Chester Vacations from $279

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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.
Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
per person
Oct 15 - Oct 18
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (301 reviews)
Our family really enjoyed our stay at Parker Beach Lodge. It is a great location across from the beach, clean and staff was very friendly.

Reviewed on Aug 6, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
per person
Oct 15 - Oct 18
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (155 reviews)
This place is a majestic spot on the Cape within itself. We could stay on the premise and feel fulfilled with its beauty. The owners are awesome and it is just so perfect.

Reviewed on Aug 4, 2025

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Downtown Manchester
Save 100% on your flight
per person
Oct 17 - Oct 22
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,003 reviews)
We had car trouble. Had to book a hotel. We were tired and pretty miserable. Had one of the best nights sleep at any hotel ever. There was a tattoo convention at the convention center attached to the hotel. You couldn’t hear anyone in the other rooms. Highly recommend if you want a good night sleep

Reviewed on Aug 7, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug 5, 2025

InnSeason Resorts Surfside

InnSeason Resorts Surfside

3 out of 5
Save 100% on your flight
per person
Oct 15 - Oct 18
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (348 reviews)
The pool was great. Kids loved the playground. Loved the fire pit at night. Seating area outside our room was awesome. Being that close to the beach was amazing. Grounds are kept in very good condition. Absolutely loved our stay.

Reviewed on Jul 28, 2025

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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
$107 nightly
The price is $116 total per night from Aug 10 to Aug 11
$116 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,002 reviews)
"."

Reviewed on Aug 5, 2025

DoubleTree by Hilton Manchester Downtown
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Fully refundable
$122 nightly
The price is $132 total per night from Aug 10 to Aug 11
$132 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (853 reviews)
"Very nice and new and clean! Great pool!"

Reviewed on Aug 5, 2025

Even Hotels Manchester Airport by IHG
Seabrook Inn

Seabrook Inn

2.5 out of 5
9 Stard Rd, Seabrook, NH
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $107 total per night from Sep 1 to Sep 2
$107 total
Sep 1 - Sep 2
Total includes taxes and fees
6.4/10 (1,006 reviews)
clean room
"One night stay, clean room, ez check in and out"

Reviewed on Jul 28, 2025

Seabrook Inn
See all 456 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.

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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from $279 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.