Rockland Vacations from $180

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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.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
Price was $282, price is now $180 per person
$180
per person
Oct 23 - Oct 26
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.6/10 Good! (456 reviews)
Staff was very friendly and helpful

Reviewed on Aug 23, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $650, price is now $329 per person
$329
per person
Nov 1 - Nov 3
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $698, price is now $430 per person
$430
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,007 reviews)
Beautiful area, easy to walk around and sightsee. Room was spacious but has a chlorine smell, average for cleanliness. Dirt, grime around shower doors.

Reviewed on Aug 22, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $514, price is now $317 per person
$317
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,226 reviews)
Consistently excellent stay

Reviewed on Aug 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
Price was $387, price is now $245 per person
$245
per person
Oct 23 - Oct 26
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great location, very comfortable beds. The lighting in the room could be better.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
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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

4.5/5(2,499 reviews)

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

4.5/5(1,966 reviews)

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

4.5/5(4,786 reviews)

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
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$70
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

$30
per traveler
Liberty, Freedom, and Revolution: American History Tours Bundle
See all activities in Rockland

Rockland Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (3,837 reviews)
"Overall a great hotel. Well located, the seaport zone is really beautiful. Public transportation access"

Reviewed on Aug 21, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $203 total per night from Aug 24 to Aug 25
$203 total
Aug 24 - Aug 25
Total with taxes and fees
9.2/10 Wonderful! (3,682 reviews)
"Great location, the staff were very friendly."

Reviewed on Aug 22, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $182 total per night from Sep 1 to Sep 2
$182 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (3,265 reviews)
"This hotel is not the least expensive but you certainly get what you pay for. It was unbelievable how nice the staff was, how good the food was in or Aura restaurant (they catered to vegan and vegetarian people). We went for a concert, and the venue was literally across the street!"

Reviewed on Aug 21, 2025

Seaport Hotel Boston
See all 3,319 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.

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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 $180 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.