Castle Island Vacation Deals: Castle Island, South Boston Holidays

Castle Island vacation package deals

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

Holly Tree Resort by VRI Americas

Save 100% on your flight

per person

Mar. 27 - Apr. 3

found 2 days ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cape Cod Inflatable Park and Englewood Beach are located nearby.

Boston Harbor Hotel

North End

Save 100% on your flight

per person

May 2 - May 5

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) 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 Common are located nearby.

Fairmont Copley Plaza, Boston

Back Bay

Save 100% on your flight

per person

May 3 - May 7

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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 Boston Common and Fenway Park are located nearby.

Sea Mist Resort by VRI Americas

Save 100% on your flight

per person

Mar. 27 - Apr. 3

found 2 days ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 3-star business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Mashpee Commons and Cape Cod Children's Museum are located nearby.

Raffles Boston

Back Bay

Save 100% on your flight

per person

Mar. 13 - Mar. 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

per person

May 4 - May 8

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Boston (BOS)

Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.

Frequently asked questions

How much are vacation packages to Castle Island?

A fantastic CA $823 package deal can be booked for your upcoming trip to Castle Island. Why not let Travelocity take the hard work out of organizing your vacation? The great part about combining your hotel and flights is that it’ll save you a pretty penny. And there’s nothing better than extra cash in your pocket!

Where can I get the best vacation package deals for Castle Island?

Travelocity has countless ways to score a sensational Castle Island package deal. Choose from 400 partner airlines and 665,000 properties all over the globe and create a vacation package that’s suited to you. With so much choice, now’s the time to book your next big getaway.

Why should I purchase my Castle Island vacation package with Travelocity?

From incredible destinations to memorable experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also make sure you’re being taken care of before, during and after your vacation. And don’t fret if you spot a lower price on your reservation, we’ll match it. That’s our Price Match Guarantee.

Can I go on vacation to Castle Island at this time?

Discover all the info you should know about quarantine policies and travel restrictions before you fly to Castle Island. Our Covid-19 Travel Advisor is full of useful advice to help make your vacation relaxed and hassle-free.