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Castle Island Vacation Packages

Castle Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Stay at this 4-star hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Dec 25 - Dec 29
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Stay at this 4-star boutique 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 Burlington Mall and Lexington Battle Green are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Dec 25 - Dec 29
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

2.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Book a stay at this business-friendly hotel in Watertown. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Homewood Suites by Hilton Boston/Cambridge-Arlington, MA

Homewood Suites by Hilton Boston/Cambridge-Arlington, MA

3 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Arlington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Encore Boston Harbor are located nearby.
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Boston (BOS)
Stay at this 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 Faneuil Hall Marketplace are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Newbury Boston

The Newbury Boston

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this eco-certified 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.
The Boxer

The Boxer

4 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.

3-4 Night Vacations in Castle Island

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

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Dec 30 - Jan 2
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Dec 25 - Dec 29
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Dec 31 - Jan 3
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)

5-7 Night Vacations in Castle Island

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

2.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Homewood Suites by Hilton Boston/Cambridge-Arlington, MA

Homewood Suites by Hilton Boston/Cambridge-Arlington, MA

3 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)

Castle Island Last Minute Hotel Deals

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
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 ...
Seaport Hotel Boston
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Omni Boston Hotel at the Seaport
Hyatt Regency Boston Harbor
Hyatt Regency Boston Harbor
4 out of 5
101 Harborside Drive, Boston, MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our ...
Hyatt Regency Boston Harbor
Hampton Inn Boston Seaport District
Hampton Inn Boston Seaport District
3 out of 5
670 Summer Street, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hampton Inn Boston Seaport District
The Westin Boston Seaport District
The Westin Boston Seaport District
4 out of 5
425 Summer St, Boston, MA
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 ...
The Westin Boston Seaport District
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
Stay at this 4-star historic hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in ...
The Dagny Boston
Homewood Suites by Hilton Boston Seaport District
Homewood Suites by Hilton Boston Seaport District
3 out of 5
670 Summer Street, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Homewood Suites by Hilton Boston Seaport District
Hilton Boston Logan Airport
Hilton Boston Logan Airport
4 out of 5
One Hotel Drive, Boston, MA
Stay at this 4-star business-friendly hotel in Boston. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the restaurant ...
Hilton Boston Logan Airport
See all 2,678 properties in Castle Island
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.

Book the perfect getaway to Castle Island

With Hotwire, booking your next trip to South Boston is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Castle Island while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Castle Island flight and hotel package for as low as $241.

Living it up in South Boston means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Castle Island, South Boston vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Castle Island for some of the best accommodations and flight deals.

FAQs about cheap Castle Island packages:

How to get cheap vacation deals to Castle Island?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $120.

How much are Castle Island packages?

Vacation packages to Castle Island vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $241.

How to find cheap car rentals near Castle Island?

Hotwire partners with some of the most reliable car rental companies in South Boston to bring you the best car rental deals in Castle Island for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Castle Island now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Castle Island right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.