Chesterfield Vacations from $178

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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.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $300, price is now $178 per person
$178
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
18/10 Exceptional! (2,226 reviews)
I love this hotel. The rooms are immaculately clean, the staff is great, and the communal bathrooms are always spotless. If you are OK with not having a bathroom in your room, this is an ideal spot -- great neighborhood, awesome restaurant and bar on site, and a really fun/cool vibe. I've stayed here three times so far and am looking forward to my next return trip.

Reviewed on Nov 14, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,135, price is now $457 per person
$457
per person
Jan 8 - Jan 12
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $428, price is now $249 per person
$249
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Great part of town, close to everything. Great stay!

Reviewed on Nov 13, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Save 100% on your flight
Price was $373, price is now $220 per person
$220
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
16.4/10 Exceptional! (1,946 reviews)
The room was a bit dirty specifically in the bathroom.

Reviewed on Nov 14, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
Price was $511, price is now $304 per person
$304
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.6/10 Exceptional! (1,001 reviews)
Pros: Clean throughout. Pool was clean and heated well. Staff is attentive and accommodating. King rooms are spacious. Nice views from the river side of the building. Bar has a great vibe to it. Food was excellent but a limited menu. Cons: Not a lot of activities in its proximity.

Reviewed on Nov 14, 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

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
$84 nightly
The price is $96 total per night from Nov 28 to Nov 29
$96 total
Nov 28 - Nov 29
Total with taxes and fees
7/10 Good! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.

Reviewed on Nov 7, 2025

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
$115 nightly
The price is $128 total per night from Dec 14 to Dec 15
$128 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.

Reviewed on Nov 4, 2025

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$134 nightly
The price is $150 total per night from Nov 16 to Nov 17
$150 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (2,247 reviews)
Very clean room, great variety of food at breakfast, friendly and helpful staff.

Reviewed on Nov 9, 2025

D. Hotel Suites & Spa
See all 482 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 $178 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.