Chesterfield Flight + Hotel Packages

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

Holiday Inn Express Boston North-Woburn by IHG

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attraction Burlington Mall is located nearby.

Raffles Boston

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Boston Harbor Hotel

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 Boston Harbor are located nearby.

The Westin Boston Seaport District

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.

Maverick Suites at 40 Temple St

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this aparthotel in Boston. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Boston Common and TD Garden are located nearby.

Fairmont Copley Plaza, Boston

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Revere Hotel Boston Common

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the bar in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

citizenM Boston North Station

Save 100% on your flight

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions TD Garden and Boston Harbor are located nearby.

Chesterfield Vacation Packages 3-4 Night Stays

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

Encore Boston Harbor

Save 100% on your flight

per person

Aug 25 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Boston (BOS)

Boston Harbor Hotel

North End

Save 100% on your flight

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)