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 Charles Hotel
West Cambridge
Price was CA $1,398, price is now CA $921 per person
CA $921
per person
Sep 10 - Sep 13
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,011 reviews)
The Charles Hotel exceeded expectations on every front. The rooms and common areas were spotless, and the amenities felt genuinely upscale. Staff were accommodating and allowed us extra time to check out, which made the end of our stay stress-free. On-site parking was a huge plus, and the location couldn’t be better — just steps from Harvard Square, with great restaurants and shops within easy walking distance. Highly recommend for anyone visiting the area.
Reviewed on Jul 17, 2026
The Newbury Boston
Back Bay
Price was CA $1,887, price is now CA $1,005 per person
CA $1,005
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.4/10 Exceptional! (670 reviews)
We were first greeted by Andrew who was so welcoming and knowledgeable. Suprisingly we were upgraded to a corner room on the 16th floor...so beautiful! Then we were escorted to the room by Chad who gave great tips on how to navigate the elevators and the room.
We stayed a week and took advantage of the awesome location, great restaurants (Street Bar and Contessa). The library room had coffee with pastries in the morning and treats at night...we loved out stay and would come back in a heartbeat!
Reviewed on Jul 18, 2026
Luxury Apartments by Hyatus at Boston Everett
Price was CA $2,098, price is now CA $1,397 per person
CA $1,397
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (5 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week.
We did not have a rental car but the parking garage was easily accessible and secure.
We were able to get ubers very easily from the location.
The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient.
The support staff replied to all our messages in the chat option quickly and were very helpful.
The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred.
Would recommend this place without hesitation.
Reviewed on Jun 15, 2026
Rockland Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $265 per night from Aug 2 to Aug 3
CA $265
CA $357 total
Aug 2 - Aug 3
includes taxes & fees
9.6/10 Exceptional! (4,582 reviews)
"We had the king harbor view and it was one of the best hotel rooms we’ve ever stayed in, large, comfortable, beautiful and fabulous views! Worth the extra money! Everything was meticulously clean and staff was very helpful. Walter was particularly helpful."
Reviewed on Jul 19, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Aug 16 to Aug 17
CA $201
CA $234 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (2,748 reviews)
"It was clean, the staff was helpful. There was no maid service. We realized after a couple of days and the trash built up and the towels never dried. We asked for clean towels and they were delivered. The room was smaller than a small camper. The bed filled the room so one of us had to crawl over ..."
Reviewed on Jul 20, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $335 per night from Jul 31 to Aug 1
CA $335
CA $448 total
Jul 31 - Aug 1
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
What to do in Rockland
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $68
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $119
per adult
92% of travellers recommend
Frequently asked questions
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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.
