Chester Vacations from ￥336,758

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥441,481, price is now ￥336,758 per person
￥336,758
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.8/10 Excellent! (1,524 reviews)
It was a great experience and very friendly staff!

Reviewed on Jul 11, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥645,939, price is now ￥450,924 per person
￥450,924
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was ￥446,286, price is now ￥344,474 per person
￥344,474
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥449,012, price is now ￥365,012 per person
￥365,012
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.6/10 Exceptional! (1,578 reviews)
Room was incredibly dated, especially the bathroom. Rug was frayed and there was an old school corded phone next to the toilet. Not what I expected from a “luxury” hotel. Soap, shampoo and conditioner were in tacky plastic white containers that had visible residue where they get filled. Bed was really comfy and staff was helpful, but the room needs some refreshing.

Reviewed on Jul 11, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥499,972, price is now ￥407,162 per person
￥407,162
per person
Aug 19 - Aug 24
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9/10 Wonderful! (1,254 reviews)
Beautiful hotel. Bathroom was great. Bathrobes were nice. Beds were comfy. Stayed in 4th floor gold. Very nice breakfast on this level. Didn’t go to main level restaurant / bar but looked great. Would definitely stay here again.

Reviewed on Jul 11, 2026

Find the Best Chester Vacation Packages

Chester Hotel Deals

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 ￥18,771 per night from Jul 19 to Jul 20
￥18,771
￥20,968 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very Good! (2,104 reviews)
".."

Reviewed on Jul 11, 2026

La Quinta Inn & Suites by Wyndham Boston-Andover
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 ￥16,166 per night from Jul 19 to Jul 20
￥16,166
￥17,540 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very Good! (1,406 reviews)
"Lobby entrance stairs looked like something from a movie or really upscale hotel! Everything was great except the 2nd floor hallway which had a slight stale cigarette smell and the carpet was quite frayed at the turn in the hall which could make a tripping hazard."

Reviewed on Jul 11, 2026

Best Western Plus Executive Court Inn & Conference Center
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 ￥16,354 per night from Aug 2 to Aug 3
￥16,354
￥17,744 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very Good! (1,277 reviews)
"Our room was close to the elevator -room 210, and unfortunately we heard the elevator a lot in the early morning. That was our only complaint-everything else was great!"

Reviewed on Jul 12, 2026

La Quinta Inn & Suites by Wyndham Salem NH
See all 481 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.

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 ￥336,758 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?
The ideal duration of your Chester vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the major sights and discover some hidden treasures along the way.
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.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Chester.
  2. Set a budget: Consider expenses like flights, transportation and food when working out how much to save for your trip to Chester. Then, pick a hotel that matches your budget, whether that's an affordable stay or a deluxe getaway.
  3. Determine how many days away: Start by making a list of all the sights and activities you want to get to in Chester. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your dates and duration, lock in the right Chester vacation package for you.

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.