Chester Vacations from $340

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $836, price is now $340 per person
$340
per person
Dec 6 - Dec 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
Price was $730, price is now $445 per person
$445
per person
Dec 7 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (2,106 reviews)
Very poor A/C. Could not cool to appropriate temp.

Reviewed on Sep 26, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $567, price is now $356 per person
$356
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (479 reviews)
Great stay, friendly and accommodating staff

Reviewed on Sep 25, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Save 100% on your flight
Price was $856, price is now $563 per person
$563
per person
Dec 7 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
7.4/10 Good! (92 reviews)
great location and easy to access. cute /quant building and street. good amenities. would have liked a safe and more towels.

Reviewed on Sep 11, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Save 100% on your flight
Price was $586, price is now $390 per person
$390
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.2/10 Wonderful! (61 reviews)
Appears to be a brand new facility. Several area's are blocked off. Free breakfast is muffins and coffee.

Reviewed on Sep 26, 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
$131 nightly
The price is $142 total per night from Oct 12 to Oct 13
$142 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,022 reviews)
Recommend
"Excellent service by front desk,good room service and excellent breakfast"

Reviewed on Sep 18, 2025

DoubleTree by Hilton Manchester Downtown
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway, Salem, NH
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $101 total per night from Oct 5 to Oct 6
$101 total
Oct 5 - Oct 6
Total with taxes and fees
8.6/10 Excellent! (1,524 reviews)
"Always a great stay, central, affordable, and consistent experience"

Reviewed on Sep 26, 2025

Park View Inn - Salem
EVEN Hotels Manchester Airport by IHG

EVEN Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
$122 nightly
The price is $132 total per night from Sep 29 to Sep 30
$132 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (948 reviews)
"Room was clean"

Reviewed on Sep 25, 2025

EVEN Hotels Manchester Airport by IHG
See all 458 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 $340 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.