Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $695, price is now $563 per person
$563
per person
Mar 14 - Mar 19
found 8 hours ago
Roundtrip non-stop flight included
Medford (MFR) to St. Louis (STL)
This apartment features a garden, express check-out, and laundry facilities. The front desk is staffed around-the-clock and barbecue grills are on offer.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $911, price is now $585 per person
$585
per person
Mar 14 - Mar 19
found 8 hours ago
Roundtrip non-stop flight included
Medford (MFR) 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.
The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $949, price is now $759 per person
$759
per person
Mar 14 - Mar 19
found 8 hours ago
Roundtrip non-stop flight included
Medford (MFR) to St. Louis (STL)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.
The Cheshire

The Cheshire

4 out of 5
Price was $929, price is now $760 per person
$760
per person
Mar 14 - Mar 19
found 8 hours ago
Roundtrip non-stop flight included
Medford (MFR) 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 $862, price is now $710 per person
$710
per person
Mar 14 - Mar 19
found 8 hours ago
Roundtrip non-stop flight included
Medford (MFR) 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
Jan 7 - Jan 8
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
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
$81 nightly
The price is $93 total per night
$93 total
Jan 15 - Jan 16
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
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 out of 5
2401 Holliday Ln Jacksonville IL
Free Cancellation
$80 nightly
The price is $89 total per night
$89 total
Jan 18 - Jan 19
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
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
$56 nightly
The price is $63 total per night
$63 total
Feb 6 - Feb 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
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
$83 nightly
The price is $92 total per night
$92 total
Jan 11 - Jan 12
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
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
$55 nightly
The price is $63 total per night
$63 total
Jan 25 - Jan 26
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
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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).

Photos of local treasures

Browse Winchester vacation photos for more inspiration