Family-friendly holiday rentals in Gray

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Top-rated family-friendly rentals in Gray

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

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Top guest favourite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham
4.95 out of 5 average rating, 179 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Top guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 441 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Top guest favourite
A serene duplex apartment is surrounded by lush greenery, with sunlight filtering through the trees. The exterior features light blue siding, multiple windows, and a neatly maintained lawn. A gravel path leads to a natural area, enhancing the peaceful setting.
Flat in Gray
4.96 out of 5 average rating, 169 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Top guest favourite
A tiny house with a grey exterior sits nestled among lush greenery and colorful flower beds. It features tall windows that allow natural light to flow in, and a bright red door that adds a pop of color. Surrounding steps made of stones lead up to the entrance.
Tiny home in Durham
4.99 out of 5 average rating, 371 reviews

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Top guest favourite
The kitchen features white cabinetry and a modern stainless steel stove. A round wooden table, set with blue placemats, includes a vibrant floral centerpiece. Natural light streams through the window, illuminating the space, which is equipped with essential appliances and ample counter space.
Guest house in Freeport
5 out of 5 average rating, 216 reviews

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse

Welcome to our spacious 1000 sq. ft. Maine barn guesthouse! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Top guest favourite
The exterior of a red barn-style home is surrounded by lush greenery and colorful flower beds. A patio setup includes comfortable seating, a dining table with an umbrella, and a fire pit on a pebbled area, providing an inviting outdoor space.
Home in New Gloucester
4.97 out of 5 average rating, 145 reviews

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Guest favourite
A cozy living area features a warm color palette with a sectional sofa adorned with textured blankets and cushions. A rustic coffee table sits in front of a mounted television. Natural light floods the space, highlighted by wall art depicting wildlife and an appealing area rug.
Cottage in Yarmouth
4.95 out of 5 average rating, 151 reviews

Modern cozy cottage in historic coastal Maine

Contemporary, newly-renovated cottage between Portland and Freeport. Spotless interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and washer/dryer. EV charging available. Walk down Main Street to shops, restaurants, and the scenic Royal River. Easy drives to downhill skiing and iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Half way between Boston and Sugarloaf. Your ideal base for Maine adventures.

Top guest favourite
A compact sleeping area features a queen-sized bed with a decorative white throw. Flanking the bed are two bedside tables, each topped with a lamp. Neutral-colored walls and soft lighting create a calm and inviting ambiance.
Flat in Windham
4.98 out of 5 average rating, 176 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Top guest favourite
A charming red cottage is nestled among tall trees, with a sloped roof showing patches of moss. The front features a large window and a welcoming yellow door, while a grill is visible on the side patio. The peaceful lakeside is glimpsed through the trees.
Cottage in Gray
4.91 out of 5 average rating, 220 reviews

Sunset Haven - Little Sebago Lake

Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.

Guest favourite
The image features a studio layout with four sections. A cozy sitting area includes a blue sofa and armchair, facing a smart TV. A table set for dining is seen next to a modern kitchen. A spacious king bed is presented with decorative pillows, and a coffee table adorned with tasteful decor completes the scene.
Flat in Westbrook
4.92 out of 5 average rating, 118 reviews

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

Top guest favourite
A cozy bedroom features rustic wooden paneling and a sloped ceiling. A spacious bed with red and white bedding sits next to a wooden nightstand with a lamp. Additional storage baskets are arranged nearby, and light filters in through a window decorated with a sheer curtain.
Home in Cumberland
4.95 out of 5 average rating, 322 reviews

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a group of 6 or a couple of 2 to unwind.

Top guest favourite
A cozy living area is showcased, featuring a light grey sofa and a patterned armchair. A glass coffee table rests in the center, surrounded by natural light. Kitchen space is visible in the background, complemented by wooden accents and white cabinetry.
Guest house in Windham
4.99 out of 5 average rating, 277 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Popular amenities for Gray family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Gray

  • Total holiday rentals

    Explore 80 holiday rentals in Gray

  • Nightly prices starting at

    Gray holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 3,500 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 of Gray holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Gray rentals

  • 4.9 Average rating

    Gray stays are highly rated by guests – averaging 4.9 out of 5!