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.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $1,166, price is now CA $810 per person
CA $810
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
Great hotel staff, great location, great room :)

Reviewed on Jul 8, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,473, price is now CA $2,184 per person
CA $2,184
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,019, price is now CA $1,338 per person
CA $1,338
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,956, price is now CA $1,320 per person
CA $1,320
per person
Aug 21 - Aug 25
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Staff was super friendly and accommodating, and we very much enjoyed our stay. Room was good, location is great right on the edge of town and easily accessible.

Reviewed on Jul 8, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $2,260, price is now CA $1,546 per person
CA $1,546
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (432 reviews)
This goes into one of the top hotels I've ever stayed at. I seriously can't think of a single complaint. They gave us the best view of the Boston fireworks on the top floor, and took care of us every step of the way. They even had a big TV set up in the lobby for the World Cup games. The front desk people were super nice, and Ivan was our favorite server!

Reviewed on Jul 7, 2026

Ready to book your vacation to Rockland?

 

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Rockland Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Jul 26 to Jul 27
CA $237
CA $318 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (2,430 reviews)
"Poor bar closed early nowhere to get breakfast early"

Reviewed on Jul 8, 2026

Hyatt Regency Boston/Cambridge
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 $268 per night from Jul 26 to Jul 27
CA $268
CA $361 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,541 reviews)
"The Seaport Hotel was great. Lots of fun events nearby and the hotel was clean, with a great staff"

Reviewed on Jul 8, 2026

Seaport Hotel Boston
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 $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,726 reviews)
"Great hotel. Loved the vibe and room was great!"

Reviewed on Jul 8, 2026

The Revolution Hotel
See all 3,633 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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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 beautiful beaches, 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 $73
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
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $39
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Rockland

Frequently asked questions

How much does a Rockland vacation package cost?
You'll find cheap prices from CA $810 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.

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