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

Rockland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Rockland vacation rentals

A neatly arranged bedroom with a bed, bedside tables, a dresser, and a window providing natural light.

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.
$405 nightly
The price is $452
Nov 2 - Nov 3
Total with taxes and fees
Cozy three-bedroom home close to Boston w/ plenty of parking
A wooden front door with a glass panel and the number 383.

2. 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, (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.
$403 nightly
The price is $450
Oct 26 - Oct 27
Total with taxes and fees
FREE Parking & Bright 3BR Boston Townhouse Near Transit • Pet-Friendly - 383
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

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.
$250 nightly
The price is $279
Nov 1 - Nov 2
Total with taxes and fees
Charming 3-Beds In 2-bedrooms Apartment Near Quincy Adams
A hotel room with two beds, a TV, a nightstand, a lamp, and a window with curtains.

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
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

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.
$392 nightly
The price is $438
Nov 1 - Nov 2
Total with taxes and fees
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

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, (677 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
$357 nightly
The price is $410
Nov 11 - Nov 12
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
A kitchen with white cabinets, a tiled backsplash, and a knife block on the counter.

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.
$392 nightly
The price is $438
Nov 1 - Nov 2
Total with taxes and fees
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area set for six with a marble table.

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.
$555 nightly
The price is $619
Oct 26 - Oct 27
Total with taxes and fees
Spacious 6BR Quincy Beach Near Boston • Family Vacation & Pet-Friendly 555
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

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
$270 nightly
The price is $297
Nov 9 - Nov 10
Total with taxes and fees
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

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
$246 nightly
The price is $283
Nov 1 - Nov 2
Total with taxes and fees
The Chester Hotel
A spacious living room with a large white marble table, a blue sofa, and a view of the street through large windows.

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
$337 nightly
The price is $376
Oct 25 - Oct 26
Total with taxes and fees
Thomas Sea Suites
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

12. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (766 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
$293 nightly
The price is $336
Nov 8 - Nov 9
Total with taxes and fees
Global Luxury Suites Downtown Boston
A spacious living room with a large sectional sofa, a striped armchair, and a wooden coffee table with snacks. A staircase with a white railing leads to an upper level.

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
$570 nightly
The price is $625
Oct 22 - Oct 23
Total with taxes and fees
Scituate Seaside Escape – Sleeps 8, Walk to Beach
A view of a beach with cars parked on the side of the road, a pedestrian crossing, and a wooden fence.

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.
$408 nightly
The price is $455
Oct 22 - Oct 23
Total with taxes and fees
Renovated Beach House Close to Everything, Minutes to Boston
A spacious living room with a grey sofa, wooden flooring, a flat-screen TV, and a staircase.

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

Entire 5BR Large Family House near Perry Beach • Pet-Friendly w/Parking 284
Quincy
9.6 out of 10, Exceptional, (81 reviews)
"Communication with the host was great! The most important"
United States
Fayette J.
$545 nightly
The price is $608
Oct 26 - Oct 27
Total with taxes and fees
Entire 5BR Large Family House near Perry Beach • Pet-Friendly w/Parking 284
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

16. 🎖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.
$490 nightly
The price is $563
Nov 4 - Nov 5
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A two-story house with a gabled roof, multiple windows, and a front porch.

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.
$202 nightly
The price is $226
Oct 25 - Oct 26
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in superb Canton
A modern kitchen with a large island, white cabinets, and pendant lighting.

18. Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603

Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603
Mattapan
9.6 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay"
United States
Sybal C.
$392 nightly
The price is $450
Nov 3 - Nov 4
Total with taxes and fees
Family-Friendly 3BR Apt - Easy Downtown Boston Accesss - near Franklin Park 603
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

19. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (455 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
$234 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

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
$273 nightly
The price is $314
Nov 11 - Nov 12
Total with taxes and fees
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Definitely deserved that 5 stars. Room decor, the view was outstanding."
John 1-night trip
Posted less than an hour ago
Encore Boston Harbor

Find out more about Rockland

Everything you need to know about Rockland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rockland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rockland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rockland rentals

At Expedia, we put the best Rockland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.