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.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features an indoor pool and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A garden, a picnic area, and barbecue grills are also on offer.
Holly Tree Resort

Holly Tree Resort

3 out of 5
Save 100% on your flight
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.
Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

3.5 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 25
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the express check-in and WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free full breakfast each morning.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip non-stop 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.

Top Chesterfield hotels deals

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
Get rates
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
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
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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
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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
The Ellery

The Ellery

3.5 out of 5
259 Elm Street, Northampton, MA
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This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden, a lobby fireplace, and a picnic area are also on offer.
Breakfast included
Pet friendly
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
Get rates
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
Riverdale Inn

Riverdale Inn

2 out of 5
1500 Riverdale Street, On Route 5, West Springfield, MA
Free Cancellation
Reserve now, pay when you stay
Get rates
This motel 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.
Parking included
Free WiFi
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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 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

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

Frequently asked questions

How much are vacation packages to Chesterfield?
With vacation packages available from just $469, 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