Rockland Vacations from $331

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Your Rockland Vacation

Known for its rich history and coastal scenery, Rockland is a perfect getaway destination. Book one of our Rockland vacation packages and experience all that this exciting city has to offer. If sightseeing is part of the plan during your trip to Rockland, swing by major attractions like Rockland Ice Rink, Rockland Golf Course and Lake Street Beach. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Rockland vacation is a walk in the park with Expedia.

The Latest Rockland vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $819, price is now $331 per person
$331
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $1,761, price is now $931 per person
$931
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on Oct 7, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $880, price is now $556 per person
$556
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (246 reviews)
Lean room, nice staff but the elevator broke and it took a while to fix it

Reviewed on Oct 1, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,345, price is now $855 per person
$855
per person
Dec 26 - Dec 29
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Hotel was clean and the room was a great size. Staff was very helpful.

Reviewed on Oct 10, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $823, price is now $532 per person
$532
per person
Dec 24 - Dec 27
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Absolutely charming place, with a great location within Cambridge. I will definitely stay here again in the future!

Reviewed on Oct 10, 2025

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Discover the most popular places to visit in Rockland

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Rockland

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

$49
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Rockland

Rockland Hotel Deals

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $150 total per night from Nov 11 to Nov 12
$150 total
Nov 11 - Nov 12
Total with taxes and fees
8.8/10 Excellent! (2,159 reviews)
"The staff were incredibly helpful! Accommodation, although slightly unuasal, not having a en-suite bathroom in the room, it was easy, safe, convenient having it down the hall. This arrangement made the cost about half of a compreable room elsewhere and the condition and decor of the rooms and hotel ..."

Reviewed on Oct 9, 2025

The Revolution Hotel
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $255 total per night from Nov 9 to Nov 10
$255 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (3,904 reviews)
"Very clean and kind staff"

Reviewed on Oct 11, 2025

citizenM Boston North Station
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
$279 nightly
The price is $325 total per night from Oct 31 to Nov 1
$325 total
Oct 31 - Nov 1
Total with taxes and fees
9.4/10 Exceptional! (6,555 reviews)
"Multiple restaurants nearby and close to the harbourwalk. But with multiple resturants and single pane windows you will hear a lot of noise on the weekends. The Irish Pub nearby has live music that makes its way into your room. You also hear the hum of the mini fridge. For those reallt sensitive ..."

Reviewed on Oct 6, 2025

The Dagny Boston
See all 3,320 properties in Rockland
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.

Rockland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
18,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Nantasket Beach Reservation, Minot Beach and Stellwagen Bank National Marine Sanctuary

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Frequently asked questions

How much does a Rockland vacation package cost?
You can snap up a vacation package to this top destination from $331 on Expedia. But how much your vacation to Rockland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Rockland?
November, December and January are great times to search for cheap Rockland vacation packages. Traveling in less busy months means you can usually find better prices on flights and accommodations.
How many days is enough for Rockland?
With a well-planned schedule, you can easily hit the main Rockland attractions in a few days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Rockland vacation for longer.
Is it worth booking a vacation package to Rockland?
It's easy to see why a Rockland vacation is on the must-do list of many travelers. Major attractions like Rockland Ice Rink are just the start of things to keep you busy here.
How to find the best Rockland package deals?
Bagging a cheap Rockland package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Rockland package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Rockland vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Rockland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Rockland?
Score incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Rockland trip.
Does Expedia offer Book Now, Pay Later Rockland vacation packages?
Jet off on your perfect trip to Rockland with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snap up bargains while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.