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.
Home2 Suites By Hilton Kittery
Price was CA $1,852, price is now CA $1,291 per person
CA $1,291
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (103 reviews)
Very close to Kittery and the sights. Very clean and very new (recently built). Breakfast was okay.
Reviewed on Jun 7, 2026
Sea Crest Beach Resort
Price was CA $2,178, price is now CA $1,352 per person
CA $1,352
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.8/10 Good! (292 reviews)
Tough stay this weekend, no housekeeping, very dirty bathroom puppy weekend but never received gift voucher even booked a third night spent so much hard earned $ no hospitality no communication very bad experience.
Reviewed on Jun 8, 2026
Boston Harbor Hotel
North End
Price was CA $2,951, price is now CA $1,833 per person
CA $1,833
per person
Aug 20 - Aug 23
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again
Reviewed on May 25, 2026
Nantucket Inn
Price was CA $3,384, price is now CA $2,289 per person
CA $2,289
per person
Jul 11 - Jul 15
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (700 reviews)
This was my first trip to Nantucket and probably my last. I found the hotel to be nothing special. The garden grounds were not neat and were filled with leaves. No one came to clean the room on our first day there, even though the cleaning staff was in the next room when we left for the day. I finally had to text them late in the afternoon to have someone clean the room. We couldn't find the hotel shuttle when we came in on the ferry, as they assured me they would be a van waiting. The bar closes at 10 p.m. and the only place to eat at the hotel closes at 3 p.m.
Reviewed on Jun 4, 2026
The Langham, Boston
Downtown Boston
Price was CA $2,333, price is now CA $1,637 per person
CA $1,637
per person
Aug 20 - Aug 23
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
This hotel is in the financial district. The sites are walking distance if you're a walker. The lounge is an added charge. Food was fresh but selection limited.
Reviewed on Jun 7, 2026
Rockland Hotel Deals
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Jul 5 to Jul 6
CA $200
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,673 reviews)
"Location"
Reviewed on Jun 10, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Jun 14 to Jun 15
CA $289
CA $393 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (4,711 reviews)
"My favorite hotel in Boston. Feels like a destination resort….multiple restaurants, year round rooftop outdoor pool, spa, sports bar, and everything nearby."
Reviewed on Jun 10, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $264 per night from Jul 5 to Jul 6
CA $264
CA $355 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (4,445 reviews)
"This was a decent hotel overall. The best part is the location to restaurants and boardwalk. It was in South Boston the calmer side of Boston as North Boston is where all the action is with tourists. I feel the amenities could have been better considering you are charged a daily resort fee. The pool ..."
Reviewed on Jun 11, 2026
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.
Discover the most popular places to visit in Rockland
Fenway Park
4.5/5(310 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
TD Garden
4.5/5(244 reviews)
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
Boston Harbor
4.5/5(93 reviews)
Adore Boston’s charming working harbor from the waterfront or head out by boat to get to know it more intimately.
What to do in Rockland
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
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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.
