Family-friendly vacation rentals in Winslow

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winslow

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

0 of 0 items showing

1 of 3 pages

Superhost

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)

Superhost

The modern kitchen and living area feature light wood ceilings and ample natural light from large windows. A comfortable sectional sofa and a wooden dining table are complemented by sleek cabinetry and appliances, creating a warm and inviting gathering space.

Cabin in Jackson

4.99 out of 5 average rating, 146 reviews

Wall of Windows - Super Clean & Solar-powered

This newly constructed 850 sq ft cabin features a wall of windows and is located on a 30 acre forest. It is perfect for those seeking a peaceful and cozy space to relax and breathe deeper while experiencing the brilliance of Mid-Coast Maine. Wake up to the gentle morning sun cresting over the trees, linger at night under the magic and mystery of a star-filled sky, and witness what all four seasons have to offer. Belfast and Unity are close w/ Bangor, Camden, Rockland, & Acadia - easy day trips.

Superhost

A cozy interior of the RV is displayed, featuring a black sleeper sofa adorned with two light-colored pillows. A wooden dining table is positioned nearby, complemented by a blue-green chair. A small kitchenette and bathroom area are visible in the background, with natural light filtering through the window.

Camper/RV in Palermo

4.92 out of 5 average rating, 104 reviews

Camp at Shale Creek Homestead

Stay with us at Shale Creek homestead! No cleaning fee!! Come enjoy the charm of rural Maine! Countless beautiful ponds and lakes minutes away. Spectacular views of the Milky Way on clear nights and much more! Short drives to the Belfast/costal areas and Augusta. A manageable distance from the mountains of western Maine. Beautiful Branch pond at the end of the street. Lake St. George and China Lake under 10 minutes away. A Great location to enjoy Maine Kayak rentals available on site

Superhost

A two-story house showcases a charming design with a gray exterior and red front doors. Green trees frame the property, providing a natural backdrop. The inviting driveway leads to the entrance, with windows allowing for ample natural light.

Home in Oakland

4.95 out of 5 average rating, 133 reviews

The Modern Maine Retreat

Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

Superhost

A deck area features two green Adirondack chairs positioned to face the tranquil waters of East Pond. Natural greenery from surrounding trees provides a sense of privacy, enhancing a peaceful atmosphere for relaxation by the lake.

Cottage in Oakland

5 out of 5 average rating, 120 reviews

The Rocky Road Camp on East Pond

Welcome to camp life on East Pond. A 1 bedroom home located in Oakland Maine. Your quiet weekend getaway awaits you. Located in central Maine. You will be about a 60 mile drive to the coast or about a 70 foot walk to the lake. Oakland is just a 20 minute drive to Waterville where both Colby and Thomas Colleges are located. East Pond is the host of several area summer camps. The camp will give you beautiful views of the lake. Sit on the deck and enjoy the loons and other lake activity.

Superhost

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, 122 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.

Superhost

A spacious living room features a large sectional sofa adorned with colorful cushions. A decorative area rug rests on hardwood flooring, complementing the light walls and artwork. A lamp emits soft light beside the sofa, while a potted plant adds a touch of greenery.

Home in Waterville

4.85 out of 5 average rating, 203 reviews

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Superhost

An outdoor soaking tub with a white finish is positioned near the water's edge, surrounded by a gravel area. String lights hang overhead, providing soft illumination. A serene view of the lake is visible, framed by lush trees, as evening twilight casts a calming atmosphere.

Cottage in Sidney

4.91 out of 5 average rating, 143 reviews

Waterfront Cottage

The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

Superhost

A serene outdoor area is framed by lush greenery and trees, showcasing vibrant orange flowers in the foreground. A meandering stone path leads towards a gathering area in the distance, partially visible through the foliage.

Home in Sidney

4.86 out of 5 average rating, 100 reviews

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Superhost

An open living area features a dark futon sofa and a plush grey armchair. A kitchen with light wood cabinets and modern appliances is visible in the background. A framed landscape artwork adorns the wall above the kitchen counter, and light wood flooring runs throughout the space.

Guesthouse in Unity

4.97 out of 5 average rating, 237 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

Superhost

A dining area is presented with a large wooden table, surrounded by metal chairs. Natural light enters through a nearby window, illuminating the space. A decorative bowl filled with flowers sits at the center of the table, enhancing the inviting atmosphere. Simple wall art complements the decor.

Apartment in Waterville

5 out of 5 average rating, 120 reviews

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

This spacious home of approximately 1,200 square feet is just 1.1 miles from I-95 and located on the ground floor of a charming, two family home completely renovated and tastefully furnished in 2020. Here the “modern design” and “charming rustic feel” mix perfectly. BONUS: Guests have access to the backyard! The private yard boasts a patio set, fire pit, garden, fence and trees along the property line.

Superhost

The kitchen features light-colored cabinetry and a large island with seating for four. A spiral staircase is visible, leading to the upper levels. Natural light is provided by windows above the sink and in the dining area, which includes a wooden table and chairs.

Apartment in Pittsfield

4.89 out of 5 average rating, 102 reviews

Loft Retreat

Welcome to our enchanting loft retreat! Our thoughtfully designed apartment offers a serene escape with a touch of sophistication. Ascend the spiral staircase to discover a cozy bedroom complete with a work space and reading nook. Hidden up a trap door on the third level are two twin beds for the nimble. A full deck complete with a small fire pit is available in the warmer months. Your getaway awaits!