Family-friendly holiday rentals in Boothbay

4.99 out of 5 average rating, 149 reviews

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

FamilyIndoor spacesBathroom

4.99 out of 5 average rating, 104 reviews

The Happy Harbor House! Walk to town!

The Happy Harbor House - your ultimate harbor retreat! Newly renovated in the coastal design style, located on one level, with all the modern amenities you could hope for. This 3 bedroom 2 bathroom house is an oasis for families, friends or couples looking for a fun & cheerful stay. Although not on the water, you'll be a 2 minute walk to the head of the harbor, Opera House & 3 waterfront restaurants. And a mere 5 minute walk to shops & waterfront attractions in charming Boothbay Harbor.

KitchenIndoor spacesLong stay

Cottage in Boothbay Harbor

The cozy cottage exterior is illuminated in the evening, highlighted by a bright red front door. Soft light glows from the windows, surrounded by lush greenery. A path with wet pavement reflects the light, creating a welcoming entrance amidst the serene wooded surroundings.

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

FamilyIndoor spacesBathroom

4.98 out of 5 average rating, 505 reviews

4.97 out of 5 average rating, 392 reviews

The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.

Cottage in Edgecomb

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

KitchenIndoor spacesAccess

The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.

4.92 out of 5 average rating, 175 reviews

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

KitchenIndoor spacesNearby

A modern kitchen is illuminated by a rustic light fixture with exposed bulbs, enhancing the open layout. Quartz countertops extend through the space, complemented by stainless steel appliances. A vase of mixed flowers sits on the counter, with a scenic view of the ocean visible through large windows.

5.0 out of 5 average rating, 111 reviews

Pinkham Cove - Water Front Cottage

Authentic oceanfront Maine home, with stunning views and amazing sunsets. Located on Pinkham Cove at the mouth of Boothbay Harbor. Experience the village of BBH , hiking trails, Botanical Gardens and explore the tranquility of Maine. This is the perfect getaway cottage. Enjoy the deck and beach access. The home was recently remodeled. The kitchen is a gem with quartz countertops and Bosch appliances. Curl up by the cozy fireplace, enjoy the amazing harbor view!!

FamilyIndoor spacesLong stay

5.0 out of 5 average rating, 135 reviews

The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.

Home in Georgetown

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

FamilyKitchenLocation

4.87 out of 5 average rating, 102 reviews

A lofted sleeping area can be accessed by a wooden ladder within the studio cottage. The interior features warm wood paneling, a cozy seating area with a dark chair, and an open kitchen space fitted with modern appliances. Natural light pours in through large windows.

Tiny home in Edgecomb

Cheerful Cottage with Loft 9

Escape the city to this studio cottage with a sleeping loft in the historic town of Edgecomb Maine. This beautiful 1950s cottage has been restored to all of it's glory with the modern conveniences of today. This cottage along with 13 others sit on five acres of beautiful Coastal Maine for you to explore. You will have scenic views of the beautiful Maine forests and be close to everything in the Boothbay area has to offer.

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 295 reviews

The exterior of a rustic mid-century cabin is framed by lush greenery, featuring a screened-in porch and wooden deck. Stairs lead up to the entrance, and natural stone accents create a seamless blend with the surrounding landscape.

Cabin in Boothbay Harbor

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

FamilyIndoor spacesView

4.96 out of 5 average rating, 195 reviews

A cozy sleeping area includes a queen bed with a grey patterned duvet. A bedside lamp provides soft illumination, and a 'Stay Cozy' pillow enhances the inviting look. Sliding glass doors lead to a deck area, framed by flowing curtains that allow natural light.

Guest suite in Boothbay

Linekin Guest Suite

Tucked away guest studio attached to main home that you will have all to yourself with basic amenities and a sky lighted bathroom. A few minutes to Ocean Point and hiking trails and less than 10 minutes to Boothbay Harbor. **Please note there are stairs that need to be climbed on the front deck in order to access the property. Use the directions provided as your GPS sometimes puts you in a circle around Boothbay!

Indoor spacesFamilyComfort

Cottage in Boothbay Harbor

A serene lakeside view showcases a wooden dock extending into calm waters, framed by lush greenery. Several Adirondack chairs are arranged in a semi-circle on the grass, offering a comfortable space for relaxation and enjoying the natural surroundings.

Adorable Year Round Cottage - Walk to Town!

You will love our waterfront cottage located on Mill Cove in downtown Boothbay Harbor which is a few minute walk to the center of town! Our cottage is a quaint, comfortable home with all the amenities that you could want. Our goal is to ensure that you have a most wonderful vacation. A new heating and air conditioning system guarantees comfort any time of year.

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 115 reviews

4.98 out of 5 average rating, 159 reviews

Home in Georgetown

Cottage on Todd Bay

Autumn is here, and the maples are turning red along the road down from Bath. Days are warm but crisp, and nights are chilly; our guests on Todd Bay have begun building evening fires in the wood stove. We still have a few more available nights in October for fall getaways -- and we're starting to look ahead to May and the 2027 season!

Indoor spacesFamilyBeach

Popular amenities for Boothbay family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 469 reviews

The tree dwelling is elevated among sturdy trees, featuring a wraparound balcony surrounded by foliage. Large windows invite natural light, offering views of the lush surroundings. A rope bridge connects to another elevated structure, enhancing the unique treehouse experience.

Treehouse in Georgetown

Modern Treehouse w/Water Views+Cedar Hot Tub

KitchenFamilySleep quality

4.96 out of 5 average rating, 121 reviews

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

KitchenFamilyComfort

Place to stay in Owls Head

A charming off-grid cabin stands amidst lush greenery, featuring large front windows framed by wooden trim. A picnic table with potted flowers occupies a gravel area in front, inviting outdoor gatherings. Solar panels are visible on the roof, showcasing eco-friendly energy use.

A comforting sweet off grid cabin near the beach!

FamilyIndoor spacesHot tub

4.98 out of 5 average rating, 316 reviews

4.99 out of 5 average rating, 398 reviews

An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.

Tiny home in Freeport

Cozy Rock Cabin #thewaylifeshouldbe

FamilyIndoor spacesBeach

4.9 out of 5 average rating, 179 reviews

A modern A-frame structure is nestled within a wooded setting, featuring a dark exterior with wooden accents. Adjacent, a spacious gazebo is set on a gravel patio, furnished with a dining table and a comfortable seating area, surrounded by trees offering a sense of privacy.

Tiny home in Wiscasset

Tiny A-Frame Romantic Getaway

KitchenIndoor spacesTV

4.91 out of 5 average rating, 149 reviews

Bus in Durham

Solar Powered Bus in Forest | Hot Tub + Wellness

Indoor spacesFamilySleep quality

4.96 out of 5 average rating, 232 reviews

Cabin in West Paris

Log cabin, stunning views, hot tub, fire pit

Indoor spacesFamilyAir conditioning

5.0 out of 5 average rating, 252 reviews

Home in Oxford

The Modern Lakehouse

Indoor spacesKitchenHeating

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 131 reviews

A bright living area features large windows providing views of the ocean and surrounding landscape. Comfortable seating options include a blue sofa and a light-colored couch. A dining table is visible, complemented by wooden beams on the ceiling, enhancing the spacious feel.

Home in Phippsburg

Newly renovated 3BR house w/ stunning ocean views

KitchenFamilyWifi

Superhost

A charming cottage is nestled among trees, showcasing a tranquil setting. Two Adirondack chairs are positioned on the grass, inviting relaxation while offering a view of the water in the distance. A well-maintained garden features vibrant greenery and blooming white flowers.

Cottage in Edgecomb

Spectacular Water View Cottage

FamilyKitchenCheck-in

4.91 out of 5 average rating, 184 reviews

4.95 out of 5 average rating, 121 reviews

A charming cottage is presented with a spacious front porch featuring multiple windows and a balcony above. The exterior showcases a combination of textured siding and stone accents, flanked by a neatly landscaped yard with a rock border.

Cottage in Edgecomb

Sheepscot Harbour Village - 3 Bd Cottage Waterview

KitchenFamilyHeating

4.88 out of 5 average rating, 1026 reviews

The exterior of a charming cottage is captured, featuring rustic wooden shingles. A set of double French doors is framed by greenery and shadows from surrounding trees. A small porch area is visible, leading to a well-maintained lawn.

Cabin in Edgecomb

The Highland Cottage on Sheepscot

KitchenIndoor spacesLong stay

4.79 out of 5 average rating, 135 reviews

Townhouse in Boothbay

Captain Fuller House: Boat Builders Retreat - Main

FamilyIndoor spacesAccess

4.91 out of 5 average rating, 160 reviews

A serene view captures the sunset over the water, with the sun reflecting on the surface. Silhouetted trees are positioned in the foreground, creating a natural frame. The grassy landscape leads towards the water, enhancing the tranquil setting.

Cabin in New Harbor

Rustic Oceanfront Log Cabin

FamilyKitchenLaundry

Superhost

A cozy galley kitchen is presented, featuring wooden cabinetry and appliances, including a refrigerator and dishwasher. A small dining table with two chairs is positioned by a large window, decorated with a vase of flowers. Light streams in, enhancing the warm wood tones.

4.86 out of 5 average rating, 218 reviews

Ocean Harbor Stay

FamilyKitchenGrill

The exterior of a two-story coastal house features a grey facade with white trim. Steps lead to a front door, while large windows offer views of the surrounding greenery. A deck with seating is visible to the right, inviting outdoor relaxation.

4.97 out of 5 average rating, 122 reviews

The Rowe House

FamilyKitchenGetting around

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 251 reviews

A charming exterior of the historic residence showcases a well-maintained garden filled with vibrant purple flowers and greenery. The pale yellow siding of the house complements the octagonal window and green door, offering a welcoming appearance.

Flat in Brunswick

Charming Saltwater Farm apartment

FamilyIndoor spacesComfort

4.96 out of 5 average rating, 182 reviews

A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

KitchenIndoor spacesAir conditioning

4.94 out of 5 average rating, 119 reviews

Home in South Thomaston

Large private area, close to Rockland

Indoor spacesKitchenCheck-in

Home in Old Orchard Beach

OOB Oasis: 6BR Home w/ Private Pool Near Beach

FamilyIndoor spacesAccuracy

4.96 out of 5 average rating, 160 reviews

4.94 out of 5 average rating, 167 reviews

An outdoor pool is surrounded by a patio and bordered by lush greenery and trees displaying autumn colors. The clear water of the pool reflects the overcast sky, and a nearby structure featuring a sloped roof can be seen in the background.

Cabin in West Paris

Cabin on the hill!

KitchenIndoor spacesAir conditioning

4.88 out of 5 average rating, 620 reviews

A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.

Flat in Cape Elizabeth

Portland & Beach & Lighthouses! Romantic! Lovely

Indoor spacesKitchenGetting around

4.93 out of 5 average rating, 147 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in Portland

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Indoor spacesKitchenBiking