Winchester Hotels

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14 Aug - 15 Aug
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15 Aug - 16 Aug
This weekend
15 Aug - 17 Aug
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Top 10 trending Winchester hotels

Knights Inn Jacksonville East Morton Ave
Exterior

Knights Inn Jacksonville East Morton Ave

2.0 star property
6.8 out of 10, (163)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
The price is €63
includes taxes & fees
14 Sept - 15 Sept
Knights Inn Jacksonville East Morton Ave
Baymont by Wyndham Jacksonville
1 bedroom, desk, iron/ironing board, cots/infant beds

Baymont by Wyndham Jacksonville

2.5 star property
7.0 out of 10, Good, (822)
"Housekeeping did a marvelous job!"
The price is €56
includes taxes & fees
14 Sept - 15 Sept
Baymont by Wyndham Jacksonville
Sleep Inn & Suites
Exterior

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (557)
"The beds/pillows here are so comfortable. Clean and convenient rooms at a great price."
The price is €76
includes taxes & fees
14 Sept - 15 Sept
Sleep Inn & Suites
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Exterior

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
7.8 out of 10, Good, (411)
"Staff is polite and took care of our needs. Clean, quiet room. Nice breakfast, will stay here again. "
The price is €61
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Quality Inn Jacksonville near I-72
Lobby

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (391)
"Staff very nice and very friendly "
The price is €73
includes taxes & fees
14 Sept - 15 Sept
Quality Inn Jacksonville near I-72
Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (10)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Villa DeWolf
Super 8 by Wyndham Jacksonville
Lobby

Super 8 by Wyndham Jacksonville

2.0 star property
8.2 out of 10, Very good, (594)
"Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again"
The price is €54
includes taxes & fees
14 Sept - 15 Sept
Super 8 by Wyndham Jacksonville
Best Western Jacksonville Inn
Indoor pool

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very good, (692)
"Very nice room. Was able to park right outside our room. Very close to lots of food options."
The price is €73
includes taxes & fees
14 Sept - 15 Sept
Best Western Jacksonville Inn
Hampton Inn Jacksonville
Restaurant

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (467)
"Will go back again"
The price is €82
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn Jacksonville
Augustus Lodge Bed & Breakfast
Exterior

Augustus Lodge Bed & Breakfast

2.0 star property
The price is €543
includes taxes & fees
14 Sept - 15 Sept
Augustus Lodge Bed & Breakfast
William Watson Hotel
Breakfast meal

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (330)
"Always my Go-to place to stay in Pittsfield! Great staff, clean, comfortable, and location. Some rooms do not have windows so are really dark inside. But overall great place to stay!!"
The price is €80
includes taxes & fees
11 Sept - 12 Sept
William Watson Hotel
Green Acres Hotel
Lobby sitting area

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (134)
"Wonderful stay - was staying with a number of family members and it all worked out"
The price is €93
includes taxes & fees
13 Sept - 14 Sept
Green Acres Hotel
Rodeway Inn
Free daily on-the-go breakfast

Rodeway Inn

2.0 star property
7.0 out of 10, Good, (118)
"They really should attach the drain cover to the shower drain. Somebody could get seriously injured. Being a tile guy, looking around really had me laughing at the workmanship. The manager was a pretty cool guy, the room was fine, air conditioner worked great. Never went to the continental breakfast, i did see some little Debbie items"
The price is €55
includes taxes & fees
1 Sept - 2 Sept
Rodeway Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Winchester

Check out Morgan County Fairgrounds and Lake Jacksonville—just a couple of the sights around Winchester.

See all hotels in Winchester

Top Winchester Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Nice comfortable place and close to family "
Robert 1-night trip
Posted 9 days ago
William Watson Hotel

Frequently asked questions

Where is the best place for a stay in Winchester?

Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Super 8 by Wyndham Jacksonville and Best Western Jacksonville Inn. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This holiday home rental outside of Winchester is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes! The majority of hotel room reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

Best Western Jacksonville Inn: Features free full breakfast, a pool and free self-parking. Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel and Hampton Inn Jacksonville are two additional hotels with an on-site pool. View all hotels with pools in Winchester.

How is it to stay in Winchester?

Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 35 hotels and other accommodation options in the surrounding area. Find out more about Winchester.

What is there to see in Winchester?

Places to visit in the wider area include Morgan County Fairgrounds, Lake Jacksonville and Future Champions Sport Complex. You'll also find Old Orchard Country Club and Governor Duncan Mansion in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.