Gloucester Flight + Hotel Packages

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

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

Save 100% on your flight

per person

Jul 16 - Jul 20

found 17 hours ago

Roundtrip non-stop flight included

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

Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.

Holly Tree Resort

Save 100% on your flight

per person

Jul 11 - Jul 16

found 1 day ago

Roundtrip flight included

New York (JFK) to Boston (BOS)

Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.

Riverview Resort

Save 100% on your flight

per person

Jul 11 - Jul 16

found 1 day ago

Roundtrip flight included

New York (JFK) to Boston (BOS)

Stay at this 3-star aparthotel in South Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.

Boston Harbor Hotel

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Life House, Nantucket

Save 100% on your flight

per person

Jun 26 - Jun 30

found 1 day ago

Roundtrip flight included

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

Stay at this 3.5-star hotel in Nantucket. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions First Congregational Church and Jethro Coffin House are located nearby.

The Inn at Hastings Park, Relais & Chateaux - Boston

per person

Jul 11 - Jul 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

Stay at this 4-star luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.

The Cove At Salem

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.

Thomas Sea Suites

Save 100% on your flight

per person

Jun 26 - Jun 30

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Stay at this 3.5-star condo in Plymouth. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Plymouth Harbor and Plymouth Rock are located nearby.

Gloucester Vacation Packages 3-4 Night Stays

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

Freepoint Hotel Cambridge, Tapestry Collection by Hilton

Save 100% on your flight

per person

Jul 16 - Jul 20

found 17 hours ago

Roundtrip non-stop flight included

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

Boston Harbor Hotel

North End

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

Life House, Nantucket

Nantucket Town

Save 100% on your flight

per person

Jun 26 - Jun 30

found 1 day ago

Roundtrip flight included

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

Studio Allston Hotel

Brighton

Save 100% on your flight

per person

Jul 16 - Jul 20

found 17 hours ago

Roundtrip non-stop flight included

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