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 $717, price is now $519 per person
$519
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $844, price is now $563 per person
$563
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,862, price is now $1,331 per person
$1,331
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the steam room and perks like free WiFi. Valet parking, a 24-hour business center, and a coffee shop are also offered.
The Inn on Negley

The Inn on Negley

4 out of 5
Shadyside
Price was $842, price is now $666 per person
$666
per person
Nov 15 - Nov 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
This inn doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, a garden, and a computer station are also on offer.
Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $776, price is now $625 per person
$625
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
Free WiFi in public areas, a communal living room, and express check-in are available at this hotel. Enjoy the free self-serve breakfast each morning. Express check-out, luggage storage, and laundry facilities are also on offer.

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.
The Auburn Home - LPM

The Auburn Home - LPM

Chester WV
Get rates
This vacation home includes a garden and barbecue grills.
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.
Hot Tub
Kitchen
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
$80 nightly
The price is $91 total per night
$91 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet 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.
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
$199 nightly
The price is $227 total per night
$227 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.
Pool
Free airport shuttle
Wyndham Garden Pittsburgh Airport

Wyndham Garden Pittsburgh Airport

3 out of 5
1 Industry Lane Pittsburgh PA
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $83 total per night
$83 total
Sep 29 - Sep 30
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby and express check-out are also provided.
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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 $519, 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.