Kid-friendly vacation rentals in Winthrop

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Top-rated kid-friendly rentals in Winthrop

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

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Top guest favorite

The exterior of a modern A-Frame cabin is depicted, featuring a dark blue metal roof and large windows that reflect the surrounding greenery. The structure is framed by trees, showcasing a harmonious blend of architecture and nature.

Cabin in Chesterville

5 out of 5 average rating, 139 reviews

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)

Top guest favorite

A spacious private room features a large bed adorned with soft bedding, flanked by modern lamps. Natural light streams in through the door, which opens to a serene outdoor view. A decorative pillow with a sunflower adds a touch of color to the space.

Guest suite in Monmouth

4.98 out of 5 average rating, 170 reviews

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.

Guest favorite

The exterior of a charming 1900s home is visible, showcasing a light-colored facade with a prominent red door. Sunlight filters through the branches of nearby trees, creating a welcoming ambiance in the front yard.

Home in Winthrop

4.73 out of 5 average rating, 41 reviews

Central downtown & beach area, fish from backyard

Enjoy the beautiful Lakes Region of central Maine! This charming 1900's home is on a quiet street, walking distance to Lake Maranacook town beach, and a minute stroll to Downtown Winthrop. Bring your kayaks and kayak from the backyard to Annabessacook lake! With 4 lakes, hiking trails on Mount Pisgah, boating, winter skiing nearby & ice fishing. Winthrop has all the outdoor fun! 2 bdrms & 1 bath on the 1st level & the entire 2nd level the ideal kids bedroom/hangout. All new furniture & bedding.

Guest favorite

A large, rugged stone fireplace serves as a focal point in the living area, featuring a sturdy mantel decorated with candles and greenery. A wooden staircase curves next to the fireplace, leading to the upper level. A decorative plant is placed in front of the fireplace.

Home in Monmouth

4.9 out of 5 average rating, 67 reviews

Spacious Lakeside Comfort - Fall/Winter Wonderland

This spacious home is just steps from the shore of Anabessacook Lake. Here you will enjoy the comfort and luxury of a well-equipped house, surrounded by the best of what Maine has to offer. The Red Top House features an incredible stone fireplace, large screened porch, and stone patio with outdoor fire pit. Bedrooms are comfortable with water views. The kitchen is very well equipped for the whole family. Rental includes use of non-motorized boats and firewood. Ice fishing is steps away!

Top guest favorite

A spacious dome tent is nestled among tall trees, with sunlight filtering through the leaves, creating a warm glow. The forest floor is covered with soft earth and scattered leaves, enhancing the natural surroundings, while the calm ambiance invites visitors to relax and enjoy the scenery.

Island in Monmouth

4.99 out of 5 average rating, 236 reviews

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, 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.

Top guest favorite

A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.

Home in Hallowell

4.98 out of 5 average rating, 141 reviews

Hilltop Retreat with A/C, Hot Tub & Sauna

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.

Guest favorite

The kitchen features wooden cabinets and a granite countertop. A round dining table with four chairs is situated centrally. Stainless steel appliances, including a refrigerator and a stove, are visible, along with various kitchen utensils and supplies arranged on the countertop.

Apartment in Augusta

4.81 out of 5 average rating, 120 reviews

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.

Top guest favorite

A serene landscape captures a vibrant sunset reflected on calm water. The sky displays shades of orange and pink, blending into deep purple hues, while the silhouette of trees lines the horizon. The tranquil scene conveys a peaceful natural setting.

Loft in West Gardiner

4.97 out of 5 average rating, 191 reviews

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.

Superhost

A warm cabin interior features wooden walls and a high ceiling. A comfortable sofa is complemented by decorative pillows. A wooden ladder leads to a loft area. A TV is positioned on a rustic console, and a dining table sits near a window, providing natural light.

Cabin in Monmouth

4.86 out of 5 average rating, 37 reviews

The Woodland Lodge

Looking for a cozy family-friendly get away in the beautiful woods with access to a shared beach on Annabessacook Lake, look no further than The Woodland Lodge. Located in Monmouth ME, the cabin is close to the public boat launch for Cobbosseecontee Lake and Whittier Woods trails. It is 30 minutes to Augusta Regional airport, 1 hour to Portland Jetport, and 90 minutes to Sugarloaf. Enjoy the peaceful woods, shared beach access, and beautiful hiking trails nearby!

Superhost

A charming cottage is nestled among trees along the lakefront, featuring a sloped roof and large windows. A wooden dock extends into the water, with steps leading up to the home, providing easy access to the serene surroundings.

Home in Winthrop

5 out of 5 average rating, 4 reviews

Serene Lakeside Retreat

Relax with the family at this peaceful lakefront retreat on Cobbosseecontee Lake. Lovingly remodeled with care, this cozy 2-bedroom cottage blends Maine cabin charm with modern updates. Enjoy a full kitchen, spacious living area, two baths, a screened porch, and a deck with stunning lake views. Kayaks included! Unwind, explore, and make lifelong memories at this beautiful waterfront escape.

Guest favorite

A serene lakeside view showcases a grassy area with turquoise Adirondack chairs arranged around a stone fire pit. Two kayaks and a paddleboard rest nearby, while a dock extends into the water where a boat is anchored. Tall trees frame the scene, enhancing the natural beauty.

Cottage in Winthrop

5 out of 5 average rating, 15 reviews

Little Landing Cottage Lakefront Dock Kayaks

Cozy lakefront retreat with dock, kayaks, and sunsets. Walk to marina & restaurant. Pet-friendly and peaceful year-round. Slow down, breathe deep, and let the lake carry your worries away. This charming cottage invites you to reconnect—with nature, loved ones, and yourself. Perfect for couples, small families, or close friends seeking a cozy and quiet escape just steps from the water.

Top guest favorite

A cozy bedroom features a queen bed with a decorative quilt and a floral throw pillow. The room is illuminated by warm bedside lamps. Exposed wooden walls and sloped ceilings add character, while a mirror and nightstand offer functional elements.

Guest suite in Hallowell

4.95 out of 5 average rating, 189 reviews

Apartment G - Best view in Hallowell

The unit is located in a 7-room house NOT occupied by the owners just two blocks from downtown. The entrance is not yet private. Entry is through a common door next to the parking spot. There is a well-stocked, full kitchen/TV room four power recliners and balcony overlooking the Kennebec River. The bedroom has a queen bed with second TV and spacious, tiled bathroom.