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

Exeter Inn

3.5 out of 5
per person
Jul. 8 - Jul. 12
Roundtrip flight included
Montreal (YUL) to Manchester (MHT)
8.8/10 Excellent! (832 reviews)
Was a wonderful place to relax and enjoy the peaceful atmosphere. I will return one day and definitely stay again

Reviewed on Apr. 19, 2024

Chesterfield Hotel Deals

The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Apr. 28 to Apr. 29
CA $100
CA $112 total
includes taxes & fees
Apr 28 - Apr 29
8.2/10 Very Good! (1,000 reviews)
"Beds were squeaky but rooms are big"

Reviewed on Apr. 19, 2024

The Covered Bridge Inn
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Apr. 27 to Apr. 28
CA $170
CA $187 total
includes taxes & fees
Apr 27 - Apr 28
6.8/10 (1,000 reviews)
"Very comfortable"

Reviewed on Apr. 21, 2024

Colonial Motel And Spa
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Apr. 29 to Apr. 30
CA $154
CA $169 total
includes taxes & fees
Apr 29 - Apr 30
8.2/10 Very Good! (893 reviews)
"Good stay"

Reviewed on Apr. 13, 2024

Hampton Inn Brattleboro
See all 473 properties in Chesterfield
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Our Chesterfield packages, which start from just CA $1,038, are the perfect way to save precious money. Choose your favorite hotels, flights and more to create a custom-built escape.
How do I get a cheap travel package to Chesterfield?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we’ve got them all. Choose the combination that best suits you and see your savings pile up. We know a package deal is never one-size-fits-all. That’s why we offer more than 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Chesterfield vacation.
Where should I stay in Chesterfield?
With interesting attractions like Spofford Lake and Madame Sherri Forest in this area, see if you can find a hotel near either one. Asbury United Methodist Church is another sight in Chesterfield that lures the crowds.
How far in advance should I book my Chesterfield vacation?
It depends on the air carrier, but you can generally look up international airfares on Expedia nearly a year in advance. While it’s generally recommended to book ahead of time, lucky travelers occasionally find a cheaper ticket just weeks prior to departure dates.
What does an Expedia Chesterfield travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to create your perfect Chesterfield travel package. Once you’ve made your booking, you can add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the greater the savings!
What should I know before booking a Chesterfield travel package?
Whether it’s relaxation or adventure you’re after, a Chesterfield vacation package lets you organize your escape your way. Plus, you’ll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Chesterfield Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you certainly can. Just pick the airline you want and craft your ideal Chesterfield trip.
If I'm not able to travel, can I cancel my Chesterfield vacation package?
We get that the universe can throw the odd curveball. If you’ve booked a Chesterfield vacation package and have to amend or cancel it, we’re here to help. It’s always worth looking up our Customer Service Portal first for information. But generally, if you’ve taken out your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it’s more than 24 hours, your airline, hotel or car rental company may impose a fee.

Discover the most popular places to visit in Chesterfield

Image for Asbury United Methodist Church

Asbury United Methodist Church

You can learn about the history of Chesterfield with a trip to Asbury United Methodist Church. Amble around the area's riverfront, or seek out its ski slopes.

Asbury United Methodist Church
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.