COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Holidays to Rockland

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Rockland choose Expedia! Find everything you need to organise your trip to Rockland in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

DoubleTree by Hilton Boston-Rockland
DoubleTree by Hilton Boston-Rockland
3 out of 5
929 Hingham St, Rockland, MA
The price is £91 per night from 4 Mar to 5 Mar

Situated in Rockland, this hotel is within 6 miles (10 km) of South Shore Hospital, Rockland Golf Course and Wompatuck State Park. Rockland Ice Rink and Weymouth ...

4/5Very Good! (550 reviews)

"Everything was great. Felt very safe. Would stay there again."…"

Reviewed on 13 Feb 2021

DoubleTree by Hilton Boston-Rockland
Comfort Inn Rockland - Boston
Comfort Inn Rockland - Boston
2.5 out of 5
850 Hingham St, Rockland, MA
The price is £79 per night from 7 Mar to 8 Mar

Situated in Rockland, this hotel is within 6 miles (10 km) of South Shore Hospital, Rockland Golf Course and Wompatuck State Park. Rockland Ice Rink and Ames ...

3.9/5Good! (480 reviews)

"Very clean. Close to highway and restaurants. Also included free breakfast was delicous."…"

Reviewed on 26 Mar 2020

Comfort Inn Rockland - Boston
Best Western Rockland
Best Western Rockland
2.5 out of 5
909 Hingham St, Rockland, MA
The price is £78 per night from 4 Mar to 5 Mar

Situated in the business district, this hotel is within 6 miles (10 km) of South Shore Hospital, Rockland Golf Course and Wompatuck State Park. Rockland Ice ...

4/5Very Good! (995 reviews)

"Nice for the price. Would stay there again for sure."…"

Reviewed on 27 Feb 2021

Best Western 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.

Top things to do in Rockland

Plan your Rockland holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Rockland. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Rockland holiday package?
Whether it’s your hotel or flight, yes, you can amend or cancel it. Locked in your Rockland holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more details, check out our Customer Service Portal. We’re here to help you every step of the way.
When is the best time of year to visit Rockland?
If you love the excitement that comes with peak season, you’ll enjoy visiting Rockland in . If you’re seeking a more relaxed vibe, will suit you better. Don’t want to spend an arm and a leg? You might want to avoid , when things like hotels and airfares are more expensive. is generally when you’ll score the best bargains.
How far in advance should I book my Rockland holiday?
It’s hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international flights on Expedia become available to compare up to a year in advance. If you’re booking late, don’t stress. Cheap prices appear from time to time within a few weeks of departure dates.
What should I know before booking a Rockland travel package?
So many places to visit, so many things to see. With a package, you’ll be able to tick more of them off your list. Combine your hotels, rental cars and flights and land big savings.
Does Expedia offer Book Now, Pay Later Rockland holiday packages?
If you’d rather spread the price of your flight and hotel over numerous payments, Expedia is here to help. Paying the total cost of your travel upfront isn’t always the best way to pay for your escape, so we’ve teamed up with online lender Affirm to give you financial flexibility. Book Now, Pay Later and reduce the stress of saving to travel.