
Family-friendly vacation rentals in Winthrop
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winthrop
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Welcome to The Nest - 1 bed, deck w/bath & parking
Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

Hammock Haven Island Dome
The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, and explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

The Escape on Elm
Our charming Airbnb is located in the heart of Gardiner Maine. Built in 1850, our historic home combines old-world charm with modern comforts. Enjoy the creaking hardwood floors, exposed beams, and coastal accents that create a calming, seaside vibe. The open layout offers a spacious living room with a sofa bed, Smart TV, books and board games. We offer a comfortable sleeping area with a queen bed. A full bathroom. Enjoy cooking in the fully equipped kitchen that opens to a private porch.

Hallowell Hilltop Home and Hot Tub
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Downtown Augusta - 2 Bedroom - Newly renovated!
Located at the heart of downtown Augusta, this 2 bedroom apartment is a wonderful choice when visiting Augusta Maine with another couple or if you just want more room then your average hotel! This 2nd floor apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is free parking and laundry available on site. Enjoy a stylish experience at this centrally-located place.

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.

Cozy, Efficiency Apartment with Hot Tub
Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Room B with private entrance, bathroom & hot tub
Room B has a full size bed with luxury mattress and private bathroom with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

The Barn by Swan Island: Whimsical, Comfy, & Fun!
Welcome to the place we call "The Barn by Swan Island." Located in Richmond, ME, just a short distance from the free boat launch to Swan Island in the Kennebec River. Originally built in the mid 1800's as an attached barn to our lovely Victorian home, we have completely renovated and remade the space into a fun, comfy, and whimsical AirBnB experience. An ideal location for a trip to Midcoast Maine!

Cozy Studio Flat, Belgrade Lakes Region
Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Rustic Ridge
More than a room!!! Private entrance, private bathroom, lots of space! Kitchen with stove/oven, freezer space, Lg. Mini Fridge. Water front and kayaks for use at your own risk. Remember, we are in rural Maine. You may find it helpful to print directions before you travel. Please call me if you need assistance.
Popular amenities for Winthrop family-friendly rentals
Family-friendly home rentals with a hot tub

Raven's Crossing - Kate's Cottage

Tiny A-Frame Romantic Getaway

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

LUX Designer Private Waterfront

Downtown Hideaway-Loft HotTub Modern Clean Private

Sunset Chalet Lakefront Hot Tub Game Room

Cozy Log Cabin incredible views - ski & hike

Cozy Cabin w/ Hot Tub & Fire Pit-Bike,Hike, Swim!
Family- and pet-friendly home rentals

McKeen's Riverside Retreat

Secluded, cozy cabin nestled in the Maine woods

Gorgeous Studio on the Kennebec

Cabin retreat just steps from adventure

Trailside Cabin

Riverside

Near Golfcourse | Dog Friendly | Lake Great Pond

Cozy Carriage House in Downtown Damariscotta
Family-friendly home rentals with a pool

Large Home with Great View next to horse farm

Sunny West End Guest Suite w/Harbor Views and Pool

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Slope Side | Ground floor | Hot Tub, Pool, Sauna

Steep Falls Escape, river & falls just steps away

Cozy Family Retreat with Saco River Access

Loft Apartment on Tree-Lined Street in Falmouth

Maine Hacienda w/hot tub & seasonal pool
Quick stats about vacation rentals that are family-friendly in Winthrop
Total rentals
40 properties
Nightly prices starting at
R1,206 ZAR before taxes and fees
Total number of reviews
1.2K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Destinations to explore
- Long Island Vacation rentals
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Island of Montreal Vacation rentals
- Laurentides Vacation rentals
- Quebec City Area Vacation rentals
- Mont-Tremblant Vacation rentals
- Salem Vacation rentals
- Laval Vacation rentals
- Waterfront rentals Winthrop
- Rentals with a washer and dryer Winthrop
- Rentals with a patio Winthrop
- House rentals Winthrop
- Rentals with outdoor seating Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a kayak Winthrop
- Rentals with lake access Winthrop
- Rentals with a fire pit Winthrop
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Belgrade Lakes Golf Club
- Willard Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Cliff House Beach
- Sunday River Golf Club
- Fox Ridge Golf Club
- Hunnewell Beach
- Maine Maritime Museum
- Black Mountain of Maine
- Brunswick Golf Club
- Bradbury Mountain State Park
- Eaton Mountain Ski Resort
- Portland Museum of Art
- The Camden Snow Bowl
- Farnsworth Art Museum
- Lost Valley Ski Area