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Castle Island Vacation Packages

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Castle Island Flight + Hotel Packages

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

The Boston Hotel

2 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Fenway Park and Harvard Square are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 21
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 3-star beach vacation home in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Onset Beach and Shell Point Beach are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
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
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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 Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 restaurant and the bar in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 property condition in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
The Dagny Boston

The Dagny Boston

4 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
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 our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
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. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
AC Hotel by Marriott Boston Downtown

AC Hotel by Marriott Boston Downtown

3.5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
Stay at this 3.5-star business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.

3-4 Night Vacations in Castle Island

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 9 - Aug 12
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 21
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 1 - Aug 5
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 9 - Aug 12
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

5-7 Night Vacations in Castle Island

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

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 29
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)

Castle Island Last Minute Hotel Deals

Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Omni Parker House
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
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 restaurant and the helpful ...
Seaport Hotel Boston
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 breakfast and the restaurant in our reviews. ...
Hyatt Regency Boston Harbor
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
Hyatt Place Boston/Seaport District
Hyatt Place Boston/Seaport District
3 out of 5
295 NORTHERN AVENUE, Boston, MA
Stay at this 3-star business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful ...
Hyatt Place 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
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
See all 2,689 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 $534.

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 $176.

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 $534.

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.

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