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.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $1,077, price is now CA $764 per person
CA $764
per person
Jan 8 - Jan 10
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The hotel grounds are extremely well maintained; the views of the water and benches to relax on are fantastic! We had a great stay with our two teenagers. It was out of the hustle and bustle of the city. A wonderful place!

Reviewed on Oct 26, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,539, price is now CA $982 per person
CA $982
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Great hotel for the weekend! My husband and I were celebrating our anniversary!

Reviewed on Oct 25, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,334, price is now CA $935 per person
CA $935
per person
Jan 8 - Jan 10
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on Oct 20, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was CA $2,540, price is now CA $1,817 per person
CA $1,817
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,218, price is now CA $1,676 per person
CA $1,676
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

Ready to book your vacation to Rockland?

 

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Rockland Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Nov 26 to Nov 27
CA $258
CA $357 total
Nov 26 - Nov 27
includes taxes & fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Nov 26 to Nov 27
CA $145
CA $169 total
Nov 26 - Nov 27
includes taxes & fees
The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Nov 26 to Nov 27
CA $190
CA $269 total
Nov 26 - Nov 27
includes taxes & fees
9.6/10 Exceptional! (5,160 reviews)
"."

Reviewed on Oct 26, 2026

Seaport Hotel Boston
See all 3,537 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.
All Inclusive Vacations
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Beach Vacations
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Family Vacations
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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.
See properties

What to do in Rockland

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $69
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Rockland

Frequently asked questions

How much does a Rockland vacation package cost?
You'll find cheap prices from CA $764 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.