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Family-friendly vacation rentals in Winslow

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Winslow family-friendly rentals

Family-friendly home rentals with a hot tub

A scenic view of the property showcases a field of wild Maine blueberries, transitioning from green to warm fall hues. The farmhouse and other structures are set against a misty backdrop of autumn foliage-covered hills, conveying the natural beauty of the surroundings.
Farm stay in Searsport
4.91 out of 5 average rating, 112 reviews

Latham Blueberry Farm for up to 6 guests.

AshleyRating, 5 stars10 months ago
We couldn’t have asked for a better stay at Latham blueberry farm. Doug and Brenda were incredibly helpful and friendly- they introduced us to the house and farm as soon as we checked in and were always available if needed. The beds were comfy, the kitchenette stocked, and the grounds were gorgeous. Their beautiful 1826 farm house was an authentic experience of staying on a farm- our kids loved feeding the animals (especially Ernie the pig and Moses the horse); picking fresh blueberries; and swimming and paddleboating in the private pond. Our hosts had great recommendations for local outings, and we loved chatting with them and playing with their puppy Jackie. Our family made lifetime memories.
Top guest favorite
A modern farmhouse is situated on elevated land, surrounded by trees. Its white exterior is complemented by large windows that reflect in the calm water below. The scenic scene is framed by lush greenery, creating a serene atmosphere.
Home in Woolwich
5 out of 5 average rating, 43 reviews

Amazing view, eagles, hot tub, 1 mi walk from Bath

GregoryRating, 5 stars1 week ago
Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.
Top guest favorite
An open kitchen and dining area features wooden cabinetry and a round table with four chairs. A stainless steel refrigerator sits next to an oven and gas stove. A spiral staircase leads to an upper level, while acoustic guitars are displayed, adding a musical touch.
Home in Holden
4.96 out of 5 average rating, 245 reviews

Central Chalet

IoanaRating, 5 stars2 weeks ago
We loved our time at Dwayne and Patti’s place! It definitely felt like a home rather than a hotel, which is exactly what we want when we book an Airbnb over a hotel. The musical instruments and hot tub were a hit with our group :) The location is amazing, close to both Bar Harbor (Acadia) and Bangor. We got to go to a concert and hiking during our stay, and we loved returning to our home base. I can’t want to be back!!
Top guest favorite
Apartment in Falmouth
4.91 out of 5 average rating, 200 reviews

Falmouth 3br near Town landing

EllenRating, 5 stars6 days ago
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.
Guest favorite
A wood-fired cedar hot tub sits on a deck, surrounded by trees. Two folding chairs are placed beside the hot tub, offering a serene spot for relaxation. The structure's screened-in porch provides a view of the surrounding nature.
Treehouse in Georgetown
4.97 out of 5 average rating, 340 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

EmilyRating, 5 stars1 month ago
We had the most wonderful staying here! A peaceful and relaxing getaway is exactly what we needed, and exactly what we received. The hot tub was the perfect touch. We couldn’t recommend this place more! Can’t wait to go back!
Top guest favorite
A spacious log cabin is featured, set in a natural landscape surrounded by trees. A wide wraparound deck is accessible via a wooden ramp, leading to a welcoming front door. Lush greenery and decorative plant beds border the cabin, complementing its rustic charm.
Cabin in Chesterville
4.89 out of 5 average rating, 53 reviews

Lakefront Log Cabin escape-boats-fishing-hot tub

NicholaRating, 5 stars7 months ago
Just returned from the most fantastic 2 weeks exploring the US which included a weeks stay at Kiwi Lodge. Where to start? This was exactly as described and the perfect base for exploring Maine. The property was spotless and has all the amenities needed for a comfortable stay. 3 beautiful bedrooms, 2 great sized bathrooms, wonderful living area and kitchen and fantastic games room. Hot tub was brilliant. The location on the lake is just perfect, we had the lake to ourselves and took the canoe out. Nearest town of Farmington has all the shops and cafes you’d need. The communication from Kay was great from the day we booked, and recommendations we took her up on were all absolutely spot on. Thank you Kay and thank you Kiwi Lodge for a holiday to remember!
Guest favorite
A private deck area showcases a hot tub, emitting a soft blue light. Two chairs are positioned nearby, with a decorative cushion displayed on one. Lattice fencing and greenery provide privacy, creating an inviting setting for relaxation at night.
Apartment in Topsham
4.87 out of 5 average rating, 549 reviews

Cozy hot tub haven

AshleyRating, 5 stars1 week ago
Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️
Guest favorite
The exterior of a two-story house is surrounded by a green lawn and neatly trimmed bushes. The home features multiple windows and a balcony. A flag is displayed on a pole, while trees and landscaping create a natural backdrop.
Cottage in Verona Island
4.89 out of 5 average rating, 171 reviews

Nashport on the Penobscot

DeanRating, 5 stars6 days ago
great stay for a relaxing weekend trip. perfect house for chilling but still drivable to Acadia. well stocked on the essentials, linens, and stunning views! host very responsive as well.

Family- and pet-friendly home rentals

Guest favorite
A quaint cottage is set amidst autumn foliage, featuring a simple design and exterior with light-colored siding. Its porch area is visible, surrounded by a grassy lawn scattered with fallen leaves, creating a serene outdoor space that invites relaxation.
Cabin in Madison
4.85 out of 5 average rating, 130 reviews

Charming cottage at the Lake!

KatherineRating, 5 stars8 months ago
Charming little cottage on the lake! Had a lot of fun, easy to get to town and the lake was serene and peaceful. Great place to stay!
Guest favorite
A charming white cottage with a sloped roof is situated near the water's edge. Orange window boxes add a pop of color to the exterior, while a stone patio features several wooden chairs. Lush greenery surrounds the property, providing a natural backdrop.
Home in Bath
4.91 out of 5 average rating, 344 reviews

Gorgeous Studio on the Kennebec

JamesRating, 5 stars1 week ago
Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!
Guest favorite
A charming log cabin nestled among lush greenery, featuring a sloped roof and multiple windows. A picnic table is positioned in front, surrounded by natural landscaping. The peaceful outdoor setting invites relaxation and exploration in the surrounding forest.
Cabin in Boothbay
4.95 out of 5 average rating, 444 reviews

Simple Boothbay Log Cabin on Water

DuncanRating, 5 stars2 weeks ago
Words literally cannot explain the feeling you get when you step onto this property. Picture perfect piece of heaven. I've never cried leaving a place before, that's the impact it had on me. I left a piece of my heart in that cabin. Already planning to go back. 🤙✌️💚
Top guest favorite
A spacious bedroom is furnished with a king-size bed featuring a plaid bedding set. Two windows allow natural light to enter, complemented by a bedside lamp. Wooden accents, including a wardrobe and a small table, enhance the room's warm ambiance.
Guest suite in Freeport
4.97 out of 5 average rating, 236 reviews

Waterfront Private Apartment only 5 min to LLBean!

VirginiaRating, 5 stars2 weeks ago
Wonderful stay, the place was in a beautiful location, walkable to Wolfe’s Neck Farm where we love to walk. My husband and I were there the first few days, then our adult daughter joined us for two nights. The place is small (described accurately) but the three of us found it very workable. The king bed was very comfortable. There was plenty of outside patio space to lounge and soak up the sun when it was out. This was a work trip for us as we were getting a property in a nearby town ready for sale. We didn’t have time to use the provided kayaks but hope to in a future stay. The hosts very friendly and accommodating, highly recommended this property.
Superhost
The interior features a vaulted wooden ceiling with exposed beams, showcasing a natural knotty pine finish. Decorative wildlife mounts, including a deer head and various metal art pieces, accentuate the rustic charm of the space.
Cabin in Carthage
4.94 out of 5 average rating, 193 reviews

Private Maine Camp

MaggieRating, 5 stars2 months ago
Great cabin for my family of 4 and our dog for a quick ski trip. I have 2 boys aged 14 and 11 who loved the loft area. We stayed to ski at Saddleback for 2 days, so was in the cabin l for just breakfast and then evening. Is described accurately in listing. Enjoyed our time!
Guest favorite
A charming cabin is set amidst greenery, featuring a sloped roof and wood siding. The front porch is equipped with two blue chairs, inviting relaxation. A gravel pathway leads to the entrance, surrounded by grass and small plants.
Cottage in Penobscot
4.82 out of 5 average rating, 104 reviews

Cozy cottage in the woods

MargaretRating, 5 stars9 months ago
Cute little cabin in the woods!! Super clean, check in was very easy. Nichole was very easy to communicate with. The cabin was perfect for a quick weekend. We would definitely stay again!
Guest favorite
A well-organized shelving unit displays an assortment of books, decorative items, and a vintage clock. A cozy area rug is visible in front of a comfortable gray sofa, while a sturdy coffee table sits in the center. Natural light filters in through nearby windows.
Guesthouse in Camden
4.92 out of 5 average rating, 247 reviews

Superb Location w/EV Hk up & Walk to town & ocean

AdrianaRating, 5 stars2 weeks ago
My husband and I stayed here with our dogs and loved it! The cottage was quaint and lovely …. And the location is perfect! Amanda was so kind and responsive! We will definitely be back when in Camden again 🌸🌲🌊
Guest favorite
A cozy living area features a black wood stove providing warmth. A wooden table is set with two glasses and a bottle, inviting relaxation. Windows offer views of the water, while comfortable seating is arranged nearby, enhancing the inviting space.
Guest suite in Penobscot
4.87 out of 5 average rating, 110 reviews

Waterfront Getaway on the coast of Maine.

MichaelRating, 5 stars2 months ago
As our last stay everything was very accommodating and comfortable. Great music, books, art and an expansive beautiful landscape. The stars at night are beyond amazing. Highly recommended.

Family-friendly home rentals with a pool

Top guest favorite
A spacious inground pool is enclosed by a chain-link fence, featuring a water slide and lounge chairs arranged around the perimeter. Lush green trees and a clear blue sky are visible in the background, creating a serene setting for relaxation and enjoyment.
Apartment in Cornville
4.87 out of 5 average rating, 134 reviews

Large Home with Great View next to horse farm

WilfredoRating, 5 stars2 weeks ago
Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!
Superhost
A historic lake-front cottage is presented with its red siding and white trim, featuring numerous windows that enhance natural light. A cupola tops the building, while a porch extends along the front. A sandy area in front leads to the water.
Cottage in Poland
4.61 out of 5 average rating, 18 reviews

Lake Beach House at Poland Spring Resort

Erin Rating, 5 stars10 months ago
Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!
Superhost
A serene tidal pool is depicted, reflecting soft pink and purple hues of the twilight sky. Rocky formations are gently scattered across the water's surface. The surrounding shoreline is outlined by a dense tree line, enhancing the natural beauty of the coastal landscape.
Home in Stonington

Kate's House at Spruce Harbor

ShokiRating, 5 stars9 months ago
Cannot imagine a better spot to relax with our family. A lucky spot for the owners and luckier for us that they share the rental with strangers.
Superhost
A serene view of Penobscot Bay at sunrise, featuring a pastel sky in shades of pink and purple. Small boats are visible on the water, while a lighthouse stands on the shoreline. A grassy area has benches and picnic tables, inviting outdoor enjoyment.
Apartment in Rockland

Heart of Rockland Maine

DeborahRating, 5 stars8 months ago
Aimee was wonderful to deal with. Her place was absolutely beautiful. we definitely picked the right place. the sunrises were so awesome. Rockland was a gorgeous little town.
Guest favorite
The kitchen features wooden cabinetry and a modern design with ample counter space. A stainless steel fridge and coffee maker are visible alongside a sleek electric stove. Four tan bar stools provide seating at the granite countertop, enhancing the functional layout.
Condo in Carrabassett Valley
4.93 out of 5 average rating, 46 reviews

Post & Beam, Ski-in/Ski-Out Birchwood Penthouse

AdrianRating, 5 stars8 months ago
Great spot, would rent again!
Superhost
An indoor pool area is highlighted by a spacious swimming pool with clear blue water. Natural light filters through skylights, illuminating the wooden beams overhead. Several white lounge chairs are arranged nearby, and a hot tub is visible in the background.
Home in Carrabassett Valley
4.84 out of 5 average rating, 69 reviews

SUGARLOAF, TRAILSIDE, 4-BDRM, & AC

EstherRating, 5 stars1 month ago
We had such an enjoyable stay we didnt want to leave! All agreed we would stay here again - such a beautiful quiet retreat. Steve was a responsive host with detailed instructions for checkin/checkout. It made everything perfect for my family.
Top guest favorite
A spacious living area features large windows that allow natural light to fill the room. Comfortable seating includes a striped sofa, a cozy armchair, and a coffee table set on a circular braided rug. A brick fireplace adds a rustic touch, creating a welcoming environment.
Condo in Carrabassett Valley
4.96 out of 5 average rating, 55 reviews

Cozy Ski In, Ski Out End Unit Condo

CynthiaRating, 5 stars2 months ago
Great place to stay for a family of 4. Very close to Snubber for skiing and hiking. Hope to stay again. Thank you!
Superhost
A log cabin is nestled among tall trees on a gentle slope. Large windows create airy views from the exterior, showcasing a front deck that extends along the house. The natural surroundings provide a peaceful and serene setting.
Home in Peru
4.95 out of 5 average rating, 218 reviews

the lake house

CarlaRating, 5 stars5 months ago
We had a lovely time at the cabin. Close to skiing yet peaceful and relaxing. We thoroughly enjoyed our stay ! Thank you!

Quick stats about vacation rentals that are family-friendly in Winslow

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$6,269 GYD before taxes and fees

  • Total number of reviews

    930 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore