
Chesterfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.8/10 Excellent! (967 reviews)
The property was more attractive than most chain hotels. It was quite easy to find. The room was attractive and bed was comfortable. Breakfast was basic and not well stocked—one apple, one orange, and one carafe of coffee. The decaf had not been refilled. There were no plates or trays on which to put food and coffee, so it was hard to take coffee, fruit, toast etc. to the table. The bagels, jam, and yoghurt were good. That said, I would probably go there again when I need lodging in Concord.
Reviewed on Aug. 5, 2025

Hampton Inn by Hilton Concord/Bow
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.4/10 Very Good! (1,000 reviews)
The only thing was that the shower had mildew very visibly growing in it at the bottom. Everything else was fine.
Reviewed on Aug. 4, 2025


Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
9.4/10 Exceptional! (1,000 reviews)
The staff here was very friendly and the location convenient for access to BNH Pavillion show. Everything is clean and what one would expect of a Holiday Inn Express - a solid if unspectacular option...
Reviewed on Aug. 4, 2025
Chesterfield Hotel Deals

Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Aug 10 to Aug 11
CA $193
CA $212 total
Aug 10 - Aug 11
includes taxes & fees
6.6/10 (1,000 reviews)
"Always a pleasure to stay at the Colonial"
Reviewed on Jul. 28, 2025

Hampton Inn Brattleboro
1378 Putney Road, Brattleboro, VT
The price is CA $167 per night from Sep 4 to Sep 5
CA $167
CA $184 total
Sep 4 - Sep 5
includes taxes & fees
8/10 Very Good! (858 reviews)
"this is a very nice hotel, and we have stayed before and will stay again, but we will never stay in 212 again, they play music in the lobby and halls 24/7 which is fine, but 212 is right over the lobby and you can hear the drumming all night, it is very irritating, but like I said we have stayed ..."
Reviewed on Aug. 4, 2025

Keene Elm City Hotel, Ascend Hotel Collection
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Aug 12 to Aug 13
CA $172
CA $187 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very Good! (865 reviews)
"So happy we found this hotel. Our second stay in 3 weeks. Great location, very comfortable and clean. Staff is wonderful."
Reviewed on Aug. 2, 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.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.