
Chesterfield Vacation Packages
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Your Chesterfield Vacation
When a city escape is calling, answer it with a vacation package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of Spofford Lake, Asbury United Methodist Church and Madame Sherris Castle Ruins, some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield vacation is just a few clicks away with Expedia.
Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Exeter Inn
Price was CA $552, price is now CA $527 per person
CA $527
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
9/10 Wonderful! (1,008 reviews)
Such a charming and convenient location! Had a cozy little room, and enjoyed meals on the patio and reading in the lobby. Staff was so kind and happy to help. Would definitely come back!
Reviewed on Aug. 16, 2025


Holiday Inn Express Durham by IHG
Price was CA $682, price is now CA $672 per person
CA $672
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
8.6/10 Excellent! (866 reviews)
super new apartment, very clean, excellent shower, good breakfast, would come back for a weekend.
Reviewed on Aug. 12, 2025
Chesterfield Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 27 to Aug 28
CA $173
CA $188 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (880 reviews)
"Nice stay. Good value"
Reviewed on Aug. 18, 2025

Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Aug 21 to Aug 22
CA $194
CA $214 total
Aug 21 - Aug 22
includes taxes & fees
6.6/10 (1,006 reviews)
"Staff was helpful. Quiet area"
Reviewed on Aug. 17, 2025

Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
The price is CA $170 per night from Sep 2 to Sep 3
CA $170
CA $187 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very Good! (866 reviews)
"Great beach and nice rooms Breakfast can improve and pool is small"
Reviewed on Aug. 17, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.