Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $463, price is now $381 per person
$381
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and express check-out are also provided.
Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was $562, price is now $425 per person
$425
per person
Oct 16 - Oct 19
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free parking, a terrace, and a snack bar/deli are also offered.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $546, price is now $422 per person
$422
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
Free WiFi in public areas, express check-in, and express check-out are available at this aparthotel. Luggage storage, laundry facilities, and a virtual front desk are also on offer.
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
Price was $955, price is now $763 per person
$763
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Hampton Inn & Suites Cranberry Pittsburgh

Hampton Inn & Suites Cranberry Pittsburgh

2.5 out of 5
Price was $780, price is now $652 per person
$652
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
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 continental breakfast and free self parking.

Top Chester hotels deals

The Piedmont Cabin 2 bed, 1.5 bath

The Piedmont Cabin 2 bed, 1.5 bath

Chester WV
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This vacation home includes a garden and laundry facilities.
Kitchen
Washer
The Auburn Home - LPM

The Auburn Home - LPM

Chester WV
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This vacation home includes a garden and barbecue grills.
Kitchen
Washer
Secluded Wilderness & Spa On Historic 2k Acre Wild Life Area

Secluded Wilderness & Spa On Historic 2k Acre Wild Life Area

Chester WV
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A hot tub is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd Coraopolis PA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $97 total per night
$97 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
710 Aviation Avenue Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $210 total per night
$210 total
Sep 6 - Sep 7
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Pittsburgh Airport Inn and Suites

Pittsburgh Airport Inn and Suites

2.5 out of 5
8514 University Boulevard Coraopolis PA
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $95 total per night
$95 total
Sep 20 - Sep 21
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and a fireplace in the lobby. Enjoy freebies like buffet breakfast and a roundtrip airport shuttle A 24-hour business center, express check-out, and luggage storage are also on offer.
Breakfast included
Free airport shuttle
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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

Tomlinson Run Lake

Commune with nature and explore the great outdoors at Tomlinson Run Lake during your travels in Chester. Amble around the area's riverfront or visit its casinos.
See properties

Frequently asked questions

How much are vacation packages to Chester?
With deals starting as low as $381, flight and hotel packages are an excellent way to stretch your travel budget. Watch out Chester — here you come!
Where can I get the best vacation package deals for Chester?
Travelocity is where to go to score a terrific Chester package deal. Select from 400 air carriers and 1,000,000 properties all over the world and put together a vacation package that fits your style. With so many options at hand, it's time to start booking your next big getaway.
Why should I book my Chester vacation package with Travelocity?
Whether you're planning a month-long vacation or a last-minute weekend escape, we have lots of alluring destinations to choose from at a good price. In addition, we offer 24/7 support, superb service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation now.
Can I save money on my Chester car rental if I bundle it with hotels and flights?
Bundling your hotel, flight and car into a Chester vacation package is a great way to land the best deal. Plus, having your own set of wheels gives you total freedom to find your way to all the landmarks you want to see. Situated 90 mi from Chester, Geneva State Park is one attraction that should be on your can't-miss list. Fasten your seat belt and make a day trip of it.
Which airport is best for Chester?
Many travelers arrive at Pittsburgh Intl. Airport (PIT). Once you've landed and grabbed your luggage, head 18 mi northwest to reach central Chester. Akron-Canton Airport (CAK) is your other choice, 50 mi from the center of the city.
What is there to do in Chester?
The Mountaineer Race Track & Gaming Resort deserves to be on your itinerary. After you've crossed off this top attraction, wander through the streets of Chester and experience what makes this fantastic place tick.
Where should I stay when visiting Chester?
The Secluded Wilderness & Spa - Near Mountaineer & Star Lake - 30 Min Pitts Airport is the first choice of many travelers. Book as soon as possible before it's too late.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A steel bridge spanning a river with a hilly landscape in the background.
A large teapot-shaped structure labeled "World's Largest Teapot" in Chester, WV.