Rockland holiday rentals

We found 315 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Rockland that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Rockland

Showing deals for:29 Jan - 5 Feb

Image gallery for Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Twin bed with trundle bed in second room in Master Bedroom Suite
8.6 out of 10, Excellent, (49 reviews)
Excellent
(49 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
Price is AU$2,612
for 7 nights, 1 room
AU$373 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

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The friendly area of Rockland awaits your stay

Learn about the unique charm of Rockland with a stay in a holiday home rental. Travellers to this welcoming city praise the shopping, restaurants and ice skating. Boston Convention and Exhibition Center and Copley Square are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Rockland

Do you want to find attractions to visit in the city? Venture out of your cosy holiday rental and check out everything that makes Rockland a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Rockland Ice Rink (1.6 mi / 2.5 km)
  • Blue Hills Reservation (10.2 mi / 16.4 km)
  • Granite Links Golf Club (10.3 mi / 16.6 km)
  • Blue Hills Ski Area (11.8 mi / 19 km)
  • The Skating Club of Boston (14 mi / 22.6 km)
  • Franklin Park Zoo (15 mi / 24.1 km)

Exploring the natural landscape of Rockland

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Rockland is a great place to get outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (17.3 mi / 27.8 km)
  • Copley Square (17.2 mi / 27.7 km)
  • Nantasket Beach (10 mi / 16.1 km)
  • Minot Beach (11 mi / 17.7 km)
  • Wollaston Beach (11.3 mi / 18.2 km)
  • Duxbury Beach Park (14.9 mi / 24 km)

Transport to and around Rockland

The nearest airport is in Norwood, MA (OWD-Norwood Memorial), located 13.9 mi (22.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 16.9 mi (27.2 km) away.

Frequently asked questions

What is the best area to stay in Rockland when booking a holiday rental?
When considering a holiday rental in Rockland, Massachusetts, a popular area to stay is the vicinity around the town centre. This area offers a charming blend of convenience and local charm, making it an attractive choice for visitors. While the number of properties can vary, you can typically find a good selection of rentals that cater to different preferences and budgets.

Staying near the town centre places you within easy reach of some delightful attractions. For instance, the Rockland Memorial Library is a lovely spot to explore, featuring a rich collection of books and a serene atmosphere. Additionally, the town is close to a range of parks and outdoor spaces, such as the picturesque Rockland Golf Course, which is great for those who enjoy a round of golf or simply want to take in the scenic views.

Moreover, the area boasts several local eateries and shops, allowing guests to experience the community's hospitality and unique offerings.
When is the best time to visit Rockland for a holiday rental?
The peak season for holiday rentals in Rockland, Massachusetts, is from May to July, with July being the most popular month among visitors. This vibrant period attracts those seeking seaside fun, with plenty of outdoor activities such as beach outings, boating, and exploring local parks. The warm summer weather, typically ranging from 15 to 30 degrees Celsius, provides a comfortable climate for enjoying Rockland's beautiful coastline and engaging in various recreational pursuits.

During this peak time, the town buzzes with activity, making it an ideal choice for families and adventure-seekers alike. You can take advantage of the lively option by visiting local festivals, seafood restaurants, and art galleries, all while soaking up the sun.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this month is considered the low season, it offers a unique charm with festive decorations and a quieter ambience, superb for those who prefer a more relaxed getaway. The holiday spirit in Rockland can be quite enchanting, with opportunities for cosy indoor activities and enjoying the local community's festive events.

Ultimately, your choice of when to visit Rockland will depend on your preferences for lively summer adventures or a peaceful winter retreat filled with seasonal charm.
What are the top attractions in Rockland?
In Rockland, Massachusetts, visitors can explore a variety of attractions that highlight the area's charm and local culture. The downtown area offers a selection of quaint shops and restaurants, great for those looking to experience local cuisine and shopping. The Rockland Memorial Library is a lovely spot for book lovers and hosts community events throughout the year.

For outdoor enthusiasts, the nearby Rockland Golf Course provides a scenic setting for a round of golf, while the picturesque Hingham Bay is not far away, offering opportunities for boating and fishing. The historic site of the Old Ship Church, located in nearby Hingham, is also worth a visit, as it is one of the oldest meetinghouses in the United States.

Families can enjoy a day at the nearby South Shore Plaza, which features shopping and dining options, or take a short drive to Wompatuck State Park for hiking and picnicking.
Are all fees included in the Rockland holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Rockland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Rockland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Rockland holiday homes?
You can find great discounts on holiday homes in Rockland on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Rockland holiday home booking on Stayz?
To find Rockland holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Rockland?
A long-stay holiday home in Rockland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Rockland holiday home?
Book your Rockland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Rockland?
Prices for holiday homes in Rockland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Rockland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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