Chesterfield Vacations from $575

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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.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was $816, price is now $575 per person
$575
per person
May 22 - May 26
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8/10 Very Good! (259 reviews)
The staff were really nice and the food was good. They have an excellent location right on the beach.

Reviewed on Mar 12, 2026

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $1,259, price is now $807 per person
$807
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.4/10 Exceptional! (2,227 reviews)
Cute property! Super friendly staff.

Reviewed on Apr 10, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $4,229, price is now $2,764 per person
$2,764
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (248 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,068, price is now $1,454 per person
$1,454
per person
May 14 - May 17
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).

Reviewed on Apr 4, 2026

The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $1,196, price is now $847 per person
$847
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,092 reviews)
Great hotel and location. Rooms were a bit old but excellent location and condition.

Reviewed on Apr 9, 2026

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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 refundable
$150 nightly
The price is $168 total per night from Apr 14 to Apr 15
$168 total
Apr 14 - Apr 15
Total with taxes and fees
9.4/10 Exceptional! (2,243 reviews)
Cute property! Super friendly staff.

Reviewed on Apr 10, 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 May 10 to May 11
$120 total
May 10 - May 11
Total with taxes and fees
9/10 Wonderful! (900 reviews)
Yes everything was very geared for a enjoyable time.

Reviewed on Apr 11, 2026

Berkshire Mountain Lodge
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

2.5 out of 5
400 Russell St Hadley MA
Fully refundable
$127 nightly
The price is $141 total per night from Apr 20 to Apr 21
$141 total
Apr 20 - Apr 21
Total with taxes and fees
9.2/10 Wonderful! (1,017 reviews)
Great breakfast, waffles, etc. "K." said there was only one key, so I was a lil bit upset, but the next morning "J." Made all the difference very charming, and courteous young man. Location is perfect, but a bigger well lit, and visible Sign would be recommended.

Reviewed on Apr 10, 2026

Comfort Inn & Suites Hadley - Amherst
See all 515 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 $575 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.