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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.
The Latest Chesterfield vacation packages

Hotel Coolidge
Reviewed on Aug 18, 2025

The Centennial
Reviewed on Aug 18, 2025


Cold Spring Plymouth Resort
Reviewed on Aug 17, 2025

Discover the most popular places to visit in Chesterfield
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.
Chesterfield Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection
Reviewed on Aug 18, 2025

Colonial Motel And Spa
Reviewed on Aug 17, 2025

Hampton Inn Brattleboro
Reviewed on Aug 17, 2025
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- Spofford Lake
- Madame Sherri Forest
- Visit West Chesterfield
- Madame Sherris Castle Ruins
- Visit Spofford
- United States Navy Seabee Bridge
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- Stonewall Farm
- Visit Hinsdale
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- Cheshire Children's Museum
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