Deals on vacations and trips to Chester

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Elimwood Hotel, a Ramada by Wyndham

Elimwood Hotel, a Ramada by Wyndham

3 out of 5
Riverport
Price was $464, price is now $357 per person
$357
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to St. Louis (STL)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, along with the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,055, price is now $670 per person
$670
per person
Nov 5 - Nov 8
found 14 hours ago
Roundtrip flight included
Baltimore (BWI) 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.
Landing Furnished Apartments - Central West End

Landing Furnished Apartments - Central West End

3.5 out of 5
Central West End
Save 100% on your flight
Price was $740, price is now $569 per person
$569
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to St. Louis (STL)
This apartment features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, barbecue grills, and a virtual front desk are also on offer.
The Cheshire

The Cheshire

4 out of 5
Price was $860, price is now $678 per person
$678
per person
Nov 5 - Nov 8
found 14 hours ago
Roundtrip flight included
Baltimore (BWI) 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.
Hotel Indigo St Louis - Central West End by IHG

Hotel Indigo St Louis - Central West End by IHG

3.5 out of 5
Central West End
Price was $552, price is now $445 per person
$445
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to St. Louis (STL)
This Art Deco hotel features 4 restaurants, a bar/lounge, and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Self parking, a coffee shop, and express check-in are also offered.

Top Chester hotels deals

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street Chester IL
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $86 total per night
$86 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Baymont by Wyndham Festus

Baymont by Wyndham Festus

3 out of 5
1200 W. Gannon Drive Festus MO
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $76 total per night
$76 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
1001 Veterans Blvd Festus MO
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel 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. There's a gym on site, and a 24-hour front desk and a convenience store are also provided.
Silo Farm Haus- located in the heart of wine country!

Silo Farm Haus- located in the heart of wine country!

Ste. Genevieve MO
$331 nightly
The price is $370 total per night
$370 total
Aug 28 - Aug 29
Total with taxes and fees
This vacation home features laundry facilities.
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

2 out of 5
7555 State Hwy Y French Village MO
$133 nightly
The price is $151 total per night
$151 total
Aug 31 - Sep 1
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St Perryville MO
Free Cancellation
$97 nightly
The price is $111 total per night
$111 total
Sep 3 - Sep 4
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.
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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.

Stay near popular Chester attractions

Popeye Museum

9.4/10 (10 reviews)
You can browse the exhibits at Popeye Museum, a museum with a story of its own, during your travels to Chester. Discover the area's museums and shops.
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Frequently asked questions

How much are vacation packages to Chester?
Prepare to be surprised — you can recharge your batteries in Chester for only $357. Allow Travelocity to save you money and stress with our excellent vacation packages. With experiences, hotels and flights all ready to go at our one-stop shop, what's stopping you?
How long should my Chester vacation be?
Generally, people spend 2 nights in Chester. However, that mightn't be nearly enough time for you. If you're eager to see some of the area's off-the-beaten-path treasures, how about adding another few nights to your itinerary?
Where can I get the best vacation package deals for Chester?
It's hard to look past Travelocity when it comes to crafting your Chester package deal. There are at least 400 partner airlines and 1,000,000 worldwide properties to select from. Lock in your trip now and get ready to tick another exciting destination off your must-see list.
Why should I purchase my Chester vacation bundle via Travelocity?
We make traveling the world easy. Whether you're looking for an amazing new place to wander around or want to make sure you get the best price on offer, we've got your back. Our 24/7 customer support, quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Will I save money on my Chester car rental if I book it with my hotel or flight?
With a Chester vacation package, you can bundle your hotel, car and flight bookings and save tons. If you want to discover the best of this awesome region, why not head to Busch Stadium? This top attraction is 55 mi from Chester. With a rental car, you'll be there in no time.
Which airport is best for Chester?
There are two options for jetting to Chester, starting with Williamson County Regional Airport (MWA). It's roughly 45 mi from the center of the city, while Cape Girardeau Municipal Airport (CGI) is 50 mi away from central Chester.
What is there to do in Chester?
You'll sense an undeniable magic as you wander the streets of Chester. Popeye Museum and Elzie C. Segar Memorial Park are just two famous attractions that entice visitors to this wonderful city, so put them at the top of your itinerary.
Where should I stay when visiting Chester?
The Best Western Chester Hotel is the first choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A steel bridge over a river with a white boat.
A large, single-story house with a covered porch and a staircase leading to the entrance.

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