Rockland Holidays
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Top Flight + Hotel Deals in Rockland
Price found within the past 48 hours. Click for updated prices.
Furnished Apartment Near Longwood
North Brookline
€1,075
per person
29 Oct - 4 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
7/10 Good! (6 reviews)
Super cute apartment! Stayed the weekend to visit out soon at college. Locations was close to everything beds were super comfortable, would stay here again.
Reviewed on 13 Sept 2026
Top hotels in Rockland
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
€286
25 Oct - 26 Oct
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
€276
25 Oct - 26 Oct
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
€239
25 Oct - 26 Oct
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
Rockland Ice Rink
8.6/10 (12 reviews)
This welcoming community ice rink has served local skaters since 1972 with quality ice surfaces. Enjoy figure skating lessons, hockey leagues, or casual glides during public sessions in this year-round indoor facility.
Rockland Town Forest
This whimsical forest trail features painted rocks and artistic installations along its serene paths. Discover charming bridges over French's Stream while keeping an eye out for hidden treasures tucked among the trees.
Rockland Golf Course
8.2/10 (10 reviews)
Rockland Golf Course features the longest 18-hole par-3 course east of the Mississippi, where precision trumps power. Play among majestic oaks and streams, then relax at the Rock Bar and Restaurant.
Howland Park
Howland Park offers a peaceful green retreat in Rockland, Massachusetts, perfect for leisurely strolls. Located near the Mark Bavis Sports Complex, it combines outdoor relaxation with recreation.
Major Reed Park
Major Reed Park offers tranquil trails and open spaces for picnics and outdoor recreation in Rockland. Spring and fall visits reward with pleasant weather and vibrant natural surroundings.
Rockland Memorial Library
This historic Carnegie library combines architectural charm with a vibrant community hub. Browse the extensive collection, join a yoga class, or simply soak in the cosy atmosphere perfect for quiet study.
Bicentennial Park
This community hub offers a quarter-mile track, football fields, and a shaded playground for all ages. Connect with local life while enjoying the park's proximity to Rockland Rail Trail for extended outdoor adventures.
Hartsuffs Park
This serene 16.5-acre retreat offers wooded trails and a seasonal swimming pond. Rockland residents can enjoy disc golf among the trees or bring children to explore the playground.
What to do in Rockland
Boston Old Town Trolley Hop-on Hop-Off City Tour
€42
per adult
90% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
€61
per adult
80% of travellers recommend
View Boston Observation Deck General Admission
€29
per adult
Frequently asked questions
How much does a Rockland holiday package cost?
You can snap up a holiday package to this top destination from €853 on Expedia. But how much your holiday to Rockland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Rockland?
January, February and March are the best times to search for cheap Rockland holiday packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and accommodation.
How many days is enough for Rockland?
With a well-planned schedule, you can easily hit the main Rockland sights in a handful of days. But if you want to venture off the beaten track or go on day trips, think about booking your Rockland holiday for longer.
Is it worth booking a holiday package to Rockland?
Rockland offers everything you need for an unforgettable trip. Begin your Rockland holiday on a high note by visiting popular attractions like Rockland Ice Rink.
How to find the best Rockland package deals?
Bagging a cheap Rockland package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Rockland package deals. Want a simple trick to score even more 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 holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Rockland holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Rockland?
Score incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Rockland trip.
How to plan a trip to Rockland?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Rockland.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will likely be the largest expense during your trip to Rockland.
- Decide how long to go away for: Now that you know more about Rockland, you can figure out the ideal length of your holiday. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
- Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the ideal Rockland holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
