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.
The Centennial
Price was CA $1,330, price is now CA $1,074 per person
CA $1,074
per person
Jul 24 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.
Reviewed on Apr 6, 2026
The Inn at Thorn Hill & Spa
Price was CA $1,660, price is now CA $1,325 per person
CA $1,325
per person
Jul 24 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
9.8/10 Exceptional! (1,000 reviews)
Beautiful Inn! Had a wonderful stay! The staff go above and beyond! Everyone was just so pleasant, friendly and very accommating
Reviewed on May 10, 2026
The Lake Estate on Winnisquam
Price was CA $1,974, price is now CA $1,584 per person
CA $1,584
per person
Jul 24 - Jul 28
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
9.6/10 Exceptional! (15 reviews)
Exceptional place beautiful landscape and very relaxing
Reviewed on May 10, 2026
Cold Spring Plymouth Resort
Price was CA $1,376, price is now CA $1,147 per person
CA $1,147
per person
Jul 25 - Jul 29
found 3 hours ago
Roundtrip flight included
Halifax (YHZ) to Manchester (MHT)
9.2/10 Wonderful! (209 reviews)
The property is good for skying in the area. Nothing fancy, but works perfectly for families who are out all day.
Reviewed on Apr 19, 2026
Chesterfield Hotel Deals
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jun 7 to Jun 8
CA $173
CA $191 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (973 reviews)
Great experience
Reviewed on May 8, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from May 13 to May 14
CA $211
CA $229 total
May 13 - May 14
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Not a pleasant experience! We had a water leak in our room, no hot water the second morning, and someone was in our room snd left a comforter on our bed! BUT, the front desk staff said they couldn’t see anything wrong…they couldn’t understand why we were so upset about it…someone had entered our ...
Reviewed on May 12, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from May 19 to May 20
CA $180
CA $198 total
May 19 - May 20
includes taxes & fees
8.6/10 Excellent! (879 reviews)
Everything was as it is described. Restful night sleep.
Reviewed on May 12, 2026
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.
