Rockland Vacations from $293

Book a Hotel + Flight or Car together to unlock savings

Photo by Janine Edmondson

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.
Best Western Springfield West Inn

Best Western Springfield West Inn

2.5 out of 5
Price was $437, price is now $293 per person
$293
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
7.8/10 Good! (1,001 reviews)
My room was comfortable and clean

Reviewed on Aug 21, 2025

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $662, price is now $394 per person
$394
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)
Great location and super convenient to waterfront dining

Reviewed on Aug 24, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Nov 12 - Nov 17
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (474 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $1,218, price is now $836 per person
$836
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug 25, 2025

The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
Price was $758, price is now $539 per person
$539
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,108 reviews)
Breakfast buttet was awesome, i just wished i was hungry.

Reviewed on Aug 26, 2025

Don't see what you're looking for?
See all available trips from Columbus to Rockland
View all trips

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
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

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (3,273 reviews)
"Our second stay at the Seaport Hotel and everything was amazing. We will continue to use this hotel for all of our Boston visits."

Reviewed on Aug 24, 2025

Seaport Hotel Boston
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
$225 nightly
The price is $262 total per night from Sep 1 to Sep 2
$262 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (3,868 reviews)
"Great hotel, nice staff, cool area"

Reviewed on Aug 25, 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
$184 nightly
The price is $214 total per night from Sep 1 to Sep 2
$214 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (3,699 reviews)
"Get a room with the city view, it is amazing. Surprising, that they don’t offer gluten free options at their much advertised breakfast."

Reviewed on Aug 25, 2025

citizenM Boston North Station
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Rockland vacation package cost?
You can snap up a vacation package to this top destination from $293 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

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.