Deals on vacations and trips to Chesterfield

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Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,176, price is now $747 per person
$747
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was $1,451, price is now $845 per person
$845
per person
Oct 1 - Oct 4
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,692, price is now $1,720 per person
$1,720
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop 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.
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $4,348, price is now $2,785 per person
$2,785
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Market Square Inn

Market Square Inn

2 out of 5
Downtown
Save 100% on your flight
Price was $11,753, price is now $7,618 per person
$7,618
per person
Oct 10 - Oct 17
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

Top Chesterfield hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night
$173 total
Aug 19 - Aug 20
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
$142 nightly
The price is $158 total per night
$158 total
Jul 26 - Jul 27
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.
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
$165 nightly
The price is $184 total per night
$184 total
Jul 27 - Jul 28
Total with taxes and fees
This historic hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace are also offered.
Parking included
Free WiFi
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
$94 nightly
The price is $108 total per night
$108 total
Aug 3 - Aug 4
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.
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
$144 nightly
The price is $161 total per night
$161 total
Aug 9 - Aug 10
Total with taxes and fees
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.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$145 nightly
The price is $162 total per night
$162 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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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.
See properties

Frequently asked questions

How much are vacation packages to Chesterfield?
With vacation packages available from just $747, 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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