
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.

Modern Brunswick Tiny Home near Bowdoin & Downtown
A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

Trailside Cabin
Come & play in the beautiful mountains of western Maine! Cozy, rustic cabin for two. Enjoy miles of multi use trails right off the front steps! If you decide to venture away from the cabin, Rangeley's Saddleback Mt & Sugarloaf USA are both 35 miles away & the college town of Farmington is just 15 minutes south. Our cell service is terrific, but there's no tv or wifi...come to the woods & unplug!

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

Treehouse With Hot Tub Close to Sunday River!

Raven's Crossing - Kate's Cottage

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

SkyView Treehouse | Lakefront • Private Hot Tub

Cozy Log Cabin incredible views - ski & hike

Lakefront: Private Hot Tub, Sauna & Free Massages!

Belfast City Park Ocean House

Cozy Rock Cabin #thewaylifeshouldbe
Family- and pet-friendly home rentals

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Gorgeous Studio on the Kennebec

Near Golfcourse | Dog Friendly | Lake Great Pond

Riverside

Cozy Carriage House in Downtown Damariscotta

Mountain View Studio

Sheepscot Harbour Cottage/waterview

Lakefront Log Cabin on Pleasant Lake
Family-friendly home rentals with a pool

Attitash Studio | 5min to Storyland| Pools

Sunny West End Guest Suite w/Harbor Views and Pool

KimBills’ on the Saco

3 Bears Glen, Across from Story Land, near skiing

Fireplaced Mountain King Suite w/Hot Tubs & Pools

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

Stunning 2BR with Mountain Views | Nordic Village

Steep Falls Escape, river & falls just steps away
Quick stats about vacation rentals that are family-friendly in Winthrop
Total vacation rentals
Explore 40 vacation rentals in Winthrop
Nightly prices starting at
Winthrop vacation rentals start at R1,220 ZAR per night before taxes and fees
Verified guest reviews
Over 1,170 verified reviews to help you choose
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 of Winthrop vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals
4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
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