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.
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,304, price is now $890 per person
$890
per person
Aug 20 - Aug 23
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
A coffee shop, free WiFi in public areas, and a snack bar/deli are available at this hostel. Express check-in is also provided.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,382, price is now $1,282 per person
$1,282
per person
Aug 18 - Aug 22
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.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was $3,104, price is now $2,020 per person
$2,020
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $2,395, price is now $1,594 per person
$1,594
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,354, price is now $911 per person
$911
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

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
$149 nightly
The price is $166 total per night
$166 total
Jul 5 - Jul 6
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
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Free Cancellation
$93 nightly
The price is $106 total per night
$106 total
Jun 24 - Jun 25
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
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
Free Cancellation
$130 nightly
The price is $145 total per night
$145 total
Jun 28 - Jun 29
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.
Breakfast included
Free WiFi
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
$119 nightly
The price is $133 total per night
$133 total
Jun 16 - Jun 17
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 & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
Free Cancellation
$122 nightly
The price is $136 total per night
$136 total
Jun 30 - Jul 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Jun 22 - Jun 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a terrace are also on offer.
Pool
Breakfast 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

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

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 $890, 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