Family-friendly holiday rentals in Wiscasset

4.87 out of 5 average rating, 100 reviews

A spacious home is depicted, featuring a neutral exterior with a sloped roof. Lush green trees surround the property, complementing the stone pathway that leads to the entrance. Large windows provide natural light, and manicured shrubs frame the front yard.

Guesthouse in Wiscasset

Private & Peaceful Guest Suite With AC

Welcome to MJ Castle! Imagine waking up to a beautiful sunrise, bird chirping, quiet and peaceful environment. Whether you're traveling through or visiting family in town, this is a perfect place to Stay. Enjoy our guest suite in this beautiful design home. Our guest suite equipped with brand new composite deck, brand new furniture, along with other amenities. This property located on a quiet road right off Route 1, Closed to a boat launch and Downtown Wiscasset. More pictures coming soon!

KitchenIndoor spacesLaundry

4.89 out of 5 average rating, 325 reviews

A charming cottage is nestled among tall trees, featuring a welcoming entrance with wooden doors. A small porch is adorned with a chair, providing a peaceful spot to enjoy the surrounding woodland. Multiple windows enhance the cabin's light-filled exterior.

Cottage in Wiscasset

Waterscape Cottage - private waterfront

This is where you want to stay! Away from all the traffic and noise of HWY 1, down a long driveway but super close to the village. Perched on the hillside with elevated panoramic views of the river and Wiscasset Harbor. This adorable little building is post and beam construction - comfy, quiet, peaceful on 34 acres of woodlands and river front. Want to squeeze in more kids? Talk to us. 2 quiet nonaggressive furry friends welcome. $20 per nt. per pet paid on arrival. Max pet fee $100.

Indoor spacesFamilyParking

The cottage features a single-story facade with grey siding and a well-maintained garden area. A gravel path leads to the entrance, flanked by outdoor seating that includes a round table and chairs. American flags are displayed, and the Sheepscot River is visible in the background.

4.96 out of 5 average rating, 99 reviews

Waterfront Getaway & Scenic View

A private waterfront cottage nestled away in the town of Edgecomb; “in the southern part of Lincoln County, which is situated upon the peninsula formed by the Sheepscot and Damariscotta Rivers, having Newcastle on the north and Boothbay upon the south. The cottage sits on an acre of land and is surrounded by beautiful forest and a view of the hallmark village, Wiscasset. Perfect place for couples, family, or friends to spend the summer/fall/vacation or getaway by the river's edge.

Indoor spacesFamilyLayout

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.

4.97 out of 5 average rating, 381 reviews

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.

KitchenFamilySolo travel

4.92 out of 5 average rating, 241 reviews

A two-story home is set on a spacious, grassy lot surrounded by trees. A paved driveway leads to the front, where a walkway is bordered by shrubs and greenery. A serene, wooded backdrop completes the peaceful atmosphere of the property.

Guest suite in Woolwich

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

Indoor spacesFamilySkiing

4.99 out of 5 average rating, 136 reviews

The modern retreat is nestled among trees, featuring a deck with outdoor seating and a picnic table. The structure showcases large windows, allowing natural light to fill the interior, with a welcoming red door standing out against the dark exterior.

Guesthouse in Newcastle

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!

KitchenIndoor spacesBackyard

The cottage features a traditional design with natural wood siding and a spacious screened-in porch, offering views of the surrounding landscape. Tall trees frame the home, and uneven rocky terrain leads to the base of the structure, enhancing the natural setting.

4.98 out of 5 average rating, 115 reviews

Coastal Cotton Cottage on Sheepscot Harbour

Coastal Cotton Cottage is on beautiful Davis Island in a peaceful setting by the sea. Open the French doors from the living room and step out onto the spacious front porch to watch the sun set across Wiscasset Harbor. This cottage features two bedrooms downstairs and one single bed in the loft. NEW UPDATES THIS SPRING! Our cottage has been recently updated with fresh paint, new towels and new coastal interior decor.

FamilyKitchenAccuracy

4.98 out of 5 average rating, 284 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 spacesHeating

5.0 out of 5 average rating, 157 reviews

Apartment in Wiscasset

Historic Elegance at The Sunken Garden Stay

Located in "The Prettiest Village in Maine," The Sunken Garden Stay is a charming apartment with views of the historic Sunken Garden landmark. This 1784 Colonial home is thoughtfully designed, blending open-plan living with warm, inviting spaces that reflect the character of its era. Complete with modern amenities, it offers the perfect mix of historic charm and contemporary comfort.

Indoor spacesFamilyCheckout

4.99 out of 5 average rating, 182 reviews

Home in Wiscasset

Victorian Charm in Wiscasset, Maine: Acorn Cottage

A TRULY NOSTALGIC MAINE VACATION STAY. This spacious 1903 Masonic Victorian home in the “Prettiest Village” in Midcoast Maine offers 3 bedrooms, 1.5 baths, and is steps from local landmarks like world famous “Red’s Eats” for a lobster roll, boutique shops, antiques, art galleries, and restaurants. Just up the road is the award-nominated “Alna Store”!

KitchenFamilyParks

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.

4.95 out of 5 average rating, 117 reviews

Sheepscot Harbour Village - 3 Bd Condo Waterview

Relax with the whole family at this peaceful place to stay. This newly renovated and well kept cottage features water views and easy access to all attractions. Located with in Sheepscott Bay Village with Deep Water dock and on site restaurant (seasonal pop-up). You will be in the middle of it all.

FamilyIndoor spacesBathroom

4.88 out of 5 average rating, 1012 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

NO HIDDEN FEES THE PRICE IS THE PRICE + CLEANING! Charming, updated, 1920's cottage directly on the banks of the Sheepscot bay. Cottage has - one bedroom with queen bed, bistro table for two, sitting area with sofa and cable television, small convenience kitchen area (no stove), full bath, linens

KitchenIndoor spacesBarbecue

Popular amenities for Wiscasset family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 169 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 spacesValue

4.98 out of 5 average rating, 467 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

FamilyKitchenView

5.0 out of 5 average rating, 209 reviews

Cabin in Chesterville

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

KitchenIndoor spacesLayout

4.99 out of 5 average rating, 389 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

Indoor spacesKitchenHiking

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!

KitchenIndoor spacesCheckout

4.98 out of 5 average rating, 307 reviews

4.9 out of 5 average rating, 145 reviews

Bus in Durham

Solar Powered Bus in Forest | Hot Tub + Wellness

Indoor spacesKitchenCheck-in

4.98 out of 5 average rating, 173 reviews

Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

Indoor spacesKitchenOutdoor spaces

4.97 out of 5 average rating, 116 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

KitchenIndoor spacesParking

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 500 reviews

A charming log cabin nestled among lush greenery, featuring a sloped roof and multiple windows. A picnic table is positioned in front, surrounded by natural landscaping. The peaceful outdoor setting invites relaxation and exploration in the surrounding forest.

Cabin in Boothbay

Simple Boothbay Log Cabin on Water

Indoor spacesKitchenQuiet

4.96 out of 5 average rating, 105 reviews

The two-story cottage features a welcoming front porch with a green roof and an American flag. A gravel driveway leads to the house, surrounded by trees and green lawns, offering a peaceful and private setting.

Home in Bristol

Coastal Maine Retreat · Fire Pit · Walk to Harbor

FamilyKitchenHeating

5.0 out of 5 average rating, 180 reviews

A spacious waterfront view captures the serene Kennebec River, adorned with small islands and surrounded by lush green trees. The sky is bright blue with scattered clouds, reflecting a tranquil natural setting.

Guesthouse in Bath

Waterfront Sunrise Cove Cottage

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 156 reviews

A rustic sliding barn door opens to reveal a laundry area just off the main living space. The walls are painted in a soothing green color, and warm sunlight filters through a window, highlighting the wood flooring and decorative accents above the door.

Apartment in Newcastle

Historic charm, Modern amenities, Walk downtown

KitchenFamilyHiking

4.78 out of 5 average rating, 132 reviews

Townhouse in Boothbay

Captain Fuller House: Boat Builders Retreat - Main

Indoor spacesKitchenAccuracy

4.91 out of 5 average rating, 449 reviews

Home in Bath

Beautiful Fall River Retreat

Indoor spacesKitchenPets

4.9 out of 5 average rating, 205 reviews

An inviting interior of the yurt features a queen-sized bed adorned with bright linens. A wooden lattice wall complements the natural wood flooring. A small table with chairs is situated nearby, and an acoustic guitar rests against the wall, adding a touch of warmth to the space.

Yurt in Dresden

Wild Acres Yurt on 36 acres.

KitchenIndoor spacesShared spaces

4.98 out of 5 average rating, 154 reviews

Home in Georgetown

Cottage on Todd Bay

KitchenIndoor spacesParks

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 245 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.

Apartment in Brunswick

Charming Saltwater Farm apartment

Indoor spacesKitchenValue

4.94 out of 5 average rating, 113 reviews

Home in South Thomaston

Large private area, close to Rockland

FamilyKitchenCondition

4.97 out of 5 average rating, 174 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!

KitchenFamilyValue

Home in Old Orchard Beach

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

KitchenFamilyOutdoor spaces

4.95 out of 5 average rating, 155 reviews

4.93 out of 5 average rating, 194 reviews

Cabin in Freeport

Cozy romantic A-frame by a woodland stream - 25

Indoor spacesFamilyCheck-in

4.95 out of 5 average rating, 700 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

FamilyKitchenAmenities

5.0 out of 5 average rating, 113 reviews

A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.

Apartment in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

FamilyKitchenGetting around