—ask about special point offers or local rate discounts at booking.
- Check the Shenandoah University calendar for weekends with events like commencement or home games, which drive local hotel demand. Book 30-45 days ahead for those periods, and if possible, refer to the university's official event schedule for key dates.
Hotels in Winchester
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- United States
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