Hotels in Winchester

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Knights Inn Jacksonville East Morton Ave
Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (167 reviews)
This budget-friendly motel offers continental breakfast starting at 5:30 AM daily and complimentary self parking. Located near the Small Eli Ferris Wheel and Jacksonville Community Park, the accommodation includes round-the-clock front desk assistance.
The price is $65
$74 total
includes taxes & fees
May 12 - May 13
Knights Inn Jacksonville East Morton Ave
Jacksonville Inn & Suites
Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.6 out of 10, Good, (14 reviews)
The price is $66
$73 total
includes taxes & fees
May 12 - May 13
Jacksonville Inn & Suites
Sleep Inn & Suites South Jacksonville
Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (673 reviews)
Experience Jacksonville from this comfortable hotel with an indoor pool and fitness center. Located near Prairie Land Heritage Museum and Jacksonville Community Park, guests love the friendly staff and free breakfast, WiFi, and parking.
The price is $83
$92 total
includes taxes & fees
May 21 - May 22
Sleep Inn & Suites South Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (460 reviews)
This quiet hotel features a 24-hour fitness center and refreshing indoor pool, perfect for unwinding after exploring nearby Prairie Land Heritage Museum. Enjoy complimentary breakfast, WiFi, and parking during your peaceful Jacksonville stay.
The price is $94
$104 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Quality Inn Jacksonville near I-72
Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (461 reviews)
Tucked near I-72, this welcoming hotel offers free breakfast, WiFi, and parking. Swim year-round in the indoor pool or maintain your workout in the fitness center. Just minutes from Prairie Land Heritage Museum and Jacksonville Community Park.
The price is $64
$71 total
includes taxes & fees
Jun 10 - Jun 11
Quality Inn Jacksonville near I-72
Super 8 by Wyndham Jacksonville
Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (635 reviews)
Discover a serene stay at this Jacksonville motel, known for its peaceful atmosphere and helpful staff. Wake up to a continental breakfast, use free Wi-Fi, and enjoy complimentary parking. Close to Prairie Land Heritage Museum and Community Park.
The price is $57
$65 total
includes taxes & fees
May 21 - May 22
Super 8 by Wyndham Jacksonville
Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (782 reviews)
The price is $75
$85 total
includes taxes & fees
May 12 - May 13
Best Western Jacksonville Inn
Hampton Inn Jacksonville
Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (517 reviews)
Wake up to a peaceful morning and complimentary breakfast at this quiet Jacksonville haven. The helpful staff ensures a smooth stay while you explore nearby Prairie Land Heritage Museum. After sightseeing, unwind in the indoor pool or fitness center.
The price is $109
$124 total
includes taxes & fees
May 14 - May 15
Hampton Inn Jacksonville
Monroe Street Suites
Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (61 reviews)
Minutes from Pittsfield's historic attractions, this welcoming hotel combines comfort with practicality. Enjoy free WiFi and parking while exploring nearby John Greene Shastid House and Pike County Historic Museum. Daily housekeeping ensures a fresh, relaxing stay.
The price is $98
$108 total
includes taxes & fees
May 12 - May 13
Monroe Street Suites
William Watson Hotel
William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (355 reviews)
Discover small-town hospitality at this historic hotel near Pike County Historic Museum and John Greene Shastid House. Work out in the fitness center, grab a bite at the deli, and enjoy convenient free parking and 24-hour front desk service.
The price is $85
$93 total
includes taxes & fees
May 12 - May 13
William Watson Hotel
Green Acres Hotel
Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (145 reviews)
Experience tranquil comfort at this welcoming hotel near King Park and John Greene Shastid House. Start your day with a continental breakfast before exploring Pittsfield. Return to modern rooms with free WiFi and convenient parking.
The price is $117
$129 total
includes taxes & fees
May 12 - May 13
Green Acres Hotel
Rodeway Inn Pittsfield
Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (132 reviews)
Escape to this Pittsfield hotel offering free WiFi, parking, and daily on-the-go breakfast. Explore nearby King Park and John Greene Shastid House while enjoying convenient amenities that make your stay effortless and comfortable.
The price is $58
$64 total
includes taxes & fees
May 24 - May 25
Rodeway Inn Pittsfield
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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Frequently asked questions

Can I book a refundable hotel in Winchester?
If you need the flexibility to change your travel plans to Winchester, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my visit?
The warmest months in Winchester are usually July and August with an average temp of 73°F. January and February are the chilliest months when the average temp is 35°F. The rainiest months are May and April.
Why should I book my Winchester accommodation with Hotels.com?
There are plenty of reasons to book your Winchester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.