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.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $1,010, price is now $686 per person
$686
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $1,894, price is now $1,217 per person
$1,217
per person
Jun 24 - Jul 1
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
The Highliner Hotel

The Highliner Hotel

2 out of 5
Downtown Gloucester
Save 100% on your flight
Price was $1,538, price is now $1,008 per person
$1,008
per person
Jun 8 - Jun 12
found 10 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
This hotel features free WiFi in public areas, express check-out, and concierge services. A virtual front desk are provided for your convenience.
The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,693, price is now $1,155 per person
$1,155
per person
Jun 18 - Jun 20
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Limo/town car service, a lobby fireplace, and a hair salon are also on offer.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
Price was $1,862, price is now $1,299 per person
$1,299
per person
Jun 17 - Jun 22
found 10 hours ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
This luxury hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a 24-hour business center, and a coffee shop are also offered.

Top Chesterfield hotels deals

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
$150 nightly
The price is $168 total per night
$168 total
Apr 20 - Apr 21
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
May 17 - May 18
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.
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

2.5 out of 5
400 Russell St Hadley MA
Free Cancellation
$127 nightly
The price is $141 total per night
$141 total
May 5 - May 6
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.
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
$111 nightly
The price is $127 total per night
$127 total
May 10 - May 11
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.
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
$89 nightly
The price is $102 total per night
$102 total
May 3 - May 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.
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $146 total per night
$146 total
May 5 - May 6
Total with taxes and fees
This hotel 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
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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

Krug Sugarbush

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

Krug Sugarbush

Frequently asked questions

How much are vacation packages to Chesterfield?
With vacation packages available from just $686, 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