Rockland Vacation Rentals from $205: Search Short-Term Rentals

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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

North Braintree

Chris R.

$450 nightly

Oct 6 - Oct 7

Total with taxes and fees

A wooden front door with a glass panel and the number 383.

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

Quincy

Alicia R.

$351 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

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

Quincy

Jeff L.

$373 nightly

Oct 13 - Oct 14

Total with taxes and fees

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

Quincy

Sheldon S.

$373 nightly

Oct 13 - Oct 14

Total with taxes and fees

A spacious living room with a grey sofa, wooden flooring, a flat-screen TV, and a staircase.

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

Quincy

Alisa O.

$475 nightly

Oct 7 - Oct 8

Total with taxes and fees

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area set for six with a marble table.

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

Quincy

Amber M.

$489 nightly

Oct 4 - Oct 5

Total with taxes and fees

An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

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

Dorchester

Katie C.

$311 nightly

Oct 5 - Oct 6

Total with taxes and fees

A spacious living room with a large window overlooking a body of water, a dining area with a view, and a cozy seating arrangement.

8. Spectacular Ocean Sunsets I Pet Friendly

Weymouth

Andrea

$569 nightly

Oct 5 - Oct 6

Total with taxes and fees

A living room with a sofa, coffee table, and a view of the kitchen.

9. Village Colonial / Harbor Views.

Cohasset

Beth G.

$623 nightly

Oct 4 - Oct 5

Total with taxes and fees

A two-story house with a gabled roof, multiple windows, and a front porch.

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

Canton

Stephanie G.

$202 nightly

Oct 7 - Oct 8

Total with taxes and fees

A gazebo with a stone barbecue grill and a table with chairs.

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

Dedham

Cortney

$207 nightly

Oct 28 - Oct 29

Total with taxes and fees

A rooftop dining area with outdoor seating, a view of the cityscape, and a modern building with large windows.

12. 4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

Quincy

Jennifer V.

$745 nightly

Oct 20 - Oct 21

Total with taxes and fees

A modern kitchen with a large island, white cabinets, and pendant lighting.

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

Mattapan

Nicole M.

$325 nightly

Oct 4 - Oct 5

Total with taxes and fees

A spacious living room with a grey sofa set, a coffee table, and a ceiling fan. Large windows provide a view of the cityscape.

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

Duxbury

Kevan

$400 nightly

Oct 4 - Oct 5

Total with taxes and fees

15. Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Dedham

Julien Alfred Joseph

$237 nightly

Oct 4 - Oct 5

Total with taxes and fees

A residential property with a wooden staircase leading to a deck, surrounded by a fenced yard with a large tree and a small house in the background.

16. Downtown!! Located in the Cultural District - One Block to Yacht Club

Plymouth Cultural District

William W.

$328 nightly

Oct 22 - Oct 23

Total with taxes and fees

A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

17. Light-filled Studio | Back Bay

Back Bay

Adina S.

$251 nightly

Oct 29 - Oct 30

Total with taxes and fees

A modern living room with a flat-screen TV, a white sofa, a coffee table, and decorative items.

18. Lorenzo Inn

Dorchester

patrick

$335 nightly

Oct 4 - Oct 5

Total with taxes and fees

A cozy living room with a sofa, chairs, a TV, and a dining area with a table and chairs.

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

Marshfield

merrie o.

$389 nightly

Oct 2 - Oct 3

Total with taxes and fees

A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

20. The Chester Hotel

South End

Shanida

$324 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Rockland Hotel Reviews

Arcadian Hotel

10/10 Excellent

"Friendly staff"

The Revolution Hotel

8/10 Good

"The hotel itself is very nice, and the staff were all lovely. I was admittedly disappointed with my room, as I had booked a room with a bath inside, and according to the images on the website, I thought I’d have a glass shower and robe. However, the bathroom was more like a college dorm, with just a curtain that didn’t keep the water from flooding the bathroom. The toilet didn’t have a lid. It was also a step up to the bathroom, which could be precarious when it was wet. The bed was comfy, but there were no drawers for storing clothes. Overall, I was here for only a few days, so it was fine, but it just wasn’t what I thought based on the website."

citizenM Boston North Station

8/10 Good

"Unexpected. Liked the open lounge living room concept with couches, TV, board games and a coffee/drink bar plus a water refill station. Breakfast was delicious. Staff was super nice! Self check-in worked well. Disliked the room-it was too compact-felt like we were in an airstream, long and narrow with bed at end (which was uneven/slanted and made for uncomfortable sleeping) between the 2 walls. No seating other than a bench (used for suitcase) and desk chair right next to the bed. Sink vanity in the open room was narrow, no storage space. Toilet and shower were in a capsule-like space with frosted glass walls and shower door exit/entry. Really odd. Mini iPad for blinds, lights and TV were cool. Thankful we were only in the room 2 nights and not in the room at all during the day due to our plans. Overall adequate, Euro modern - that’s the brand and feel they are going for, but we didn’t expect it."

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 $205 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.

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Things to do in Braintree

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.

Room 1

Check prices for these dates

Our top choices for Rockland vacation rentals

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

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

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

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

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

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

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

8. Spectacular Ocean Sunsets I Pet Friendly

9. Village Colonial / Harbor Views.

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

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

12. 4BR 6BEDS WOLLASTON BEACH. NearBOSTON3

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

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

15. Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

16. Downtown!! Located in the Cultural District - One Block to Yacht Club

17. Light-filled Studio | Back Bay

18. Lorenzo Inn

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

20. The Chester Hotel

Find vacation rentals that suit your style

Top Rockland Hotel Reviews

Arcadian Hotel

The Revolution Hotel

citizenM Boston North Station

Hyatt Regency Boston/Cambridge

Copley Square Hotel, a FOUND Hotel

Encore Boston Harbor

Hilton Boston Park Plaza

The Dagny Boston

Hyatt Regency Boston Harbor

Find out more about Rockland

Explore a world of travel with Expedia

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