Chester Vacations from $536

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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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $767, price is now $536 per person
$536
per person
May 28 - May 31
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (254 reviews)
Room was not easy to get to and it was 0 degrees out …1st they put me out in a building where the property was a sheet of ice so I asked to be moved to the main building since I was by myself. Fortunately, they moved me, but the room was confusing to get to. :-( The pool was closed for maintenance, and I was planning to swim. :-( The room was great, clean and a comfortable bed, so I would stay again, but I would request staying closer to the lobby next time.

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,520, price is now $914 per person
$914
per person
May 7 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
Price was $838, price is now $597 per person
$597
per person
May 27 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (3,136 reviews)
Very welcoming staff and beautiful lobby.

Reviewed on Mar 23, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $1,584, price is now $1,138 per person
$1,138
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,612 reviews)
Air conditioner was tricky! we never were able to get the desired temp out of it

Reviewed on Mar 23, 2026

Blue - Inn on The Beach

Blue - Inn on The Beach

3.5 out of 5
Save 100% on your flight
Price was $3,189, price is now $2,295 per person
$2,295
per person
May 27 - Jun 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (209 reviews)
Staff was super friendly, room was great, they fulfilled all my our (anniversary) requests with professionalism and without hesitation. Only downside was the TV in the living room and we couldnt watch it at bedtime. Other than that it was great! Thats why we keep coming back!

Reviewed on Mar 1, 2026

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Chester Hotel Deals

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St. Manchester NH
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (1,149 reviews)
Mold on the wall

Reviewed on Mar 23, 2026

DoubleTree by Hilton Manchester Downtown
DoubleTree by Hilton Boston - Andover

DoubleTree by Hilton Boston - Andover

4 out of 5
123 Old River Rd Andover MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Apr 3 to Apr 4
$118 total
Apr 3 - Apr 4
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
I was under the impression that the continental breakfast came with the room price, I was unpleasantly surprised when I had to pay $50 extra dollars for a breakfast I had already expected to have available to me with the price of the room. That really bothered me.

Reviewed on Mar 22, 2026

DoubleTree by Hilton Boston - Andover
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $80 total per night from Mar 24 to Mar 25
$80 total
Mar 24 - Mar 25
Total with taxes and fees
8.8/10 Excellent! (1,718 reviews)
The staff was friendly and thorough. The rooms were clean and the location was perfect for our visit to a Tuscan village event. The only complaint..if you call it that, would be the room was a bit dated and had some loose wallpaper and chipped corners on walls. Accessible outlets by the beds would ...

Reviewed on Mar 23, 2026

Park View Inn - Salem
See all 479 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

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
5,200
Top Sights
Canobie Lake Park, Bear Brook State Park and Zorvino Vineyards

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $536 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.