Deals on vacations and trips to Chesterfield

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Chesterfield flight + hotel vacation packages

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

Marriott Boston Quincy

3.5 out of 5
Save 100% on your flight
Price was $522, price is now $323 per person
$323
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
Price was $636, price is now $354 per person
$354
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $607, price is now $371 per person
$371
per person
Jan 8 - Jan 13
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This aparthotel features laundry facilities. Take advantage of the self parking.
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,074, price is now $657 per person
$657
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This aparthotel features laundry facilities.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was $634, price is now $390 per person
$390
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.

Top Chesterfield hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $135 total per night
$135 total
Nov 30 - Dec 1
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
$134 nightly
The price is $150 total per night
$150 total
Nov 23 - Nov 24
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.
Pool
Hot Tub
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $97 total per night
$97 total
Dec 14 - Dec 15
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $99 total per night
$99 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
400 Russell St Hadley MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $141 total per night
$141 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $100 total per night
$100 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
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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.

Popular places to visit

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 Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.

Chesterfield Public Library

Chesterfield Gorge Reservation

You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.

Chesterfield Gorge Reservation

Frequently asked questions

How much are vacation packages to Chesterfield?
With vacation packages available from just $323, you won't need to empty your piggy bank to visit Chesterfield. Travelocity is here to help. Combine flights, hotels and tours into a package and score impressive discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Chesterfield?
Book your dream vacation with Travelocity. With access to 400 airlines and a massive 1,000,000 properties across the globe, creating the perfect Chesterfield package deal couldn't be simpler.
Why should I book my Chesterfield vacation bundle with Travelocity?
From our 24/7 support to our range of fantastic destinations, we're committed to fulfilling your vacation dreams. All you'll have to do is click and book — our Price Match Guarantee will ensure you lock in the cheapest price.
Can I save on my Chesterfield car rental if I bundle it with a hotel or flight?
With a Chesterfield vacation package, you can bundle your hotel, flight and car bookings and save a nice amount. If you'd love to explore the best of this fantastic destination, why not start with Fenway Park? This popular sight is 90 mi from Chesterfield. With a rental car, you'll be there in a jiffy.
Which airport is best for Chesterfield?
For plenty of visitors, a stay in Chesterfield means passing through Bradley Intl. Airport (BDL). This buzzing airport is located 35 mi south of the downtown area. You could also jet into Albany Intl. Airport (ALB) (55 mi away from central Chesterfield) or Hartford, CT (HFD-Hartford - Brainard) (45 mi away from central Chesterfield).
Where should I stay when visiting Chesterfield?
Many travelers choose to hit the hay at the Elegant Wilderness Cabin 12 Miles From Northampton. It's an excellent base for your Chesterfield getaway.

Photos of local treasures

Browse Chesterfield vacation photos for more inspiration