Deals on vacations and trips to Winchester

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Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $685, price is now $563 per person
$563
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $1,235, price is now $620 per person
$620
per person
Jun 10 - Jun 13
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was $911, price is now $743 per person
$743
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to St. Louis (STL)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking. Self parking, dry cleaning, and luggage storage are also offered.
The Cheshire

The Cheshire

4 out of 5
Price was $741, price is now $604 per person
$604
per person
Jul 30 - Aug 2
found 8 hours ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free English breakfast each morning.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $745, price is now $609 per person
$609
per person
Jul 30 - Aug 2
found 8 hours ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 6 conference rooms, along with free WiFi in public areas. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.

Top Winchester hotels deals

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $85 total per night
$85 total
May 12 - May 13
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A business center, express check-out, and laundry facilities are also on offer.
Pool
Breakfast included
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $92 total per night
$92 total
May 21 - May 22
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like local cuisine breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$57 nightly
The price is $65 total per night
$65 total
May 21 - May 22
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Breakfast included
Pet friendly
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $69 total per night
$69 total
May 18 - May 19
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Free Cancellation
$64 nightly
The price is $71 total per night
$71 total
Jun 9 - Jun 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $124 total per night
$124 total
May 14 - May 15
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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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.

Frequently asked questions

How much are vacation packages to Winchester?
You'll be surprised — you can unwind in Winchester for as low as $563. Let Travelocity save you money and time with our amazing vacation packages. With hotels, flights and experiences all available at our one-stop shop, what are you waiting for?
Where can I get the best vacation package deals for Winchester?
Scoring the perfect package deal to Winchester is a piece of cake with Travelocity. With access to 400 airlines and 1,000,000 properties worldwide, you'll have loads of choice when it comes to your hotels and flights.
Why should I book my Winchester vacation bundle with Travelocity?
Fantastic savings, countless thrilling destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.
Will I save money on my Winchester car rental if I combine it with hotels and flights?
Bundling your car, flight and hotel into a Winchester vacation package is a great way to score an incredible deal. Plus, having your own set of wheels gives you absolute freedom to make your way to all those famous sights you're itching to explore. Sitting 70 mi away from Winchester, Busch Stadium is one attraction that should be on your agenda. Load up the car and make a day trip of it.
What is the best time of year to go to Winchester?
March, May and July are the most popular months to visit, while November, December and January are generally quieter. If your budget is limited, you'd be better off visiting around . is generally regarded as the most costly time of year to drop by.
Which airport is best for Winchester?
Lambert-St. Louis Intl. Airport (STL), around 60 mi south of inner Winchester, is probably where you'll fly into. Your other choices are Quincy Regional-Baldwin Field Airport (UIN) (45 mi away from central Winchester) and Abraham Lincoln Capital Airport (SPI) (45 mi away from central Winchester).

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