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.
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Save 100% on your flight
Price was $484, price is now $344 per person
$344
per person
Aug 27 - Aug 31
found 3 hours ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
7 indoor tennis courts, an indoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $731, price is now $348 per person
$348
per person
Aug 27 - Aug 31
found 3 hours ago
Roundtrip flight included
Denver (DEN) 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.
Residence Inn by Marriott St Louis Downtown

Residence Inn by Marriott St Louis Downtown

3 out of 5
Midtown
Save 100% on your flight
Price was $934, price is now $568 per person
$568
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to St. Louis (STL)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a grocery/convenience store are also offered.
Remodeled and Inviting Free EV

Remodeled and Inviting Free EV

2 out of 5
Price was $817, price is now $562 per person
$562
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.
The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $565, price is now $397 per person
$397
per person
Aug 27 - Aug 31
found 3 hours ago
Roundtrip flight included
Denver (DEN) 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
$60 nightly
The price is $68 total per night
$68 total
Jul 15 - Jul 16
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.
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
$90 nightly
The price is $100 total per night
$100 total
Jul 26 - Jul 27
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
$64 nightly
The price is $71 total per night
$71 total
Jul 14 - Jul 15
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.
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Free Cancellation
$68 nightly
The price is $75 total per night
$75 total
Jul 20 - Jul 21
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.
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
$77 nightly
The price is $86 total per night
$86 total
Jul 26 - Jul 27
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.
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
$58 nightly
The price is $66 total per night
$66 total
Jul 26 - Jul 27
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.
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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 $344. 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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