A calm sea with multiple sailboats anchored, a distant ship, and a hazy shoreline.

Rockland Holiday Rentals

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Our top choices for Rockland holiday rentals

1. Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (59 reviews)
"Great overall stay!"
United States
Chris R.
The price is AU$629
includes taxes & fees
2 Nov - 3 Nov
Cozy three-bedroom home close to Boston w/ plenty of parking

2. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (53 reviews)
"Extraordinarily beautiful VRBO, very clean, convenient to highway, walking distance to several eateries, walk or quick drive to the Red Line to use to get into downtown Boston, and very responsive owner."
United States
Mark T.
The price is AU$611
includes taxes & fees
27 Oct - 28 Oct
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

3. Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
Quincy
9.8 out of 10, Exceptional, (8 reviews)
"Perfect stay for the night. Communication was great and property was clean and had everything we needed."
United States
Ryan E.
The price is AU$408
includes taxes & fees
1 Nov - 2 Nov
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams

4. 4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

4BR 6BEDS WOLLASTON BEACH. NearBOSTON3
Quincy
10.0 out of 10, Exceptional, (47 reviews)
"Kim was great in regards to communication and and answered all my questions and was very accommodating! We enjoyed our stay and the kids loved playing at the beach too as it was a couple minute walk :) Theres a playground nearby which helped out a lot too!"
United States
Jennifer V.
4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

5. Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Quincy
9.6 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is AU$610
includes taxes & fees
25 Oct - 26 Oct
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (678 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is AU$475
includes taxes & fees
23 Nov - 24 Nov
Marriott Vacation Club® at Custom House, Boston

7. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Quincy
9.6 out of 10, Exceptional, (55 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is AU$610
includes taxes & fees
25 Oct - 26 Oct
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

8. Spacious 6BR Quincy Beach Near Boston | Family Vacation & Pet-Friendly 555

Spacious 6BR Quincy Beach Near Boston | Family Vacation & Pet-Friendly 555
Quincy
9.8 out of 10, Exceptional, (39 reviews)
"Great, spacious property for a family stay & clear communication with host. "
United States
Amber M.
The price is AU$826
includes taxes & fees
26 Oct - 27 Oct
Spacious 6BR Quincy Beach Near Boston | Family Vacation & Pet-Friendly 555

9. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is AU$407
includes taxes & fees
29 Oct - 30 Oct
Kasa Boston at Fenway

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (41 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is AU$369
includes taxes & fees
9 Nov - 10 Nov
The Chester Hotel

11. Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (131 reviews)
"Great location, clean and the room setup is perfect for family."
United States
Heather
The price is AU$583
includes taxes & fees
25 Oct - 26 Oct
Thomas Sea Suites

12. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (767 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is AU$350
includes taxes & fees
22 Nov - 23 Nov
Global Luxury Suites Downtown Boston

13. Scituate Seaside Escape – Sleeps 8, Walk to Beach

Scituate Seaside Escape – Sleeps 8, Walk to Beach
Scituate
10.0 out of 10, Exceptional, (13 reviews)
"A great location near everything."
United States
Robert
Scituate Seaside Escape – Sleeps 8, Walk to Beach

14. Renovated Beach House Close to Everything, Minutes to Boston

Renovated Beach House Close to Everything, Minutes to Boston
Quincy
9.2 out of 10, Wonderful, (124 reviews)
"Overall great stay, loved the location"
United States
Anthony E.
The price is AU$621
includes taxes & fees
23 Nov - 24 Nov
Renovated Beach House Close to Everything, Minutes to Boston

15. 284 - Cozy House with free huge parking

284 - Cozy House with free huge parking
Quincy
9.6 out of 10, Exceptional, (81 reviews)
"Communication with the host was great! The most important"
United States
Fayette J.
The price is AU$833
includes taxes & fees
26 Oct - 27 Oct
284 - Cozy House with free huge parking

16. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"We had a great visit and the house gave us everything we needed for a comfortable stay. The rooms were nicely furnished and the bedrooms were spacious. The location was convenient for accessing the bus and the subway. The host was very friendly and responsive. We hope to visit again!"
United States
Christina B.
The price is AU$779
includes taxes & fees
4 Nov - 5 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖

17. Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.6 out of 10, Exceptional, (33 reviews)
"We were very pleased with the cleanliness, size of the 2 bedrooms, the kitchenette, bathroom and location! Our Host was very easily contacted and responded quickly always --- we would highly recommend this location as it was easy access to major highways. Will definitely stay again when another function happens! TY Delphine!"
United States
Patricia B.
The price is AU$326
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom apartment with WiFi, AC in superb Canton

18. 60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Mattapan
9.6 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay"
United States
Sybal C.
The price is AU$627
includes taxes & fees
3 Nov - 4 Nov
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

19. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (456 reviews)
"Great price for the place given the location."
United States
Beenish
The price is AU$326
includes taxes & fees
11 Nov - 12 Nov
Maverick Suites at 28 Fenway

20. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (213 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is AU$367
includes taxes & fees
23 Nov - 24 Nov
Global Luxury Suites East Boston
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.
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Top Rockland Hotel Reviews

Find out more about Rockland

Everything you need to know about Rockland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rockland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland holiday rentals we have selected for you start as low as AU$212 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rockland rentals

At Expedia, we put the best Rockland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rockland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Rockland?

Yes, there are holiday rentals in Rockland close to Rockland Ice Rink, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Rockland. Make sure you have time to check out the hockey games and coffee shops during your trip.

What are some of the best holiday rentals that Rockland has to offer?

Boston's Best Vacation Home : This holiday home rental outside of Rockland is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

What can I see and do in Rockland?

Family-friendly attractions include Rockland Ice Rink, whereas Major Reed Park is a spot to enjoy the outdoors. Copley Square and Faneuil Hall Marketplace are other popular places to visit in the area.

What are holiday rentals like in Rockland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rockland. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.