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.

Cambria Hotel & Suites Plymouth

CA $677

per person

Oct 16 - Oct 20

found 3 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this 3-star hotel in Plymouth. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Colony Place and Mayflower Brewing Company are located nearby.

Boston Harbor Hotel

North End

CA $2,667

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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.

Raffles Boston

Back Bay

CA $1,483

per person

Nov 6 - Nov 9

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.

Lakeside Inn

CA $739

per person

Nov 8 - Nov 15

found 22 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews.

Maverick Suites at 402 Columbus Ave

South End

CA $1,474

per person

Oct 19 - Oct 25

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Stay at this aparthotel in Boston. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions Copley Square and Boston Common are located nearby.

The Colonnade Hotel Back Bay

Back Bay

CA $1,961

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.

Frequently asked questions

How much are vacation packages to Castle Island?

A fantastic CA $677 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.

Top Castle Island hotel deals

Seaport Hotel Boston

1 Seaport Lane, Boston, MA

Free cancellation

Reserve now, pay when you stay

CA $321

CA $381 total

Sep 4 - Sep 5

includes taxes & fees

Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Pool

Pet-friendly

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free cancellation

Reserve now, pay when you stay

CA $378

CA $497 total

Sep 21 - Sep 22

includes taxes & fees

Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Pool

Hot tub

Hyatt Regency Boston Harbor

101 Harborside Drive, Boston, MA

Free cancellation

Reserve now, pay when you stay

CA $330

CA $414 total

Sep 21 - Sep 22

includes taxes & fees

Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.

Free airport shuttle

Pet-friendly

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.