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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $858, price is now $616 per person
$616
per person
Dec 22 - Dec 28
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the gym and free buffet breakfast each morning. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,324, price is now $761 per person
$761
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $1,690, price is now $1,031 per person
$1,031
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a sauna on site, and laundry facilities and concierge services are also offered.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,099, price is now $676 per person
$676
per person
Dec 25 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,030, price is now $1,390 per person
$1,390
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Top Chesterfield hotels deals

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
$83 nightly
The price is $95 total per night
$95 total
Nov 16 - Nov 17
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $127 total per night
$127 total
Nov 17 - Nov 18
Total with taxes and fees
This aparthotel 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
$125 nightly
The price is $139 total per night
$139 total
Oct 26 - Oct 27
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the gym and free buffet breakfast each morning. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Pool
Hot Tub
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
Get rates
This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, a snack bar/deli, and a lobby fireplace are also offered.
Breakfast included
Free WiFi
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
Free Cancellation
$101 nightly
The price is $116 total per night
$116 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.
Parking included
Free WiFi
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street West Springfield MA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $98 total per night
$98 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
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.

Stay near popular Chesterfield attractions

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.
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Frequently asked questions

How much are vacation packages to Chesterfield?
With vacation packages available from just $616, 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

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