Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
River City Casino & Hotel

River City Casino & Hotel

4 out of 5
Save 100% on your flight
Price was $559, price is now $430 per person
$430
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
This hotel features a casino, a nightclub, and 5 restaurants. Traveling on business? Take advantage of the business center, conference center, and conference space. Enjoy the 24-hour gym and perks like free self parking.
Residence Inn by Marriott St. Louis West County

Residence Inn by Marriott St. Louis West County

3 out of 5
Save 100% on your flight
Price was $1,163, price is now $699 per person
$699
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free full breakfast each morning.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $704, price is now $447 per person
$447
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Save 100% on your flight
Price was $664, price is now $461 per person
$461
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $831, price is now $604 per person
$604
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

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
Oct 20 - Oct 21
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
$88 nightly
The price is $98 total per night
$98 total
Nov 1 - Nov 2
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
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $81 total per night
$81 total
Oct 8 - Oct 9
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
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
$59 nightly
The price is $67 total per night
$67 total
Oct 18 - Oct 19
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
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 out of 5
2501 Holliday Lane Jacksonville IL
Free Cancellation
$89 nightly
The price is $99 total per night
$99 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Free Cancellation
$60 nightly
The price is $66 total per night
$66 total
Nov 6 - Nov 7
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
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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 $430. 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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