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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $714, price is now $494 per person
$494
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Portland (PDX) 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 Cheshire

The Cheshire

4 out of 5
Price was $787, price is now $643 per person
$643
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) 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.
Landing Amazing 1bd, Yoga Studio, Gym

Landing Amazing 1bd, Yoga Studio, Gym

3 out of 5
DeBaliviere Place
Price was $875, price is now $734 per person
$734
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Portland (PDX) to St. Louis (STL)
This apartment features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking and a virtual front desk are also offered on site.
Fairfield Inn by Marriott St. Louis Collinsville, IL

Fairfield Inn by Marriott St. Louis Collinsville, IL

3 out of 5
Eastport
Price was $613, price is now $516 per person
$516
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to St. Louis (STL)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was $660, price is now $558 per person
$558
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Portland (PDX) to St. Louis (STL)
This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and outdoor pool, and unwind with a drink at the poolside bar.

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 6 - Jul 7
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
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 16 - Jul 17
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
$72 nightly
The price is $80 total per night
$80 total
Jul 11 - Jul 12
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
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
$89 nightly
The price is $99 total per night
$99 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
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
$86 nightly
The price is $95 total per night
$95 total
Aug 2 - Aug 3
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
$68 nightly
The price is $75 total per night
$75 total
Jul 12 - Jul 13
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
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 $494. 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