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

Rockland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rockland vacation rentals

1. 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 CA $462
CA $580 total
includes taxes & fees
Oct 3 - Oct 4
Thomas Sea Suites

2. 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
9.8 out of 10, Exceptional, (28 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 CA $404
CA $568 total
includes taxes & fees
Oct 2 - Oct 3
Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield

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 CA $354
CA $599 total
includes taxes & fees
Oct 11 - Oct 12
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

4. 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 CA $424
CA $972 total
includes taxes & fees
Oct 5 - Oct 6
Village Colonial / Harbor Views.

5. 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 CA $338
CA $721 total
includes taxes & fees
Oct 6 - Oct 7
Cozy three-bedroom home close to Boston w/ plenty of parking

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (668 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is CA $793
CA $912 total
includes taxes & fees
Oct 4 - Oct 5
Marriott Vacation Club® at Custom House, Boston

7. FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

FREE Parking & Bright 3BR Boston Townhouse Near Transit • 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 CA $256
CA $564 total
includes taxes & fees
Oct 5 - Oct 6
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383

8. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (324 reviews)
"Room was clean, neat area."
United States
Keir
The price is CA $196
CA $346 total
includes taxes & fees
Oct 1 - Oct 2
Maverick Suites at 89 Marion

9. 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 CA $493
CA $903 total
includes taxes & fees
Oct 5 - Oct 6
Spectacular Ocean Sunsets I Pet Friendly

10. 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 CA $317
CA $641 total
includes taxes & fees
Oct 13 - Oct 14
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

11. 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 CA $485
CA $1,234 total
includes taxes & fees
Oct 21 - Oct 22
4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

12. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (754 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is CA $455
CA $699 total
includes taxes & fees
Oct 26 - Oct 27
Global Luxury Suites Downtown Boston

13. 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 CA $195
CA $483 total
includes taxes & fees
Oct 1 - Oct 2
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

14. 🎖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 Ashmont Apartment - Close to Subway & Downtown Boston🎖

15. Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
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 CA $209
CA $681 total
includes taxes & fees
Oct 1 - Oct 2
Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

16. 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 CA $317
CA $818 total
includes taxes & fees
Oct 4 - Oct 5
Spacious 6BR Quincy Beach Near Boston • Family Vacation & Pet-Friendly 555

17. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (206 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is CA $280
CA $453 total
includes taxes & fees
Oct 15 - Oct 16
Maverick Suites at 245 Newbury St

18. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (322 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is CA $293
CA $483 total
includes taxes & fees
Oct 1 - Oct 2
Kasa Boston at Fenway

19. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (25 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
The price is CA $338
CA $568 total
includes taxes & fees
Oct 1 - Oct 2
The Concord Hotel

20. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (150 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is CA $267
CA $437 total
includes taxes & fees
Oct 4 - Oct 5
Maverick Suites at 40 Temple St
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Rockland Hotel Reviews

Find out more about Rockland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Rockland?

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

What are some of the best vacation rentals in Rockland?

Boston's Best Vacation Home : Visitors like this Rockland vacation home rental. It 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 vacation rentals like in Rockland?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Rockland. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for families.