Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Appreciated the free airport shuttle on demand

Reviewed on Jul. 9, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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
The price is CA $153 per night from Jul 15 to Jul 16
CA $153
CA $166 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Good walkable location to down town destinations"

Reviewed on Jul. 11, 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 refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 20 to Jul 21
CA $129
CA $140 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (790 reviews)
"The king suite is great"

Reviewed on Jul. 12, 2025

Even Hotels Manchester Airport by IHG
Best Western Plus Executive Court Inn & Conference Center
Best Western Plus Executive Court Inn & Conference Center
3 out of 5
13500 S Willow St, Manchester, NH
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jul 15 to Jul 16
CA $146
CA $158 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very Good! (1,206 reviews)
"We stayed for 1 night before a flight. Easy check in, it was comfortable and close to the airport. Also, my kids were comfortable and fell right to sleep. That’s a lot coming from them since they are all under 6 years old. I’d stay again if needed!"

Reviewed on Jul. 11, 2025

Best Western Plus Executive Court Inn & Conference Center
See all 450 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $705 on Expedia for your Chester escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
If you're hoping to score a cheap Chester vacation package, consider planning a trip in January, February and March. You'll usually find lower rates on airfares and hotels during these quieter months --- ideal for travellers wishing to save money.
How many days is enough for Chester?
The ideal duration of your Chester vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to visit all the major sights and discover some hidden spots along the way.
How to find the best Chester package deals?
Use Expedia's filters to find some of the best Chester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Chester package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
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, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally 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 favourite type of stay, airline and car class.
When to book a vacation package to Chester?
Secure amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Chester trip.
How to plan a trip to Chester?

  1. Pick your dates: The things you'd like to do in Chester and your favourite season will help you decide when to go.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Chester. Then, choose a hotel that suits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Decide how many days away: Start by listing all the attractions and activities you'd like to experience in Chester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Chester vacation package.

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