Chesterfield Vacations from $231

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Your Chesterfield Vacation

Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $404, price is now $231 per person
$231
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,474, price is now $823 per person
$823
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,030, price is now $688 per person
$688
per person
Apr 2 - Apr 4
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Beautiful property and room.

Reviewed on Jan 8, 2026

The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $820, price is now $556 per person
$556
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (243 reviews)
The staff are amazing! Love the amenities - the pool, recreation center, activities for the kids such as windchime arts and crafts. The arcade is always a hit. The Loft makes it so easy to not have to stress about a place to go to for dinner. The Cove is a great place for everyone!

Reviewed on Dec 28, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,196, price is now $820 per person
$820
per person
Mar 16 - Mar 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Amazing week - family stay for Christmas in town - thank you very much! We’ll be back!…….

Reviewed on Dec 28, 2025

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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

Chesterfield Hotel Deals

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
$106 nightly
The price is $118 total per night from Jan 21 to Jan 22
$118 total
Jan 21 - Jan 22
Total with taxes and fees
9.2/10 Wonderful! (2,262 reviews)
The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River.

Reviewed on Jan 6, 2026

D. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Feb 8 to Feb 9
$120 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (807 reviews)
I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights.

Reviewed on Jan 5, 2026

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN

Reviewed on Jan 4, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 494 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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
1,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Historic Northampton, Academy of Music Theater and Calvin Theatre and Performing Arts Center

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from $231 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?
November, December and January are the best times to search for cheap Chesterfield vacation packages. Opting to travel in less busy months means you can typically find better prices on accommodations and flights.
How many days is enough for Chesterfield?
With a well-organized travel plan, you can easily tick off the most popular Chesterfield attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, 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.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield break should be a relaxing escape from your busy life, not a source of money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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