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Rockland vacation rentals

We found 272 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Rockland that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the amenities you need and want, such as air conditioning and a TV. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Rockland

Showing deals for:Sep 12 - Sep 19
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Find out more about Rockland

Find out more about Rockland

Why visit Rockland

  1. Outdoor Adventures: Enjoy a variety of outdoor activities, from visiting local parks to relaxing on beautiful beaches.
  2. Charming Market Street: Explore the vibrant heart of Rockland, filled with cozy homes and local shops.
  3. Historic Homes: Discover the town's charm through its historic houses that reflect its rich heritage.
  4. Family-Friendly Attractions: Engage in numerous attractions suitable for all ages, making it perfect for family outings.
  5. Diverse Accommodation: Choose from cozy apartments, spacious homes, and modern condos to suit your vacation needs.

Popular types of accommodation in Rockland

Planning a getaway to Rockland? You've come to the right place! Our vacation rentals offer a variety of options to suit your needs, including apartments, condos, and houses. Whether you're looking for Rockland homes for rent or charming townhouses, we provide transparent information to help you find the perfect place to stay. Enjoy your vacation with confidence, knowing you have the best rental options at your fingertips!

  • Apartments: The top choice for visitors in Rockland, offering modern amenities and convenience for both short and long stays.
  • Condos: A popular second option, providing a blend of privacy and community, ideal for families or groups.
  • Houses: These homes offer a unique, home-like experience, perfect for those seeking space and comfort.
  • Cottages: A charming option that provides a cozy atmosphere, perfect for a romantic getaway.
  • House Boats: For a unique experience, house boats offer an adventurous stay on the water.**

Top attractions in Rockland

Rockland, Massachusetts, offers a delightful mix of outdoor activities and family-friendly attractions. Visitors can explore beautiful beaches, historic college campuses, and charming houses. Whether you're seeking cultural experiences or outdoor adventures, Rockland caters to all types of travelers. Don’t forget to request local tours to enhance your visit and take the time to view the historic homes that add to the town's charm.

  1. Fenway Park: A historic sports stadium, Fenway Park is a must-see for baseball fans, showcasing the rich culture and sports vibes of Boston. Experience the excitement of a Red Sox game in this iconic venue located 18 miles away from Rockland.
  2. TD Garden: This premier event venue, also 18 miles from Rockland, hosts everything from sports games to concerts, offering a vibrant atmosphere perfect for business and entertainment.
  3. Boston Common: Located 17 miles away, this urban park is a beautiful retreat for families and outdoor enthusiasts, featuring lush landscapes and city vibes, perfect for a relaxing day out.

Things to do recommended for couples

Looking for a romantic getaway in Rockland? Enjoy a lively night at the House of Blues Boston, just 18 miles away, or hit the slopes at Blue Hills Ski Area, 12 miles from town. For a touch of luxury, unwind at the Marshfield Country Club, only 11 miles away.

Things to do recommended for families

Your family will love visiting Gillette Stadium for a thrilling sports experience, ice skating at the Rockland Ice Rink for fun and adventure, and unwinding at Two Mile Farm for some relaxation and wellness. Enjoy a memorable vacation filled with activities for everyone!

Things to do recommended for groups

Experience the vibrant atmosphere of Faneuil Hall Marketplace, just 17 miles away for shopping and entertainment. Enjoy a round of golf at Rockland Golf Course or unleash your adrenaline at F1 Boston, located 9 miles away, with thrilling motor racing for your group.

What do I need to keep in mind when booking a vacation in Rockland

When traveling with a group, family, pets, or planning extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Rockland with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these features and more on Vrbo.
  • Traveling to Rockland with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Rockland: For many families, a vacation wouldn’t feel complete without their furry companions. If that resonates with you, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Rockland: If you’re in search of vacation rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Rockland

Rockland, Massachusetts, offers a delightful blend of outdoor adventures and family-friendly attractions. Explore the charming Market Street, the vibrant heart of Rockland, and discover the cozy homes that capture the town's essence. Nearby cities provide a friendly atmosphere, perfect for romantic getaways or urban excursions. Whether you're enjoying the local parks or savoring delicious cuisine, Rockland promises a memorable vacation experience for every traveler.

  • Abington: Located a mere 2 miles from Rockland, Abington offers a delightful mix of outdoor adventures and family-friendly activities. This vibrant city is perfect for a day of shopping at its local mall or enjoying a round of golf at nearby courses. Nature enthusiasts will appreciate the close proximity to beautiful beaches, ideal for a family day out, as well as a local stadium that often hosts community events. Whether you're looking to relax or engage in recreational activities, Abington has something to offer every traveler.
  • South Weymouth: Just 3 miles from Rockland, South Weymouth is a bustling city that caters to both business travelers and families seeking leisure. Visitors can enjoy exciting music concerts or try their luck at the local casino, while the nearby resort offers a perfect escape for relaxation. The area's beautiful beaches and family-friendly stadium provide ample opportunities for fun and recreation. South Weymouth is a lively destination that balances work and play, making it an excellent spot for a day of exploration.
  • Whitman: A charming city located 4 miles from Rockland, Whitman is a great destination for those interested in outdoor activities, family experiences, and city life. This vibrant community features various music concerts and educational venues that engage visitors of all ages. Shopping enthusiasts will find plenty of options at the local shopping center. With easy access to stunning beaches and family-friendly stadiums, Whitman offers a well-rounded experience, perfect for a memorable day trip.

Best time to go to Rockland

If you're planning a trip to Rockland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.2°F (-1.0°C)Light RainMostly SunnySlightly LowSlightly Low
February31.5°F (-0.3°C)Light RainMostly SunnyAverageSlightly Low
March37.6°F (3.1°C)Light RainMostly SunnySlightly HighAverage
April47.7°F (8.7°C)Light RainMostly SunnyAverageAverage
May57.6°F (14.2°C)Light RainMostly SunnyAverageSlightly High
June65.3°F (18.5°C)Light RainMostly SunnySlightly HighAverage
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
August71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October55.4°F (13.0°C)Light RainMostly SunnyAverageSlightly High
November44.6°F (7.0°C)Light RainMostly SunnySlightly LowAverage
December36.5°F (2.5°C)Light RainMostly SunnySlightly LowSlightly Low

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your reservation. Being the planner truly has its benefits! By enrolling in our travel rewards program, OneKey, you'll gain immediate access to member discounts and the opportunity to earn and redeem OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are neatly organized into categories such as Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The friendly area of Rockland awaits your stay

Experience the unique character of Rockland with a stay in a vacation home rental. Travelers to this welcoming city praise the shopping, restaurants and ice skating. Copley Square and Flynn Cruiseport Boston are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Rockland

Are you hoping to discover things to do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Rockland a one-of-a-kind vacation spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (17.2 mi / 27.7 km)
  • Rockland Golf Course (0.5 mi / 0.8 km)
  • Rockland Ice Rink (1.6 mi / 2.5 km)
  • Campanelli Stadium (7.7 mi / 12.4 km)
  • F1 Boston (8.8 mi / 14.2 km)
  • Blue Hills Reservation (10.2 mi / 16.4 km)

Exploring the natural landscape of Rockland

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Rockland is a great place to spend some time outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Copley Square (17.2 mi / 27.7 km)
  • Boston Common (17.3 mi / 27.8 km)
  • Adams National Historic Park (9.9 mi / 16 km)
  • Nantasket Beach (10 mi / 16.1 km)
  • Nantasket Beach Reservation (10.2 mi / 16.5 km)
  • Peggoty Beach (10.9 mi / 17.5 km)

Transportation to and around Rockland

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

Frequently asked questions

How much does it cost to rent a vacation rental in Rockland?
Different things affect what you’ll pay for a vacation rental in Rockland, including the length of stay, type of property and season. Still, all Vrbo homes have something in common — amazing value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Rockland?
Prices for beach houses in Rockland can differ depending on the size and style of the property and time of year you’re traveling. Simply enter your dates of travel into Vrbo and the number of guests to see available options and prices. From there you can use our filters to tailor your search results by amenities, ratings, nearby activities and more.
What are the top attractions for families in Rockland?
Give the kiddos a day out at these cool family-friendly attractions in Rockland:

  • Rockland Ice Rink
  • Rockland Golf Course

How old do you have to be to rent a vacation rental in Rockland?
The minimum required age is generally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen Rockland stay before booking your stay.
How long can I rent a vacation rental in Rockland for?
It’s up to the Rockland property. To browse available options offering extended stays, just enter your dates and guest number into Vrbo’s search page. You can enjoy having the entire place to yourself, along with amenities such as a kitchen, air conditioning and a yard where the kids can run around and play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Rockland?
Overnight trip or extended escape, Vrbo has some bargain deals and special discounts in Rockland to suit your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what’s just been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the perfect place to stay — without spending a fortune.

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