Chester Vacations from $494

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Your Chester Vacation

With plenty of highlights as well as some hidden gems, this city is best explored with a Chester vacation package. Find a place to stay in Downtown Manchester, which is great for cafes, history and bars and pubs. There's plenty to see and do during your trip to Chester, including Zorvino Vineyards and Robert Frost Farm State Historic Site. No matter your travel plans or the size of your budget, organizing your ultimate tailored Chester vacation is a cinch with Expedia.

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A wooden cabin interior with a window overlooking a snowy landscape, a wooden table with books and a mug, and a chair.
    Dec 9 - Dec 14

    Stonybrook Motel & Lodge + Flight

    Franconia
    4 nights
    2.0 star property
    7.6/10 - Good (1,001 reviews)
    Roundtrip • Los Angeles (LAX) - Manchester (MHT)
    LAX - MHT • 1 stop MHT - LAX • 1 stop
    $704
    $494
    per traveler
    found 18 hours ago
    Stonybrook Motel & Lodge
  • A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for four.
    Dec 21 - Dec 26

    Boston Lodge and Suites + Flight

    Dorchester
    5 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • Nonstop
    $1,565
    $769
    per traveler
    found 13 hours ago
    Boston Lodge and Suites
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 25 - Jan 29

    Boston Harbor Hotel + Flight

    North End
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $1,994
    $1,147
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.
    Jan 15 - Jan 18

    Iris Hotel Cape Cod + Flight

    Falmouth
    3 nights
    3.0 star property
    8.4/10 - Very good (437 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $847
    $501
    per traveler
    found 22 hours ago
    Iris Hotel Cape Cod
  • A hotel with a well-maintained garden, a central fire feature, and a sign reading "Sea Crest".
    Jan 15 - Jan 18

    Sea Crest Beach Resort + Flight

    North Falmouth
    3 nights
    3.5 star property
    7.6/10 - Good (550 reviews)
    Roundtrip • Miami (MIA) - Boston (BOS)
    MIA - BOS • Nonstop BOS - MIA • Nonstop
    $710
    $503
    per traveler
    found 23 hours ago
    Sea Crest Beach Resort

Where to stay near Chester

Chester, New Hampshire, offers a delightful blend of outdoor adventures and romantic getaways. Explore the scenic beauty near Chester or venture to nearby cities, where family-friendly atmospheres and art await. Rest easy at hotels in close proximity for the perfect base to experience everything north Chester has to offer.
A cityscape with historic brick buildings, a river, and modern high-rises.

Manchester

For travelers seeking a vibrant getaway, Manchester, New Hampshire, offers an exciting blend of outdoor activities and entertainment. With attractions like the modern Southern New Hampshire University and the historic Saint Anselm College, visitors can enjoy both education and culture. Additionally, the Center of New Hampshire Expo Center hosts various events throughout the year. Located about 13 miles by car from Chester, Manchester serves as an excellent base for exploring the region's diverse experiences, making it a smart choice for your stay.

A river with a bridge, trees, and a park with benches.

Salem

Plan your stay in Salem, New Hampshire, a top-rated choice for families and outdoor enthusiasts looking for a mix of adventure and relaxation. With attractions like the arcade adventure zone and nearby beaches, Salem offers a fun-filled experience for all ages. Located about 13 miles by car from Chester, it's a perfect launching point for exploring local landmarks like America’s Stonehenge and the Atkinson Country Golf Course. Choosing Salem for your vacation ensures a memorable getaway.

A town with a central street, buildings, and a forested hill in the background.

Derry

Make your vacation planning effortless by staying in Derry, a haven for outdoor enthusiasts and families thanks to its abundance of activities. Visitors will enjoy attractions like the Robert Frost Farm State Historic Site and Pearson Memorial Park, perfect for weekend getaways or romantic outings. With its close proximity to a beautiful lake and family beach, Derry offers a delightful experience year-round. Located about 6 miles from Chester, Derry is a smart choice for your stay.

A frozen river with sunlight reflecting on the ice, surrounded by trees and a cloudy sky.
Photo by Brittney Geary
Open Photo by Brittney Geary

Sandown

Immerse yourself in Sandown, where families and nature enthusiasts can easily access a variety of outdoor adventures and scenic spots. This charming city offers delightful experiences, from the intriguing America's Stonehenge to the tranquil family beach and the vibrant arcade adventure zone, perfect for weekend getaways. Located about 4 miles from Chester, Sandown is a smart choice for travelers seeking a mix of relaxation and excitement amid beautiful landscapes.

A lake with lily pads and reeds, surrounded by dense forest and a cloudy sky.

Auburn

Travelers visiting the area often choose Auburn, especially families and outdoor enthusiasts seeking close proximity to scenic spots. With attractions like Lake Massabesic for a day of relaxation and adventure, and educational venues such as Southern New Hampshire University and Saint Anselm College, there's something for everyone. Auburn is about 6 miles from Chester, making it an easy escape for a weekend getaway. It's a smart choice for those looking to enjoy a blend of nature and culture during their stay.

Discover the most popular places to visit in Chester

Chester Town Hall

After visiting Chester Town Hall, make a plan to see the other sights and activities in Chester.
See properties

Chester Hotel Deals

A modern lobby with a staircase, a seating area, and a glass door entrance.

Garner Hotel Londonderry - Manchester by IHG

Garner Hotel Londonderry - Manchester by IHG
2.5 star property
6.5 mi from Chester
8.6 out of 10, Excellent, (1,006 reviews)
$95 nightly
The price is $103
Dec 3 - Dec 4
Total with taxes and fees
Garner Hotel Londonderry - Manchester by IHG
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.
See all properties in Chester

Frequently Asked Questions

How much does a Chester vacation package cost?

You'll find cheap prices from $494 on Expedia for your Chester escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.

What are the cheapest months to go to Chester?

If you're looking to score a cheap Chester vacation package, consider visiting in October, November and December. You'll typically find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.

How many days is enough for Chester?

Generally, a handful of days is enough to check out the top sights during your Chester vacation. But if you prefer to have more time to unwind or take day trips, think about extending your itinerary.

How to find the best Chester package deals?

Use Expedia's filter tool to help you find some great Chester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Chester package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book a Chester vacation as a package?

Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Chester vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Chester?

If you've got your Chester vacation dates locked in, book as soon as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.

Does Expedia offer Book Now, Pay Later Chester vacation packages?

Your Chester trip should be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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