Family-friendly holiday 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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Guest favourite

Guesthouse in South Bristol

4.98 out of 5 average rating, 378 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Guest favourite

Home in Rockland

4.92 out of 5 average rating, 186 reviews

Rockland Relaxing Retreat/Walk to Town (STR24-16)

Come enjoy the natural beauty of Coastal Maine as well as lobster, art, and wine in Rockland, Maine. Stroll to Rockland’s restaurants, bakeries, shops, museums, breweries, and ferry terminal from this comfortable 3-bedroom, 1.5 bath house. The house has 1 King bed, 1 Queen bed, and 1 twin/trundle bed. It is kid-friendly with a large back yard and a fully-equipped kitchen and smart TV, (but no cable and no AC), and PS3 with games. Camden is nearby and has a ski resort. 10% military discount.

Guest favourite

Home in Rockland

4.98 out of 5 average rating, 107 reviews

Charming, Family-Friendly Historical In Town Home

STR24-11 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer. Ask us about free delivery from Ruckus Donuts!

Guest favourite

Home in Rockland

4.95 out of 5 average rating, 356 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!

Guest favourite

Home in Rockland

4.93 out of 5 average rating, 141 reviews

Perfect Family & Friends Vacation for 10+ STR20-32

Welcome to Summer in Maine! Blues Festival July 13th-14th, Lobster Festival July 31-Aug 4th, Union FairJuly 7th-10th, The Common Ground Fair Sept 20th-22nd and more...See the Islands by ferry. Shop in the historic Main Street. Great food from casual to elegant.Explore the Midcoast. Our house will sleep 8 -10 Adults (under 5 don't count). Big dining table for the family. Kitchen stocked. A downstairs bedroom and ADA bathroom. Backyard wGrill and Picnic Table w/Umbrella. See All Our Photos.👍

Guest favourite

Rental unit in Edgecomb

4.91 out of 5 average rating, 322 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Guest favourite

Guest suite in Rockport

4.92 out of 5 average rating, 221 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.

Guest favourite

Rental unit in Belfast

4.96 out of 5 average rating, 361 reviews

Belfast Harbor Loft

Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Guest favourite

Cottage in Owls Head

4.99 out of 5 average rating, 160 reviews

Coastal Maine contemporary cottage

Our cottage is meant to be both contemporary and rustic. It is where we go to get away from the hustle and bustle of the modern world and slow down. There is no TV or internet, even our phone is an old rotary one. You will see that we have a good radio, and games and books to read, and plenty of things to do outside. We hope you will take the time at our cottage to comfortably reconnect with yourself, and each other, while enjoying what Maine is renowned for, our quality of life.

Guest favourite

Cottage in Belfast

4.99 out of 5 average rating, 122 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Guest favourite

Guesthouse in Rockland

4.88 out of 5 average rating, 359 reviews

Sweet Willow Suite, Rockland, private 1st floor

Quiet and private 1-bdrm apartment, 1st floor, 1-story building. Light-filled open area, queen bed, full bath with walk-in shower. Located 1.5 blocks from Main St. Easy walk to downtown and harbor. Suite includes many safety features. Host is hands-on, will greet you at check-in, then respect your privacy. If you are looking for a totally anonymous experience, this is not it. Licensed with the City of Rockland #STR24-7.

Guest favourite

Guesthouse in Camden

4.92 out of 5 average rating, 239 reviews

Superb Location w/EV Hk up & Walk to town & ocean

Our cozy cottage sits in a quiet family friendly neighborhood known for its charm. Its just a short walk to Laite Beach, to town, restaurants and the YMCA. It comfortably accommodates a small family. Very pet friendly. Crib is available. Electric Car hook up too...