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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, (58 reviews)
"Great overall stay!"
United States
Chris R.
The price is £339
includes taxes & fees
18 Oct - 19 Oct
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)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
The price is £299
includes taxes & fees
12 Oct - 13 Oct
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

3. 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, (54 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is £276
includes taxes & fees
13 Oct - 14 Oct
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

4. Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Randolph
10.0 out of 10, Exceptional, (7 reviews)
"Great stay! Host was very responsive to any questions. Family friendly house with lots of beds and a wide open living room. Easy check in and check out process. Nice central location to all that the Boston area has to offer."
United States
Anonymous traveller
The price is £387
includes taxes & fees
12 Oct - 13 Oct
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

5. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (95 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is £252
includes taxes & fees
18 Oct - 19 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖

6. 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, (34 reviews)
"Our experience was excellent! The property was very clean, comfortable, and the accommodations were exactly as represented on the app. The property owner provided excellent instructions for our stay including entry, parking, and departure. We had one question upon arrival and the owner was immediately responsive. We would definitely stay again!"
United States
Kasey F.
The price is £287
includes taxes & fees
13 Oct - 14 Oct
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

7. 74R/2 New renovated Apartment

74R/2 New renovated Apartment
North Quincy
9.2 out of 10, Wonderful, (23 reviews)
"Very lovely stay. Clean space, easy to get in and out of."
United States
Terry T.
The price is £228
includes taxes & fees
12 Oct - 13 Oct
74R/2 New renovated Apartment

8. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is £177
includes taxes & fees
28 Oct - 29 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

9. 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 £436
includes taxes & fees
13 Oct - 14 Oct
Spacious 6BR Quincy Beach Near Boston | Family Vacation & Pet-Friendly 555

10. Spectacular Ocean Sunsets I Pet Friendly

Spectacular Ocean Sunsets I Pet Friendly
Weymouth
8.6 out of 10, Excellent, (4 reviews)
"Location - excellent"
United States
Andrea
The price is £482
includes taxes & fees
12 Oct - 13 Oct
Spectacular Ocean Sunsets I Pet Friendly

11. Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
9.8 out of 10, Exceptional, (60 reviews)
"This was the perfect stay for our family as we celebrated a wedding at the Red Lion Inn!!! It made everything so easy!"
United States
Kelly C.
The price is £525
includes taxes & fees
19 Oct - 20 Oct
Village Colonial / Harbor Views.

12. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (329 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
The price is £235
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway

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

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"Is a great place"
United States
Ramon G.
The price is £435
includes taxes & fees
4 Nov - 5 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖

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

Renovated Beach House Close to Everything, Minutes to Boston
Quincy
9.4 out of 10, Exceptional, (123 reviews)
"Overall great stay, loved the location"
United States
Anthony E.
The price is £385
includes taxes & fees
13 Oct - 14 Oct
Renovated Beach House Close to Everything, Minutes to Boston

15. 74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy

74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy
North Quincy
9.0 out of 10, Wonderful, (6 reviews)
"The host was so responsive to my questions and concerns throughout our stay. We really enjoyed our stay. The apartment was clean, comfortable, and in a great location."
United States
Teresa
The price is £250
includes taxes & fees
1 Nov - 2 Nov
74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy

16. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"The place was exactly as described, it was clean and exactly what we need for our stay."
United States
Jordan C.
The price is £173
includes taxes & fees
9 Nov - 10 Nov
Sleek Studio Apartment in the South End

17. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (33 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is £269
includes taxes & fees
11 Nov - 12 Nov
The Concord Hotel

18. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (364 reviews)
"Convenient location. Comfortable bed."
United States
Kayla
The price is £123
includes taxes & fees
9 Nov - 10 Nov
Premier Suites - Bay Village

19. 4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

4BR 6BEDS WOLLASTON BEACH. NearBOSTON3
Quincy
10.0 out of 10, Exceptional, (46 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.
The price is £625
includes taxes & fees
20 Oct - 21 Oct
4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

20. 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 £494
includes taxes & fees
19 Oct - 20 Oct
284 - Cozy House with free huge parking
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, apart-hotels, 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 favorite 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 depends 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 £123 per night. Entering your travel dates in the search wizard you might find 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.