Chester Vacations from $456
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Your Chester Vacation
When a getaway to the city is calling, answer it with a Chester vacation package. With all your travel needs taken care of before you leave, all you need to do here is focus on making unforgettable memories. Fill your schedule with tours of Hacklebarney State Park, Alstede Farms and Schooleys Mountain County Park, some of the top attractions you just have to see during your trip to Chester. A few clicks is all it takes to build your perfect Chester vacation on Expedia.
The Latest Chester Vacation Packages
- Parkway House Goshen Family-Friendly Bed & Breakfast
Jan 15 - Jan 18Parkway House Goshen Family-Friendly Bed & Breakfast + Flight
Goshen3 nights3.0 star property9.8/10 - Exceptional (46 reviews)"What a amazing property the stuff are amazin"Reviewed November 1, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop$738$456found 1 day agoper traveler - JW Marriott Essex House New York
Jan 21 - Jan 25JW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,002 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - The St. Regis New York
Jan 26 - Jan 28The St. Regis New York + Flight
Manhattan2 nights5.0 star property9.2/10 - Wonderful (294 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$1,844$1,125found 1 day agoper traveler - 1 Hotel Central Park
Dec 30 - Jan 31 Hotel Central Park + Flight
Manhattan4 nights5.0 star property9.0/10 - Wonderful (1,003 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop EWR - ATL • Nonstop$2,610$1,596found 1 day agoper traveler - Park Lane New York
Jan 29 - Feb 2Park Lane New York + Flight
Manhattan4 nights5.0 star property8.4/10 - Very good (1,846 reviews)"The room had an unbelievable view of Central Park (as advertised and booked), but was otherwise mediocre. Staff was generally friendly and helpful, except for the person who checked us in - who, to be fair, looked exhausted."Reviewed November 3, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop$1,055$654found 1 day agoper traveler
Where to stay near Chester
Morristown
Discover Morristown, a vibrant destination perfect for families and weekend getaway seekers who will appreciate its blend of urban charm and outdoor adventure. Enjoy the cultural richness at the Mayo Performing Arts Center, explore the historic grounds of Drew University, or unwind at Morristown Green. Located about 11 miles by car from Chester, Morristown offers easy access to a variety of shopping and recreational activities, making it a smart choice for your next hotel booking.
Budd Lake
Experience the charm of Budd Lake, an excellent hub for families and outdoor enthusiasts who want to immerse themselves in nature and adventure. With attractions like the historic Waterloo Village, the scenic Allamuchy Mountain State Park, and the vibrant Centenary College nearby, Budd Lake offers a delightful blend of recreation and relaxation. Located about 8 miles by car from Chester, this area is a smart choice for your vacation stay, providing easy access to both fun and tranquility.
Flanders
If you are a family traveler, look no further than Flanders, which features a variety of attractions for all ages. Explore Alstede Farms for fresh produce and hands-on fun, or unwind at Mount Olive Dog Park for some outdoor activity with your furry friend. With a bustling shopping center and arena entertainment facility nearby, Flanders ensures a lively experience. Located about 4 miles by car from Chester, it’s a smart choice for your next getaway.
Mount Olive
Mount Olive stands out as a prime spot for families and outdoor enthusiasts interested in exploring its rich offerings. Here, visitors can enjoy activities at local landmarks like Centenary College, the scenic Waterloo Village, and the vibrant Alstede Farms. With a variety of shopping and recreational options, Mount Olive serves as a perfect base for those looking to unwind or embark on adventures. Located about 5 miles by car from Chester, Mount Olive is a smart choice for your next getaway.
Long Valley
Travelers visiting the area often choose Long Valley, especially families and nature enthusiasts, seeking close proximity to outdoor adventures and city experiences. With attractions like Alstede Farms, Hacklebarney State Park, and Centenary College, Long Valley offers a delightful blend of recreation and local charm. Located about 5 miles by car from Chester, this area makes for a convenient and appealing home base for your vacation, promising a memorable stay in a picturesque setting.
Discover the most popular places to visit in Chester
Chester Hotel Deals
"The continental breakfast is a great addition to the stay."
Extended Stay America Suites Mt Olive Budd Lake
Extended Stay America Suites Mt Olive Budd Lake
Holiday Inn Budd Lake - Rockaway Area by IHG
Holiday Inn Budd Lake - Rockaway Area by IHG"Breakfast was great. Clean room. Hotels was very clean"
Holiday Inn Express Hotel & Stes Mt. Arlington Rockaway Area by IHG
Holiday Inn Express Hotel & Stes Mt. Arlington Rockaway Area by IHG"The desk clerk was very considerate and gave me a room handicap accessible. The equipment in the bathroom, tub, toilet,sink very clean. Checked the bed and bedding very comfortable, I slept like a baby. The breakfast was ok here, But will recommend to friends and the handicap community as well."
"We enjoyed our stay very much at this quaint property. James was helpful and greeting us with a smile."
Find out more about Chester
Things to do in and around Chester
Chester, New Jersey, is perfect for family-friendly vacations and outdoor adventures. Visitors can enjoy a variety of activities, including shopping at local centers and exploring entertainment facilities. Outdoor games and day trips offer excellent opportunities for adventure, while Chester's vibrant atmosphere makes it an ideal spot for a beach vacation. Experience the charm of this quaint town and create lasting memories with family and friends.
Shopping
For great shopping in Chester, explore The Streets of Chester Shopping Center right in town, offering a variety of shops with a family-friendly vibe. If you're up for a drive, check out Roxbury Mall, 6 miles away, or Rockaway Townsquare, located 11 miles from Chester, both featuring diverse shopping options.
Recreation
Experience the enchanting performances at Pax Amicus Castle Theatre, just 6 miles from Chester, where culture and romance blend beautifully. Enjoy sports activities and events at Mennen Sports Arena, located 12 miles away. For relaxation, visit Hedden Park, 9 miles away, offering a serene atmosphere perfect for unwinding.
Adventure
Stryker Airsoft offers an exhilarating arcade adventure experience, perfect for families seeking excitement just 8 miles from Chester. For water fun, Tomahawk Lake Water Park features thrilling slides and attractions, located 15 miles away. The Funplex, another arcade adventure zone, promises family-friendly entertainment and is 17 miles from Chester.
Nightlife
Chester, New Jersey, offers a charming nightlife with cozy bars and local eateries. Enjoy craft brews at the Chester Depot or savor cocktails at the Black River Barn. For a laid-back vibe, unwind at the historic Red Mill, where you can enjoy live music and great company.
Find the best attractions in and around Chester
Chester, New Jersey, is perfect for family-friendly and outdoor vacations, offering a blend of urban parks, state parks, and nature reserves. Visitors can enjoy a variety of attractions that cater to outdoor enthusiasts and those seeking cultural and family experiences. Whether you're hiking in a state park or exploring local urban spaces, Chester's charm and diverse activities make it an ideal destination for all types of travelers.
- Alstede Farms: Experience the charm of rural life at Alstede Farms, where you can pick fresh fruits, enjoy seasonal festivals, and interact with farm animals. This family-friendly farm offers a variety of activities, making it an ideal spot for a fun-filled day.
- Hacklebarney State Park: Just 3 miles from Chester, Hacklebarney State Park is perfect for outdoor enthusiasts. Hike through scenic trails, explore beautiful waterfalls, and enjoy a picnic surrounded by nature. This park offers adventure and tranquility in a picturesque setting.
- Willowwood Arboretum: Located 4 miles from Chester, Willowwood Arboretum invites visitors to stroll through its diverse plant collections and beautifully landscaped gardens. Ideal for families, this serene space offers educational opportunities and a chance to connect with nature.
Best time to go to Chester
The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.
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 to Chester during the low season (January to March) for more affordable options.
- 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.
Frequently Asked Questions
What are the top things to do in Chester?
Chester, United States of America, is an outdoor and nature destination known for its family-friendly attractions. A Chester vacation offers a variety of activities:
Browse and book things to do in Chester on Expedia.
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.
Do you need to rent a car in Chester, or is public transport enough?
For a Chester vacation package, renting a car is highly recommended to fully explore this outdoor and nature destination. While Chester is known for family-friendly attractions, many points of interest are spread out, and a car offers the most flexibility to reach them. Public bus service in Chester was discontinued in June 2010, meaning there are no local bus routes available.
If you're flying into the area, you'll arrive at airports such as John F. Kennedy International Airport (JFK), Newark Liberty International Airport (EWR), LaGuardia Airport (LGA), Philadelphia International Airport (PHL), or Westchester County Airport (HPN), all of which require ground transportation to reach Chester. A rental car allows you to easily visit attractions like Alstede Farms or Hacklebarney State Park, making your Chester vacation packages with flights more convenient.
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.