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Cape Ann Vacation Packages

Cape Ann Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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 Dagny Boston

The Dagny Boston

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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.
The Bostonian Boston

The Bostonian Boston

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, room service, and a health club. 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.
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 4-star boutique 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 Faneuil Hall Marketplace are located nearby.
The Boxer

The Boxer

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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.
Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station

3 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 3-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 TD Garden and Faneuil Hall Marketplace are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) 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.
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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 Boston Harbor are located nearby.

3-4 Night Vacations in Cape Ann

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
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)

5-7 Night Vacations in Cape Ann

Price found within the past 48 hours. Click for updated prices.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Nov 9 - Nov 16
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)

Cape Ann Last Minute Hotel Deals

Rockport Inn And Suites
Rockport Inn And Suites
2.5 out of 5
183 Main Street, Rockport, MA
Stay at this B&B in Rockport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ...
Rockport Inn And Suites
The Seafarer Inn
The Seafarer Inn
3 out of 5
50 Marmion Way, Rockport, MA
Stay at this 3-star B&B in Rockport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Old Garden Beach and Straightsmouth Island Lighthouse ...
The Seafarer Inn
Sally Webster Inn
Sally Webster Inn
3 out of 5
34 Mt Pleasant St, Rockport, MA
Stay at this 3-star B&B in Rockport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Ann and Good Harbor Beach are located ...
Sally Webster Inn
Addison Choate Inn
Addison Choate Inn
3.5 out of 5
49 Broadway, Rockport, MA
Stay at this 3.5-star B&B in Rockport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Addison Choate Inn
The Cove at Rockport Hotel
The Cove at Rockport Hotel
2 out of 5
1 King St, Rockport, MA
Stay at this hotel in Rockport. Enjoy free WiFi, free parking, and bathrobes. Our guests praise the helpful staff in our reviews. Popular attractions Cape Ann ...
The Cove at Rockport Hotel
See all 468 properties in Cape Ann
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 Cape Ann

With Hotwire, booking your next trip to Rockport 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 Cape Ann 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 Cape Ann flight and hotel package for as low as $368.

Living it up in Rockport means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Cape Ann, Rockport 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 Cape Ann for some of the best accommodations and flight deals.

FAQs about cheap Cape Ann packages:

How to get cheap vacation deals to Cape Ann?

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 $189.

How much are Cape Ann packages?

Vacation packages to Cape Ann 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 $368.

How to find cheap car rentals near Cape Ann?

Hotwire partners with some of the most reliable car rental companies in Rockport to bring you the best car rental deals in Cape Ann 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 Cape Ann now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Cape Ann 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.