Rockland Vacation Packages
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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.
Top Rockland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $964
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,851
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
For the most high end hotel in Boston, lacked updated amenities that other newer hotels have. Rooms were severely dated.
Reviewed on Oct 20, 2026
Ready to book your vacation to Rockland?
Rockland Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $303
CA $410 total
Nov 20 - Nov 21
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $222
CA $259 total
Nov 8 - Nov 9
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $264
CA $356 total
Nov 21 - Nov 22
includes taxes & fees
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.
Stay near popular Rockland attractions
Rockland Ice Rink
8.6/10 (12 reviews)
Enjoy an outing to Rockland Ice Rink during your stay in Rockland. Stroll along the area's seaside, or simply savor its top-notch restaurants.
Howland Park
After visiting Howland Park, make a plan to see the other sights and activities in Rockland. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Rockland Town Forest
You can take time to visit Rockland Town Forest during your travels to Rockland. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Rockland Golf Course
8.2/10 (10 reviews)
Enjoy a round of golf in Rockland at Rockland Golf Course. Stroll along the area's seaside, or simply savor its top-notch restaurants.
Rockland Memorial Library
Rockland Memorial Library is just one of the places to see in Rockland, so why not enjoy the other things to explore during your travels? Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Major Reed Park
Major Reed Park is just one of the places to see in Rockland, so why not enjoy the other things to explore during your travels? Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Rockland Town Hall
After visiting Rockland Town Hall, make a plan to see the other sights and activities in Rockland. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Bicentennial Park
Bicentennial Park is just one of the places to see in Rockland, so why not enjoy the other things to explore during your travels? Visit the shops in this family-friendly area, or simply enjoy its restaurants.
What to do in Rockland
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Frequently asked questions
How much does a Rockland vacation package cost?
You'll find cheap prices from CA $645 on Expedia for your Rockland escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Rockland costs.
What are the cheapest months to go to Rockland?
January, February and March are the best times to look for cheap Rockland vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Rockland?
When planning your Rockland vacation, a few days will be enough to tour the highlights. Make sure to stop by Lake Street Beach — it's one of the major attractions in this destination. If you're looking for more adventure, think about basing yourself here and setting off on some day tours from Rockland.
Is it worth booking a vacation package to Rockland?
It's no wonder a Rockland vacation is on the to-do list of many travellers. Well-known attractions like Rockland Ice Rink are just the beginning of things to keep you busy here.
How to find the best Rockland package deals?
Landing a cheap Rockland package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Rockland package deals. Want a simple trick to get the biggest 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 make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Rockland vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Rockland?
If you're planning an impromptu Rockland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Rockland?
- Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to vacation in Rockland.
- Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Rockland.
- Set the duration of your trip: Start by making a list of all the attractions you want to get to in Rockland. Then, estimate how long you'll need at each, along with any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Rockland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
