Rockland Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Rockland

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 S$259 per night from 26 Dec to 27 Dec
S$259
includes taxes & fees
26 Dec - 27 Dec
9.6/10 Exceptional! (2,591 reviews)
"Excellent property with friendly and welcoming staff. We would definitely stay again!"

Reviewed on 22 Nov,2024

Seaport Hotel Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$242 per night from 27 Dec to 28 Dec
S$242
includes taxes & fees
27 Dec - 28 Dec
8.2/10 Very Good! (3,294 reviews)
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Reviewed on 24 Nov,2024

Hilton Boston Park Plaza
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$293 per night from 28 Nov to 29 Nov
S$293
includes taxes & fees
28 Nov - 29 Nov
8.8/10 Excellent! (2,876 reviews)
"Great location for walking around. The staff at the Omni is top notch. We have come back to this hotel for the past 7 years and will continue!"

Reviewed on 24 Nov,2024

Omni Parker House
See all 2,802 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.

Frequently asked questions

How much does a Rockland holiday package cost?
Get your credit card ready, because a trip to Rockland starts from only . When you combine your hotels, flights and car rentals into a travel package, you’ll pick up great deals.
How do I get a cheap travel package to Rockland?
Our Rockland holiday packages promise plenty of savings for the savvy traveller. For the best deal, simply bundle your hotel, flights and rental cars into a convenient package. But bargain prices are only the start of your next big adventure. When you book with Expedia, you’ll have more than 550 air carriers and 1,000,000 hotel options across the globe to choose from. No matter your budget, there’s a package that’s perfect for you.
Where should I stay in Rockland?
If you plan to visit Rockland Ice Rink, maximize your time sightseeing and find someplace to stay nearby. It’s one of the most popular attractions in this neighbourhood.
What are the top hotels in Rockland?
Comfort Inn Rockland - Boston and DoubleTree by Hilton Boston - Rockland are a couple of the most sought-after properties in Rockland. Why not take a look at the facilities and amenities at each and then make a decision?
How far in advance should I book my Rockland holiday?
Browse Expedia to compare international fares ASAP. You can usually purchase a ticket up to a year before departure. If you don’t see your preferred carrier, or you’ve left things to the last moment, don’t worry. Cheap tickets to Rockland sometimes occur a few weeks before departure.
What does an Expedia Rockland travel package include?
That depends on what you’re after. If you’re travelling solo, you might decide to bundle hotels and flights. Taking the whole family to Rockland? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Rockland travel package?
So many places to explore, so many things to do. With a package, you’ll be able to cross more of them off your list. Bundle your hotels, rental cars and flights and get ready to save.
Can I choose my airline with a Rockland Expedia holiday package?
Definitely. Expedia has more than 550 airline partners to select from worldwide. With all that choice, finding the ideal carrier to fly you to Rockland will be easy.
If I'm not able to travel, can I cancel my Rockland holiday package?
Don’t worry if you’re rethinking your Rockland holiday package — you can cancel or change your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’ll take care of it.

Popular places to visit

Fenway Park showing a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

What to do in Rockland

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$99
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Admission Tickets

View Boston Observation Deck Admission Tickets

S$34
Per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
Whale-Watching Cruise in Stellwagen Bank Marine Sanctuary

Boston Harbor New England Aquarium Whale-Watching Cruise

S$107
Per adult
86% of travellers recommend
Boston Harbor New England Aquarium Whale-Watching Cruise
See all activities in Rockland

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.