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.
Cold Spring Resort

Cold Spring Resort

3.5 out of 5
per person
Aug. 1 - Aug. 4
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
9/10 Wonderful! (85 reviews)
A Top notch team and a remarkable property, Cold Spring Resort! Thank you to the amazing staff; General Manager Corinne, Manager Sharmine, Kim, Elin, Ann, Tom and housekeepers! I have a high work ethic delivering customer service excellence in my business career as a Realtor and managing luxury properties. I will inform you of this team delivering exceptional service on a consistent basis! I spoke to the entire team while I was researching the resort via the phone! My husband and I had an outstanding June 2024 vacation! The professional, personal and positive attitudes of the Cold Spring Resort team is sincerely appreciated! Cold Spring Resort is your vacation getaway with the impressive extreme cleanliness of the condominiums, calmness of nature, price point and the A team! Thank you everyone for working so hard! You have so much to be proud of!

Reviewed on Jun. 12, 2024

1st Floor Suite in the Heart of Concord

1st Floor Suite in the Heart of Concord

2 out of 5
per person
Aug. 1 - Aug. 4
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
No reviews
The Centennial

The Centennial

4 out of 5
per person
Aug. 1 - Aug. 4
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
8.8/10 Excellent! (767 reviews)
It was pretty and well kept.

Reviewed on May 27, 2024

Exeter Inn

Exeter Inn

3.5 out of 5
per person
Jul. 28 - Aug. 1
just found
Roundtrip flight included
Montreal (YUL) to Manchester (MHT)
8.8/10 Excellent! (842 reviews)
The room was very small The bed was almost blocking the entrance door The shower was tiny and water splashed all around outside.

Reviewed on Jun. 5, 2024

Independence Inn

Independence Inn

4 out of 5
per person
Aug. 1 - Aug. 4
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Manchester (MHT)
8.4/10 Very Good! (58 reviews)
I would rate this property, generally speaking, as average because some things could have been a little cleaner (ex. The bedroom rug needs to be cleaned.) I was a little disappointed when the in room coffee maker didn’t work.

Reviewed on Apr. 11, 2024

Chesterfield Hotel Deals

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 $121 per night from Jun. 23 to Jun. 24
CA $121
CA $133 total
includes taxes & fees
Jun 23 - Jun 24
6.8/10 (1,003 reviews)
"Everything so convenient"

Reviewed on Jun. 12, 2024

Colonial Motel And Spa
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
8.2/10 Very Good! (1,017 reviews)
"We enjoyed our stay. Older building with charm. Friendly staff"

Reviewed on Jun. 12, 2024

Get rates
The Covered Bridge Inn
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 $168 per night from Jun. 23 to Jun. 24
CA $168
CA $185 total
includes taxes & fees
Jun 23 - Jun 24
8.2/10 Very Good! (908 reviews)
Great stay
"Like other reviewers already stated - the hotel is excellent - super friendly staff, I stayed in. King bed room - the room was spacious, clean, comfortable mattress - not too soft, not too hard. Good breakfast choices. They do state at the front desk that pool/ hot tub are being renovated with no ..."

Reviewed on Jun. 10, 2024

Hampton Inn Brattleboro
See all 468 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.

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 $816, 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.