Chesterfield Vacations from NT$38,451

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The Latest Chesterfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
per person
Sep 22 - Sep 25
found 6 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
Rooms are very small no place to sit inside the room

Reviewed on 2025/8/8

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 22 - Sep 25
found 6 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
9.6/10 Exceptional! (135 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 2025/8/5

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
per person
Sep 22 - Sep 25
found 6 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
9.2/10 Wonderful! (1,010 reviews)
Smells fantastic in this place. Perfect linens and room arrangement. It is a cut above the surrounding hotels.

Reviewed on 2025/8/7

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Sep 22 - Sep 25
found 6 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 2025/7/25

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
per person
Sep 22 - Sep 25
found 6 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
8.8/10 Excellent! (1,876 reviews)
Enjoyed the location and friendly staff!

Reviewed on 2025/8/8

Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is NT$2,758 per night from Aug 21 to Aug 22
NT$2,758
NT$3,156 total
Aug 21 - Aug 22
includes taxes & fees
7/10 Good! (1,000 reviews)
"Staff was very friendly. The price was right"

Reviewed on 2025/8/4

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on 2025/8/5

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Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is NT$3,852 per night from Aug 12 to Aug 13
NT$3,852
NT$4,475 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (2,242 reviews)
"Clean, comfortable beds and fun live music at the restaurant attached"

Reviewed on 2025/8/6

D. Hotel Suites & Spa
See all 461 properties in Chesterfield
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.

Discover the most popular places to visit in Chesterfield

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.

Chesterfield Gorge

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from NT$38,451 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organized travel plan, you can easily visit the top Chesterfield sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Chesterfield.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chesterfield. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the right Chesterfield vacation package for you.

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