Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Jun 19 - Jun 21
Next weekend
Jun 26 - Jun 28

Where to stay in Winchester?

Desk, blackout drapes, iron/ironing board, free WiFi

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.6 out of 10, Good, (24 reviews)
The price is $66
$73 total
includes taxes & fees
Jul 1 - Jul 2
Jacksonville Inn & Suites
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (803 reviews)
The price is $60
$68 total
includes taxes & fees
Jun 18 - Jun 19
Best Western Jacksonville Inn
Hallway

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (65 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
Jun 18 - Jun 19
Monroe Street Suites
Standard Room, 2 Queen Beds | Desk, iron/ironing board, free cribs/infant beds, free WiFi

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (646 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
Jul 12 - Jul 13
Super 8 by Wyndham Jacksonville
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (137 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 $57
$63 total
includes taxes & fees
Jun 21 - Jun 22
Rodeway Inn Pittsfield
Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (526 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 $81
$93 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn Jacksonville
Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (699 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 $89
$99 total
includes taxes & fees
Jun 28 - Jun 29
Sleep Inn & Suites South Jacksonville
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (147 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 $131
$144 total
includes taxes & fees
Jun 18 - Jun 19
Green Acres Hotel
Exterior

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (172 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
Jun 18 - Jun 19
Knights Inn Jacksonville East Morton Ave
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (362 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
Jun 18 - Jun 19
William Watson Hotel
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (475 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
Jul 16 - Jul 17
Quality Inn Jacksonville near I-72
Exterior

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, (475 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 $92
$102 total
includes taxes & fees
Jul 16 - Jul 17
Holiday Inn Express Hotel & Suites Jacksonville by IHG
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.
View all properties

Check out reviews of Winchester hotels guests love

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"Tyler, Jenna, and the rest of the staff here always make us feel at home. great place to stay always clean and friendly. My company has stayed here several times while working the Jacksonville Area. Anytime Its available ill stay here wether it be business or personal trip. ill eventually get to know the rest of the staff.. keep up the good work guys."
Keith 3-night trip
Posted 4 hours ago
Sleep Inn & Suites South Jacksonville

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.