Family-friendly holiday rentals in Woolwich

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Woolwich

  • Total holiday rentals

    Explore 40 holiday rentals in Woolwich

  • Nightly prices starting at

    Woolwich holiday rentals start at $153 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,070 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Woolwich holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woolwich rentals

  • 4.9 Average rating

    Woolwich stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated family-friendly rentals in Woolwich

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

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Guest favourite
The serene view showcases a sunrise over the calm waters of the Sasanoa River, reflecting golden hues. Lush greenery frames the scene, while the distant treeline adds depth to the landscape. Soft clouds linger above, enhancing the tranquil atmosphere of the setting.
Cottage in Woolwich

Pet Friendly Audubon Bring Your Fishing Gear!

Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

KitchenFamilyAccuracy

4.91 out of 5 average rating, 227 reviews
Top guest favourite
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.
Guest house 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!

KitchenFamilyHospitality

4.88 out of 5 average rating, 104 reviews
Top guest favourite
A waterfront view is captured from a deck, showcasing calm waters surrounded by a lush landscape of colorful trees. The bright blue sky reflects on the surface of the creek, while greenery provides a serene foreground.
Home in Bath

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

FamilyKitchenSleep quality

4.99 out of 5 average rating, 132 reviews
Top guest favourite
A screened-in porch features comfortable seating arranged around a central table. Natural wood beams adorn the ceiling, and a ceiling fan is present for air circulation. Views of the outdoor area can be appreciated through the screens, enhancing relaxation in this inviting space.
Home in Bath

Little Cottage on the Kennebec

77 Washington is tucked along the shores of the Kennebec River in Bath. Centrally located along the coast between Boothbay Harbor and Freeport, both of which are about 30 min drive. We are adjacent to the South End Boat Launch, your portal to the open ocean! The cottage is just a short walk to the Maine Maritime Museum and only 15 miles from both Popham Beach State Park and Reid State Park. Master bedroom has private balcony and first floor offers cute galley kitchen and screened porch.

FamilyIndoor spacesBack garden

4.94 out of 5 average rating, 132 reviews
Guest favourite
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.

Indoor spacesKitchenParking

4.97 out of 5 average rating, 387 reviews
Superhost
The sleeping area features a spacious bed covered with light bedding, contrasted by a colorful area rug. A cozy yellow armchair is positioned nearby, while the sloped ceiling adds character to the room. A simple lamp offers additional lighting.
Loft in Bath

Apartment over shops in Bath Historic District

Light and bright upstairs loft style apartment with huge windows and style to spare. This is one of three apartments in the upper floors of an awesome renovated historic building in the center of Downtown Bath's historic district. Large livingroom windows look out over Centre Street where you'll find restaurants, a bookshop, bakery, art gallery and Bath Natural Market. A shared washer/dryer is in the building and there is off street parking for your use, free (one car).

Indoor spacesKitchenQuiet

4.73 out of 5 average rating, 153 reviews
Guest favourite
The living area features a soft teal sofa positioned across from a wooden coffee table. A rug covers the floor, and natural light enters through large windows adorned with white curtains. A small lamp and a potted plant add to the welcoming ambiance.
Home in Bath

The Cottage

Welcome to The Cottage—your cozy getaway in the heart of Bath, Maine! Perfectly situated near charming coastal towns, beautiful beaches, and scenic hiking trails, this retreat offers a comfy living area, fully equipped kitchen, and four inviting bedrooms. Sip your morning coffee from the sunny dining room window seat, or wind down by the fire pit out front. Note: The Cottage is attached to the owner’s home, but you’ll have full privacy throughout your stay.

Indoor spacesKitchenAmenities

4.95 out of 5 average rating, 133 reviews
Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.

Indoor spacesKitchenLayout

5.0 out of 5 average rating, 155 reviews
Top guest favourite
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 spacesFamilySleep quality

4.92 out of 5 average rating, 243 reviews
Guest favourite
A serene view of the Kennebec River is framed by lush green trees. The landscape features a wooden bench in the foreground, overlooking the water, while distant homes and docks are visible across the river. The sky displays a mix of soft colors as clouds gather.
Home in Bath

Spectacular River Retreat with Hiking Trails

Spectacular listing brought to you by seasoned Bath Superhosts! Enjoy sweeping views of the Kennebec River while cozying up by the fireplace. This modern art filled minimalist house sits on a bluff overlooking the Kennebec River and leads into Bath's peaceful Thorne Head Preserve, a vast network of trails that climb and hug the river's edge. It's just minutes away from downtown Bath, the historic and charming City of Ships.

Indoor spacesKitchenLocation

4.92 out of 5 average rating, 147 reviews
Top guest favourite
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).

FamilyKitchenQuiet

4.98 out of 5 average rating, 287 reviews
Top guest favourite
An entryway is displayed, featuring a nautical map mounted on the wall. A wooden bench sits beneath the map, accompanied by a woven bag hanging from hooks. A striped area rug lines the floor, complemented by a pair of sandals positioned nearby.
Guest suite in Bath

Bath Historic District Apartment

Located in the Bath historic district, this one bedroom apartment is located just a few blocks from downtown. The apartment has a queen bed in the bedroom and also a queen sleeper sofa in the living room. The home was built in the late 1700's, but with the recent upgrades, it now feels fresh with classic elements. Located in Midcoast Maine, this apartment is an quick drive to the beach, hiking trails and museums.

FamilyKitchenLocation

4.99 out of 5 average rating, 254 reviews

Popular amenities for Woolwich family-friendly rentals

Family-friendly home rentals with a hot tub

Family-friendly home rentals with a pool

Top guest favourite
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 spacesHeating

4.99 out of 5 average rating, 249 reviews
Top guest favourite
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 spacesGetting around

4.96 out of 5 average rating, 178 reviews
Top guest favourite
Home in Old Orchard Beach

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

FamilyKitchenLayout

4.96 out of 5 average rating, 158 reviews
Guest favourite
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

Indoor spacesKitchenGrill

4.95 out of 5 average rating, 702 reviews
Top guest favourite
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.
Flat in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

Indoor spacesFamilyDecor

5.0 out of 5 average rating, 116 reviews
Guest favourite
Home in South Thomaston

Large private area, close to Rockland

FamilyIndoor spacesBack garden

4.94 out of 5 average rating, 116 reviews
Top guest favourite
Flat in Portland

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Indoor spacesFamilyHiking

4.98 out of 5 average rating, 522 reviews
Top guest favourite
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

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 147 reviews

When is the best time to visit Woolwich?

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Avg. price$231 SGD$240 SGD$233 SGD$227 SGD$299 SGD$402 SGD$396 SGD$407 SGD$350 SGD$290 SGD$299 SGD$207 SGD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

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