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 $865, price is now $547 per person
$547
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $992, price is now $758 per person
$758
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
A 24-hour gym, valet parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A hair salon, dry cleaning, and luggage storage are also on offer.
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was $1,266, price is now $995 per person
$995
per person
Jul 2 - Jul 5
found 22 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Pittsburgh (PIT)
Free WiFi in public areas, a garden, and express check-in are available at this vacation home. A free airport shuttle is offered as well. Express check-out, a computer station, and luggage storage are also on offer.
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $1,140, price is now $909 per person
$909
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Pittsburgh (PIT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a grocery/convenience store, and a lobby fireplace are also offered.
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,624, price is now $1,315 per person
$1,315
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Pittsburgh (PIT)
This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a computer station 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.
Kitchen
Washer
The Auburn Home - LPM

The Auburn Home - LPM

Chester WV
Get rates
This vacation home includes a garden and barbecue grills.
Kitchen
Washer
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
$179 nightly
The price is $204 total per night
$204 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and express check-in are also offered.
Free airport shuttle
Pet friendly
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
$82 nightly
The price is $94 total per night
$94 total
Apr 26 - Apr 27
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
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
$72 nightly
The price is $82 total per night
$82 total
Apr 19 - Apr 20
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A fireplace in the lobby and express check-out are also provided.
Breakfast included
Parking included
Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
9600 University Blvd Coraopolis PA
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $156 total per night
$156 total
Apr 26 - Apr 27
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 perks like free self parking.
Pool
Hot Tub
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See all available properties in Chester
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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.

Popular places to visit

Mountaineer Casino Resort

Why not try your luck with a visit to Mountaineer Casino Resort during your time in Chester? Take some time to visit the casinos in this family-friendly area.

Mountaineer Casino Resort

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.

Tomlinson Run Lake

Pleasant Hills Golf Course

Enjoy a round of golf in Chester at Pleasant Hills Golf Course. Amble around the area's riverfront or visit its casinos.

Pleasant Hills Golf Course

Frequently asked questions

How much are vacation packages to Chester?
With deals starting as low as $547, 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

Aerial of Jennings Randolph Memorial Bridge - US Route 30 - Ohio River - East Liverpool, Ohio & Chester, West Virginia
Chester