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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $1,378, price is now CA $950 per person
CA $950
per person
Aug 14 - Aug 16
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (5 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,267, price is now CA $2,095 per person
CA $2,095
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $11,082, price is now CA $7,467 per person
CA $7,467
per person
Aug 4 - Aug 11
found 5 hours ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,154, price is now CA $2,177 per person
CA $2,177
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Simply excellent in all aspects.

Reviewed on Jul 2, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,736, price is now CA $1,948 per person
CA $1,948
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 12 to Jul 13
CA $135
CA $147 total
Jul 12 - Jul 13
includes taxes & fees
8.4/10 Very good! (1,262 reviews)
"Overnight stay. Friendly staff. Breakfast was okay . The room was spacious. The only thing would be that there was a moldy smell in the room and that was due to the carpet. If they remove the carpet the room is perfect !"

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Salem NH
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd Andover MA
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Jul 5 to Jul 6
CA $165
CA $184 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very good! (2,081 reviews)
"The property appears clean and well maintained. The receptionist, Chad, was especially helpful when we requested a room change after being assigned a room with a smaller bed due to an automatic system allocation. He understood our concern and promptly arranged a replacement room for us."

Reviewed on Jul 3, 2026

La Quinta Inn & Suites by Wyndham Boston-Andover
Comfort Inn Manchester Airport

Comfort Inn Manchester Airport

2.5 out of 5
298 Queen City Ave Manchester NH
Fully refundable
The price is CA $146 per night from Jul 12 to Jul 13
CA $146
CA $158 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"Room was comfortable and our view of the mountains was amazing. Would stay here again."

Reviewed on Jul 2, 2026

Comfort Inn Manchester Airport
See all 496 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

Stay near popular Chester attractions

Chester Town Hall

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

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $950 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.

Explore a world of travel with Expedia

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