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
Price was CA $552, price is now CA $527 per person
CA $527
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
9/10 Wonderful! (1,008 reviews)
Such a charming and convenient location! Had a cozy little room, and enjoyed meals on the patio and reading in the lobby. Staff was so kind and happy to help. Would definitely come back!

Reviewed on Aug. 16, 2025

Anchor at Tideline

Anchor at Tideline

3 out of 5
Price was CA $626, price is now CA $594 per person
CA $594
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
No reviews
Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was CA $682, price is now CA $672 per person
CA $672
per person
Nov 12 - Nov 15
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
8.6/10 Excellent! (866 reviews)
super new apartment, very clean, excellent shower, good breakfast, would come back for a weekend.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Chesterfield?

 

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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 $173 per night from Aug 27 to Aug 28
CA $173
CA $188 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (880 reviews)
"Nice stay. Good value"

Reviewed on Aug. 18, 2025

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 $194 per night from Aug 21 to Aug 22
CA $194
CA $214 total
Aug 21 - Aug 22
includes taxes & fees
6.6/10 (1,006 reviews)
"Staff was helpful. Quiet area"

Reviewed on Aug. 17, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is CA $170 per night from Sep 2 to Sep 3
CA $170
CA $187 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very Good! (866 reviews)
"Great beach and nice rooms Breakfast can improve and pool is small"

Reviewed on Aug. 17, 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
Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $527 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.