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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,287, price is now CA $924 per person
CA $924
per person
Sep 7 - Sep 12
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (193 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,028, price is now CA $1,328 per person
CA $1,328
per person
Aug 12 - Aug 16
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (1,002 reviews)
Great experience but check in was delayed for a while and ended up in a different room category but hotel is beautiful and centrally located.

Reviewed on Jul 5, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,611, price is now CA $2,537 per person
CA $2,537
per person
Sep 17 - Sep 20
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $5,480, price is now CA $3,971 per person
CA $3,971
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $3,063, price is now CA $2,240 per person
CA $2,240
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 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
The price is CA $226 per night from Aug 2 to Aug 3
CA $226
CA $305 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,414 reviews)
"Everyone was amazing I wish I could remember the young lady that helped me from the front desk ! She was amazing"

Reviewed on Jul 6, 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! (4,524 reviews)
"Great hotel!"

Reviewed on Jul 6, 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! (2,714 reviews)
"We stayed in Boston for one night and it was hard to find somewhere cost effective. Therefore, we opted for this hotel on a whim, never using a shared bathroom before so we were a bit apprehensive. We were so pleasantly surprised at the room, it was very well thought out on the design and layout. ..."

Reviewed on Jul 5, 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.
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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 $924 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.

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.