Chester Vacations from $353

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Your Chester Vacation

With one of our vacation packages to Chester, you'll find countless opportunities for relaxation and adventure. There's loads to experience, including its rich history and cultural experiences. Make your trip to Chester even more fun by including some sightseeing. Swarthmore College, Harrahs Casino and Racetrack and Widener University are among the big attractions you'll want to explore. Whatever your travel plans or budget, putting together a tailored Chester vacation is a cinch with Expedia.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
New Season Royals

New Season Royals

2 out of 5
Price was $525, price is now $353 per person
$353
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Philadelphia (PHL)
9.2/10 Wonderful! (157 reviews)

Casa De Miliki

Casa De Miliki

3 out of 5
South Philadelphia
Price was $6,950, price is now $3,793 per person
$3,793
per person
Dec 10 - Dec 14
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews

Tudor Place

Tudor Place

4 out of 5
Price was $4,572, price is now $2,888 per person
$2,888
per person
Dec 10 - Dec 14
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews

Orchard Way

Orchard Way

2 out of 5
Price was $3,326, price is now $2,111 per person
$2,111
per person
Dec 10 - Dec 14
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews

Tudor Lux

Tudor Lux

4 out of 5
Price was $6,601, price is now $4,573 per person
$4,573
per person
Dec 10 - Dec 14
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
No reviews

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Stay near popular Chester attractions

Chester City Hall

7.8/10 (23 reviews)
Chester City Hall stands as the administrative heart of one of Pennsylvania's oldest cities. Visitors can explore its architecture and learn about local governance during regular business hours.
See properties

What to do in Chester

Philadelphia Haunted Halloween Tour: Terror Beyond the Walls

Philadelphia Haunted Halloween Tour: Terror Beyond the Walls

$65
per adult
Philadelphia Haunted Halloween Tour: Terror Beyond the Walls
LEGOLAND® Discovery Center Philadelphia

LEGOLAND® Discovery Center Philadelphia

$25
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Philadelphia
Polaris Slingshot Rental-Philadelphia, PA

Polaris Slingshot Rental-Philadelphia, PA

$250
per traveler
Polaris Slingshot Rental-Philadelphia, PA
See all activities in Chester

Chester Hotel Deals

Comfort Inn Philadelphia International Airport West

Comfort Inn Philadelphia International Airport West

3 out of 5
1300 Providence Ave Chester PA
Fully refundable
$84 nightly
The price is $93 total per night from Nov 9 to Nov 10
$93 total
Nov 9 - Nov 10
Total with taxes and fees
7/10 Good! (1,243 reviews)
"No complaints whatsoever ever"

Reviewed on Nov 2, 2026

Comfort Inn Philadelphia International Airport West
Club Quarters Hotel Rittenhouse Square, Philadelphia

Club Quarters Hotel Rittenhouse Square, Philadelphia

4 out of 5
1628 Chestnut St Philadelphia PA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Nov 29 to Nov 30
$115 total
Nov 29 - Nov 30
Total with taxes and fees
9/10 Wonderful! (4,871 reviews)
"Although the property is a bit dated, it is very clean."

Reviewed on Nov 2, 2026

Club Quarters Hotel Rittenhouse Square, Philadelphia
Doubletree by Hilton Philadelphia Airport

Doubletree by Hilton Philadelphia Airport

4 out of 5
4509 Island Ave Philadelphia PA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $113 total per night from Nov 24 to Nov 25
$113 total
Nov 24 - Nov 25
Total with taxes and fees
8.2/10 Very Good! (243 reviews)
"Honestly just slept here due to proximity to airport. Clean and well-maintained."

Reviewed on Nov 2, 2026

Doubletree by Hilton Philadelphia Airport
See all 3,131 properties in Chester
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.

Find the Best Chester Vacation Packages

Things to do near Chester

Chester, Pennsylvania, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can enjoy exciting tours, explore local shopping centers and malls, and partake in outdoor fun. With options for beach vacations and excellent adventures, Chester is an ideal destination for those seeking a lively city experience while also enjoying nature. Whether you're planning a family trip or a city-themed getaway, Chester has something for everyone.

Shopping

For a unique shopping experience, check out Sorella, just 5 miles from Chester, offering a variety of gifts. If you're up for a drive, the Reading Terminal Market and Chadds Ford Village & Barn Shops, both 13 miles away, provide a lively atmosphere with diverse shopping options.

Recreation

Experience the excitement at Lincoln Financial Field, just 11 miles away, for thrilling sports events. Enjoy skating adventures at Ice Works Skating Complex, 4 miles from Chester. For a cultural night out, visit the Mann Center for the Performing Arts, 12 miles away, featuring captivating performances for the whole family.

Adventure

Experience the thrill of motorsport at Bridgeport Speedway, a mere 3 miles from Chester, where high-speed racing creates an exhilarating atmosphere. For a nature-filled adventure, hike the Underground Railroad Trail, located 6 miles away, offering stunning scenery and outdoor exploration. Don't miss the Narberth Tennis Club, 12 miles away, for some active fun.

Nightlife

Chester's nightlife offers vibrant experiences, from lively bars to cozy lounges. Check out the Chester Waterfront for scenic views and a drink, or explore local favorites like the Blue Rose Restaurant for a relaxed vibe. Enjoy live music at venues that keep the energy high well into the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, Pennsylvania, is perfect for family outings and city-themed vacations, offering a mix of urban parks, charming neighborhoods, and modern college campuses. Visitors can explore local attractions such as the Chester Playhouse and delve into the city's rich history. Whether you're seeking cultural experiences or outdoor activities, Chester provides an engaging environment for everyone looking to enjoy a memorable getaway.

  • Wells Fargo Center: Experience thrilling sports and concerts at this vibrant arena, located 10 miles from Chester. With a lively atmosphere, it's a perfect spot for family entertainment and memorable events.
  • University of Pennsylvania: Explore the historic and modern campus of this prestigious institution, situated 11 miles away. The University offers a unique blend of academic excellence and urban energy, making it a fascinating place to visit.
  • Rittenhouse Square: Stroll through this picturesque neighborhood, located 12 miles from Chester. Rittenhouse Square is known for its beautiful park, upscale shops, and lively atmosphere, perfect for a relaxing afternoon in the city.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.3°F (0.7°C)Light RainMostly SunnySlightly LowSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
March43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighAverage
August76.1°F (24.5°C)Light RainMostly SunnyAverageAverage
September69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageSlightly High
November46.8°F (8.2°C)Light RainMostly SunnySlightly LowAverage
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Chester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Chester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Philadelphia Intl. Airport (PHL)
Population
34,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Philadelphia Museum of Art, Philadelphia Zoo and Mann Center for the Performing Arts

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Frequently asked questions

What types of vacation packages are available in Chester?
Chester, known for its family-friendly and urban attractions, offers several types of vacation packages:
  • Family-friendly package: A Chester vacation package can feature a stay at New Season Royals, rated 8.6 out of 10 by travelers, which offers kitchenettes and newly remodeled rooms, making it suitable for families.
  • Budget package: Nearly all hotels in Chester fall into the midrange tier. Comfort Inn Philadelphia International Airport West, rated 7.9 out of 10 by travelers, provides good value with free breakfast and is noted for its reasonable value.
  • Pet-friendly package: For those traveling with pets, options like Candlewood Suites Chester - Philadelphia International Airport by IHG, rated 7.9 out of 10 by travelers, welcome furry companions, with travelers frequently highlighting the amazing staff.
  • Packages with free breakfast: Comfort Inn Philadelphia International Airport West, rated 7.9 out of 10 by travelers, is praised for its free breakfast, helping travelers save on dining costs.
How can I save money on a Chester vacation package?
When you bundle, you can save up to 30%*. To save money on a Chester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does a Chester vacation package cost?
A Chester vacation package typically costs around $600 per adult for a weekend trip. Lower-priced bookings start from around $300 per adult, while other packages can reach up to $1,100 per adult.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Chester vacation package deals?
The cheapest Chester vacation package deals can be as low as around $310 per adult for weekend trips. Separately, June typically has the lowest average monthly price, around $550 per adult, for a 2-day trip, while March follows closely at around $580, for a 3-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — nearly all Chester packages include some savings versus booking separately, typically around $40 per adult. Week-long trips can save even more, often around $65 per adult. Browse cheap vacation packages in Chester on Expedia for current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Chester?
The peak months for a Chester vacation are typically May and June, when the city sees the highest demand from travelers. While June is a popular time, it also shows some of the lowest package prices, making it a potentially good value for a shorter trip.

For those seeking a quieter and generally more affordable experience, January, February, and March are the quietest months. January, in particular, tends to offer lower prices for a Chester vacation package.
What's included in a Chester vacation package?
A Chester vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in Chester offer free breakfast, and some hotels may also offer airport shuttle service to and from Newark Liberty Intl. Airport (EWR).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Chester?
For families, a Chester vacation package with a stay at New Season Royals, rated 8.6 out of 10 by travelers, is a great option. It offers kitchenettes and newly remodeled rooms, with travelers often praising its great facilities and better-than-expected location.

For travelers seeking value, Comfort Inn Philadelphia International Airport West, rated 7.9 out of 10 by travelers, is a strong choice. This hotel provides free breakfast and is noted by travelers for its excellent location and reasonable value.

Couples looking for a convenient stay could consider a package featuring Candlewood Suites Chester - Philadelphia International Airport by IHG, rated 7.9 out of 10 by travelers. It features kitchens and spacious rooms, with travelers frequently highlighting the amazing staff and convenient location.
Is Chester better suited for a beach vacation or a cultural trip?
A Chester vacation is primarily suited for cultural exploration and urban attractions, with a strong focus on family-friendly activities. The city boasts a rich history, evident in sites like the 1724 Chester Courthouse, the oldest public building in the United States, and St. Paul's Church, originally built in 1702, which holds historical significance including the burial site of a Declaration of Independence signer.

Chester offers a variety of city experiences, from catching a game at Subaru Park to shopping at the King of Prussia Mall. Your Chester vacation can be customized around these diverse activities.
What is the best time to book a Chester vacation package?
Book your Chester vacation package around 2 weeks before you travel. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 1 and 5 weeks out.

January, September, and October are the most popular months for Chester packages, so booking earlier is advisable if you're traveling during these months.
What are the top things to do in Chester?
A Chester vacation offers a range of activities, from sports and entertainment to shopping:

Browse and book things to do in Chester on Expedia.
How many days do you need for a Chester vacation?
Most Chester vacation packages are around 3 days, with most travelers choosing weekend trips. This duration allows you to experience key attractions like catching a game at Subaru Park, exploring the historic St. Paul's Church, or visiting the King of Prussia Mall.

Nearly a third of travelers opt for week-long trips, providing more time to delve deeper into the area's cultural offerings and family-friendly attractions, while a select few choose two-week trips for extended exploration.
Is Chester a good destination for a weekend vacation?
Chester is an excellent destination for a weekend vacation, with most travelers choosing weekend trips. In just a few days, you can enjoy the city's family-friendly attractions and cultural sites. Consider catching a game at Subaru Park or WSFS Bank Sportsplex, or exploring the historic Chester Courthouse.

A Chester vacation package can easily be tailored for a short, focused trip, allowing you to experience the highlights of this urban destination.
Do you need to rent a car in Chester, or is public transport enough?
For a Chester vacation package, public transport is generally sufficient for getting around the compact city center. Chester has an excellent public transport system, with SEPTA buses and Regional Rail serving the city, including the Chester Transit Center and Highland Avenue stations.

However, if your Chester vacation plans include exploring attractions further afield, such as the King of Prussia Mall about 8 miles away or Franklin Field about 19 miles away, a rental car can offer greater flexibility. This is especially true for Chester vacation packages with flights, as a car allows for easier access to destinations beyond the immediate city limits.
Are Chester vacation package hotels conveniently located?
Chester vacation package hotels are generally conveniently located, with many properties within easy walking distance of central Chester. For example, Candlewood Suites Chester - Philadelphia International Airport by IHG is about a 5-minute walk from central Chester, offering a convenient base.

New Season Royals is also well-situated, about a 10-minute walk from the city center, while Comfort Inn Philadelphia International Airport West is about a 15-minute walk away. These central locations make it easy to access local attractions and amenities during your stay.
Are there vacation package hotels in Chester within walking distance of restaurants and shops?
Many Chester vacation package hotels are within easy walking distance of restaurants and shops, particularly those located near the city center. For instance, Candlewood Suites Chester - Philadelphia International Airport by IHG is about a 5-minute walk from central Chester, placing you close to local dining and retail options.

New Season Royals is also conveniently located about a 10-minute walk from central Chester, and Comfort Inn Philadelphia International Airport West is about a 15-minute walk away. Choosing a hotel in this central area offers convenient access to the city's amenities.
Can I change or cancel my Chester vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chester vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chester?
To find last-minute vacation packages to Chester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chester vacation packages?
Free cancellation on a Chester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chester vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chester vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.