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Rockland Holiday Rentals

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Our top choices for Rockland holiday rentals

1. Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield

Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield
Marshfield
10.0 out of 10, Exceptional, (27 reviews)
""The Cozy Cottage" is exactly as the name implies. Lovely, cozy cottage steps from the beach in a quiet neighborhood setting. Wonderful time there."
United States
merrie o.
The price is NZ$700
includes taxes & fees
27 Sept - 28 Sept
Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield

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, (52 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 NZ$667
includes taxes & fees
27 Sept - 28 Sept
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

3. Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
Duxbury
10.0 out of 10, Exceptional, (35 reviews)
"Excellent place, we will be returning. "
United States
Kevan
The price is NZ$743
includes taxes & fees
4 Oct - 5 Oct
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

4. Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (125 reviews)
"Great location, clean and the room setup is perfect for family."
United States
Heather
The price is NZ$757
includes taxes & fees
28 Sept - 29 Sept
Thomas Sea Suites

5. Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
9.8 out of 10, Exceptional, (60 reviews)
"Second time staying at this beautiful Cohasset destination and home. Would love to come back again. Excellent location, harbor walks, downtown walks, comfortable beds, well appointed kitchen, everything you need!"
United States
Beth G.
The price is NZ$1,198
includes taxes & fees
28 Sept - 29 Sept
Village Colonial / Harbor Views.

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, (33 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is NZ$637
includes taxes & fees
29 Sept - 30 Sept
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

7. 284 - Cozy House with free huge parking

284 - Cozy House with free huge parking
Quincy
9.8 out of 10, Exceptional, (80 reviews)
"Nice quiet street perfect for families and close to Boston."
United States
Alisa O.
The price is NZ$843
includes taxes & fees
27 Sept - 28 Sept
284 - Cozy House with free huge parking

8. 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 NZ$585
includes taxes & fees
27 Sept - 28 Sept
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

9. 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, (56 reviews)
"Great overall stay!"
United States
Chris R.
The price is NZ$876
includes taxes & fees
28 Sept - 29 Sept
Cozy three-bedroom home close to Boston w/ plenty of parking

10. 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, (38 reviews)
"Great, spacious property for a family stay & clear communication with host. "
United States
Amber M.
The price is NZ$905
includes taxes & fees
29 Sept - 30 Sept
Spacious 6BR Quincy Beach Near Boston | Family Vacation & Pet-Friendly 555

11. 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, (30 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is NZ$397
includes taxes & fees
27 Sept - 28 Sept
Charming 2-bedroom apartment with WiFi, AC in superb Canton

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

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (90 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 NZ$605
includes taxes & fees
5 Oct - 6 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖

13. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (481 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is NZ$376
includes taxes & fees
28 Sept - 29 Sept
Temple Place Suites

14. New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602

New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602
Mattapan
9.4 out of 10, Exceptional, (28 reviews)
"Fantastic experience! Clean and tidy upon arrival! Great communication and excellent to work with! We loved the location and would book again if we ever return to Boston! "
United States
Jessica D.
The price is NZ$650
includes taxes & fees
28 Sept - 29 Sept
New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602

15. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.6 out of 10, Excellent, (15 reviews)
"Didn’t feel it was cleaned the best. Good location for Fenway Park"
United States
Dawn B.
The price is NZ$450
includes taxes & fees
20 Oct - 21 Oct
Stunning Back Bay Studio Apartment

16. 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 NZ$409
includes taxes & fees
30 Sept - 1 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

17. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (346 reviews)
"Location is great"
United States
Eria
The price is NZ$335
includes taxes & fees
28 Sept - 29 Sept
Premier Suites - Bay Village

18. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (124 reviews)
"Lovely full apartment with a great location. Our host was highly responsive, the property was clean, quiet, and perfectly well appointed. This is a perfect location to catch the T and explore all of Boston from."
United States
Elizabeth F.
The price is NZ$808
includes taxes & fees
30 Sept - 1 Oct
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

19. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is NZ$570
includes taxes & fees
28 Sept - 29 Sept
Bright 2BR by Boston Waterfront

20. 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 NZ$1,511
includes taxes & fees
20 Oct - 21 Oct
4BR 6BEDS WOLLASTON BEACH. NearBOSTON3
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rockland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Rockland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Rockland. Seeing all the best attractions is bound to make you fall in love with Rockland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Rockland short-term rentals, that won’t be hard to do.

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?

Cozy 3BD 1BA near Beach T-10 Min from Boston: This holiday home rental outside of Rockland is equipped with a patio, a Smart TV and WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 Boston Harbor 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.