Family-friendly vacation rentals in Rockland

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Top-rated family-friendly rentals in Rockland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
The kitchen area features a spacious countertop with dark cabinetry and modern appliances. Bright, sloped ceilings are complemented by large windows that provide abundant natural light. A cozy living area is visible, adorned with comfortable seating and decorative elements that reflect the coastal theme.
Apartment in Owls Head
4.95 out of 5 average rating, 113 reviews

Oceanview Escape near Maine Beaches

Located at the end of a private road you will find the area very peaceful with beautiful ocean view sunrises and sunsets and lots of wildlife sightings. This cozy 1000 square foot apartment has been recently renovated for a clean coastal vibe. The house was originally hand built in 2000 by the owner. You will notice the craftsmanship detail, built ins, hand made furniture and unique nautical style throughout the apartment. The kitchen is fully stocked and equipped with stove, full fridge and a new microwave and dishwasher. The living space provides a 50 inch smart TV and queen pull out sofa. Enjoy the vast ocean views from the large living room picture windows. Watch the boats cruising through Penobscot Channel or a local lobsterman hauling their traps. The bedroom offers a queen bed and plenty of closet/storage space. There is a large jacuzzi tub and separate hand tiled shower in the bathroom. Spacious deck off the kitchen/living area provides an outdoor dining area and grill. Enjoy dinner or drinks taking in the salty ocean air and views. At the base of the entry stairs is a separate patio space with propane fire pit shared amongst both living spaces. Located behind the apartment is an adorable playhouse with slide, saucer swings and a rock climbing wall that is shared amongst the neighborhood. Please play at your own risk. WiFi included

Top guest favorite
The exterior of the tiny house displays a simple structure with light-colored siding and multiple windows. Decorative butterflies adorn the side wall. A gravel pathway leads up to wooden steps, providing access to the entrance. Green grass surrounds the house, contributing to the serene setting.
Tiny home in Rockland
4.96 out of 5 average rating, 175 reviews

Simplicity-Just what you need! STR24-20

The first legal tiny house in Rockland! All the comforts of home in this sweet tiny house. First floor living, open floor plan. Small but roomy. In walking distance to Main St, South end beach, the Lobster Festival, Blues Festival, Boat Show and more. You will love the simple concept this little gem offers whether just staying the weekend or for weeks. It is quiet and serene as you sit in the living space and have a warm cup of tea or a cold lemonade. We love our tiny house and hope you do too!

Guest favorite
The exterior of a two-story coastal home is presented with light blue siding and white trim. A white picket fence surrounds the front yard, which features green grass and small shrubs. Large windows allow natural light to illuminate the interior spaces.
Home in Rockport
4.92 out of 5 average rating, 149 reviews

Seaside House/Downstairs

Enjoy everything coastal Maine has to offer in this coastal home with great ocean views. The space is light and bright and yet cozy! The house has a well appointed kitchen and is well maintained. You will find everything you need and more in this comfortable seaside retreat. Access to the beach is a short walk away. The house sits across the street from Clam Cove and is not directly on the beach. Beach access is private, quick and easy. There is also a large back yard to play or relax in.

Guest favorite
The exterior of the cottage features a light gray shingle facade, complemented by white trim around the windows and front door. A set of three windows with flower boxes is situated on each side of the door. A welcoming porch leads to the entrance.
Home in Rockland
4.94 out of 5 average rating, 414 reviews

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

Top guest favorite
A bright living area features two modern white chairs and a low coffee table set atop a colorful area rug with floral patterns. Large windows allow natural light to illuminate the space, showcasing a tranquil view of the surrounding greenery.
Guest suite in Rockport
4.91 out of 5 average rating, 244 reviews

Charming Harbor Private One Bedroom

Situated just above a stream just off Rockport Harbor, this quiet, small one-bedroom apartment has its own private entrance and small deck. Located on the back side of RAYR wine and cheese shop, this charming apartment is within a 10-minute walk of two wonderful restaurants in the village of Rockport, 18 Central and Nina June, as well as a lunch spot and a deli. A wonderful getaway space for couples and solo adventurers, you’ll love it because of the location, ambiance, privacy and charm.

Top guest favorite
A charming cottage is situated amidst trees, with a gravel driveway leading to the entrance. A soft sunset is visible in the background, casting gentle hues of pink and purple across the sky, providing a serene backdrop to the peaceful setting.
Guesthouse in Cushing
4.97 out of 5 average rating, 111 reviews

Look! River Run Cottage on tidal salt waterfront

Maine the way life should be is not just an expression at River Run its a way of life. Located in Andrew Wyeth country (town of Cushing, Maine) River Run is a recently renovated 600 square ft cottage 75 ft off the St George river. It sits on 260 feet of privately owned tidal salt water river frontage just miles upriver from the Atlantic Ocean. Great for a romantic get away or to reconnect and recharge. Spend your time on the shore or sight seeing in the near by towns of Rockland and Camden

Top guest favorite
Cabin in Hope
4.98 out of 5 average rating, 367 reviews

Hand built cabin overlooking a pond

Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

Top guest favorite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland
4.98 out of 5 average rating, 491 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

Top guest favorite
Guest suite in Thomaston
4.96 out of 5 average rating, 102 reviews

Studio with Fireplace-Walkable to Downtown

Find peace at this private charming getaway perfect for a couple or a single guest. Stained glass and southern set windows add muted sunlight by day, while the warmth of a fireplace casts a glow by night. The bathroom is perfectly accommodating to the intimate space. A queen size Murphy bed creates comfort for slumber. While an inviting kitchen is equipped with amenities needed to make any chef sigh with relief. Whether for a few days or weeks, stop by to relax and restore.

Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 203 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Top guest favorite
The front of the home features a charming covered porch with red chairs and hanging flower baskets. A light-colored door with glass paneling is centered between two windows. A well-maintained lawn and a slight stone pathway enhance the inviting entrance.
Apartment in Owls Head
4.97 out of 5 average rating, 175 reviews

Coastal Vintage Living

This is a spacious 1000 sq. ft. apartment in my childhood home that has been renovated in Spring 2020 with a modern coastal theme and well appointed with vintage items. We have a well stocked kitchen, cozy dining/living room with a 43" Roku TV, and full laundry. Try a pastry from the professional baker across the road, take a walk down the street to Crockett's Beach, or go for a stroll in downtown Rockland. Remote check-in available.

Top guest favorite
The exterior of the home is illuminated at dusk, showcasing a striking post and beam design. The large deck features outdoor seating, surrounded by lush greenery. Soft lighting enhances the structure's architectural details, creating a welcoming ambiance in a serene natural setting.
Guest suite in Rockland
4.97 out of 5 average rating, 199 reviews

Salty Dog Hilltop Guest Suite (permit #STR26-57)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Popular amenities for Rockland family-friendly rentals

When is the best time to visit Rockland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 694ﺩ.ﺇ 661ﺩ.ﺇ 790ﺩ.ﺇ 731ﺩ.ﺇ 892ﺩ.ﺇ 977ﺩ.ﺇ 1,091ﺩ.ﺇ 1,091ﺩ.ﺇ 948ﺩ.ﺇ 863ﺩ.ﺇ 654ﺩ.ﺇ 720
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Quick stats about vacation rentals that are family-friendly in Rockland

  • Total vacation rentals

    Explore 70 vacation rentals in Rockland

  • Nightly prices starting at

    Rockland vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 3,920 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Rockland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Rockland rentals

  • 4.9 Average rating

    Rockland stays are highly rated by guests—averaging 4.9 out of 5!

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