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.
Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was CA $961, price is now CA $740 per person
CA $740
per person
Oct 18 - Oct 24
found 21 hours ago
Roundtrip flight included
Vancouver (YVR) to Manchester (MHT)
9/10 Wonderful! (173 reviews)
Beds were great, everything is new. Kitchenette is convenient. Convenience store right next door. I messaged that stairs are a problem and they called and emailed that we would be on the first floor. Not much room in the bathroom, only sink is part of kitchenette, but there is counter space for toiletries there.

Reviewed on Aug. 11, 2025

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was CA $1,752, price is now CA $1,402 per person
CA $1,402
per person
Oct 17 - Oct 24
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
7/10 Good! (1,002 reviews)
Large rooms. Comfortable bed. Pool. Light breakfast. Quiet. Easy parking. Receptive staff.

Reviewed on Aug. 25, 2025

Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was CA $1,021, price is now CA $866 per person
CA $866
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
Clean, friendly staff,

Reviewed on Aug. 27, 2025

Anchor at Tideline

Anchor at Tideline

3 out of 5
Price was CA $1,183, price is now CA $960 per person
CA $960
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Manchester (MHT)
10/10 Exceptional! (1 review)
Holiday Inn Express Hotel & Suites Rochester by IHG

Holiday Inn Express Hotel & Suites Rochester by IHG

2.5 out of 5
Price was CA $945, price is now CA $855 per person
CA $855
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
The breakfast could have been replenished more often.

Reviewed on Aug. 13, 2025

Ready to book your vacation to Chesterfield?

 

Choose your dates

Chesterfield Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Sep 4 to Sep 5
CA $172
CA $187 total
Sep 4 - Sep 5
includes taxes & fees
Keene Elm City Hotel, Ascend Hotel Collection
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 $154 per night from Aug 31 to Sep 1
CA $154
CA $170 total
Aug 31 - Sep 1
includes taxes & fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug. 22, 2025

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 $165 per night from Sep 4 to Sep 5
CA $165
CA $182 total
Sep 4 - Sep 5
includes taxes & fees
8/10 Very Good! (871 reviews)
"Good counter service. Nice clean room. Good tv. Good breakfast."

Reviewed on Aug. 24, 2025

Hampton Inn Brattleboro
See all 495 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
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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $740 on Expedia for your Chesterfield escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You're likely to find reduced prices and better availability in January, February and March. Check out our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organized itinerary, you can easily hit the most popular Chesterfield attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Finding a cheap Chesterfield package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Chesterfield?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Chesterfield.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Chesterfield.
  3. Work out your trip length: Think about how much time you want to spend discovering Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Chesterfield vacation package.

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