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Winchester Vacation Packages

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Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Elimwood Hotel, a Ramada by Wyndham

Elimwood Hotel, a Ramada by Wyndham

3 out of 5
Price was $274, price is now $225 per person
$225
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this golf hotel in Maryland Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hollywood Casino Amphitheatre and Ameristar Casino St. Charles are located nearby.
The room was decently clean. The breakfast was alright, nothing too crazy but they had decent options. Beds are definitely more firm than I would like but we slept okay. Staff was helpful and straightforward.

Reviewed on Oct 16, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $609, price is now $309 per person
$309
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.

StayAtlas Retreat w/ Pool, Gym, Games, BBQ

StayAtlas Retreat w/ Pool, Gym, Games, BBQ

3 out of 5
Save 100% on your flight
Price was $3,821, price is now $3,011 per person
$3,011
per person
Dec 23 - Dec 30
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
Stay at this vacation home in St. Louis. Enjoy free WiFi, a garden, and in-room washers/dryers. Popular attractions St. Louis Union Station and St. Louis Zoo are located nearby.
The property was such a fun surprise- the neighborhood was a little sketchy, but it was great on the inside and the backyard... Great experience, fun complimentary toiletries, etc

Reviewed on Sep 25, 2026

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Price was $2,440, price is now $1,938 per person
$1,938
per person
Dec 23 - Dec 30
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
Stay at this B&B in Hermann. Enjoy free breakfast, free parking, and a garden.
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.

Reviewed on May 22, 2026

The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Price was $466, price is now $372 per person
$372
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this luxury hotel in St. Louis. Enjoy breakfast (surcharge), 24-hour room service, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Enterprise Center and St. Louis Union Station are located nearby.

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was $425, price is now $346 per person
$346
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this business-friendly hotel in Chesterfield. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions The J - Chesterfield Gym & Fitness Center and Chesterfield Amphitheater are located nearby.

The Cheshire

The Cheshire

4 out of 5
Price was $888, price is now $733 per person
$733
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this boutique hotel in Richmond Heights. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Louis Zoo and St. Louis Union Station are located nearby.

Hampton Inn St. Charles St. Peters

Hampton Inn St. Charles St. Peters

2.5 out of 5
Price was $359, price is now $297 per person
$297
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
Book a stay at this golf hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ameristar Casino St. Charles and Hollywood Casino Amphitheatre are located nearby.
Fantastic place to stay! The staff was amazing!

Reviewed on Oct 16, 2026

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Elimwood Hotel, a Ramada by Wyndham

Elimwood Hotel, a Ramada by Wyndham

3 out of 5
Riverport
Price was $274, price is now $225 per person
$225
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $609, price is now $309 per person
$309
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
Price was $466, price is now $372 per person
$372
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was $425, price is now $346 per person
$346
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,224, price is now $694 per person
$694
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
StayAtlas Retreat w/ Pool, Gym, Games, BBQ

StayAtlas Retreat w/ Pool, Gym, Games, BBQ

3 out of 5
Mount Pleasant
Save 100% on your flight
Price was $3,821, price is now $3,011 per person
$3,011
per person
Dec 23 - Dec 30
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
The Cheshire

The Cheshire

4 out of 5
Price was $1,176, price is now $931 per person
$931
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Price was $2,440, price is now $1,938 per person
$1,938
per person
Dec 23 - Dec 30
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 19 - Fri, Dec 4
ATL
Hartsfield-Jackson Atlanta Intl.
STL
Lambert-St. Louis Intl.
$75 Roundtrip, found 13 hours ago
$75
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to Lambert-St. Louis Intl., returning Fri, Dec 4, priced at $75 found 13 hours ago
Frontier Airlines
Wed, Dec 2 - Mon, Dec 14
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$80 Roundtrip, found 9 hours ago
$80
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Denver Intl. to Lambert-St. Louis Intl., returning Mon, Dec 14, priced at $80 found 9 hours ago
Allegiant Air
Fri, Oct 23 - Wed, Oct 28
PIE
St. Petersburg-Clearwater Intl.
BLV
MidAmerica-St. Louis
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Oct 23 from St. Petersburg-Clearwater Intl. to MidAmerica-St. Louis, returning Wed, Oct 28, priced at $111 found 6 days ago
Frontier Airlines
Mon, Nov 2 - Mon, Nov 16
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$113 Roundtrip, found 6 hours ago
$113
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Nov 2 from Dallas-Fort Worth Intl. to Lambert-St. Louis Intl., returning Mon, Nov 16, priced at $113 found 6 hours ago