Chesterfield Flight + Hotel Packages

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Hilton Garden Inn Hartford South/Glastonbury

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per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

New York (JFK) to Hartford (BDL)

Stay at this 3-star business-friendly hotel in Glastonbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Xfinity Theatre and Glastonbury Historic District are located nearby.

Las Flores Villa

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per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

New York (JFK) to Hartford (BDL)

Stay at this 5-star luxury vacation home in New Preston. Enjoy free WiFi, free parking, and private pools. Popular attractions Hopkins Vineyard and Lake Waramaug are located nearby.

YOTEL Boston

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per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Boston (BOS)

Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Maverick Suites at 89 Marion

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per person

Oct 30 - Nov 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this aparthotel in Brookline. Enjoy free WiFi and laundry facilities. Our guests praise the clean rooms in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.

Beauport Hotel Gloucester

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per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Good Harbor Beach and Wingaersheek Beach are located nearby.

By the Sea Guests Bed & Breakfast & Suites

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per person

Sep 20 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Stay at this 3.5-star beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.

Parker Beach Lodge

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per person

Sep 20 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Stay at this 3-star hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Thachers Beach are located nearby.

Sesuit Harbor House

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per person

Sep 20 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Boston (BOS)

Stay at this 3-star hotel in Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mayflower Beach and Scargo Tower are located nearby.

Chesterfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.