
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.

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.

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.

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.

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.

Birch Ledge Guesthouse--Four Season Maine Getaway
Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

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.

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.

Cozy camp near highland lake
If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

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.

Suite at Maine Mystic Gardens
This cozy, country attached "mother-in-law" suite with garden views is an 800 square foot suite with two bedrooms (11 x 15’ and 8 x 10’), one full bathroom, a living room with flat screen cable TV and a fully stocked kitchen, ready to be utilized. There is a separate entrance to the facility and parking for multiple cars (one spot under the deck). Outside, there is a large deck with a table and grill for outdoor seating and grilling.

Cottage Under a Crabapple Tree
Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Beautiful Coastal Maine Getaway
Set back among backdrop of tall pines on Maine's coast is our immaculately clean, and very private 4 bedroom, 2 bath home in Yarmouth. Quiet and secluded, and perfectly located between Portland and Freeport, it's an amazing place to decompress with family and friends. Our home comes complete with absolutely everything you need to enjoy your stay!
Popular amenities for Gray family-friendly rentals
Family-friendly home rentals with a hot tub

Solar Suite surrounded by Nature

LUX Designer Private Waterfront

Romantic New England Historic Schoolhouse c1866

Cozy Rock Cabin #thewaylifeshouldbe

Loft Apartment on Tree-Lined Street in Falmouth

Apt in Victorian Mansion w/ Hot Tub & Parking

Luxury Year-round Hobbit House w/ private hot tub

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes
Family- and pet-friendly home rentals

Sunny 2-BR 5 min to Bates & River Trails

On the water Boathouse!

Scandinavian Lakehouse - King Bed - Pet friendly

Private Guesthouse in the Woods

Private Sauna+Near Beach+FirePit+Forest View+Pond

Yurt on Chebeague Island

Cozy Cottage on Highland Lake

Charming Cottage With Spectacular Water View
Family-friendly home rentals with a pool

Cozy Studio Flat, Belgrade Lakes Region

Resort-like 2 bed/1 bath - seasonal pool/hot tub

Family friendly + Mountain Views @amountainplace

Cozy Top Floor-1 King, Mtn View, Jetted Tub, Pools

KimBills’ on the Saco

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

An Amazing Mountain Getaway!

Maine Hacienda w/hot tub & seasonal pool
When is the best time to visit Gray?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £167 | £149 | £159 | £149 | £176 | £227 | £260 | £286 | £223 | £186 | £170 | £167 |
| Avg. temp | -6°C | -4°C | 1°C | 6°C | 12°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -2°C |
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!
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- Rentals with a patio Gray
- Waterfront rentals Gray
- Pet-friendly rentals Gray
- Rentals with a kayak Gray
- Rentals with a fireplace Gray
- Rentals with a firepit Gray
- House rentals Gray
- Rentals with beach access Gray
- Rentals with lake access Gray
- Cottage rentals Gray
- Rentals with outdoor seating Gray
- Rentals with a washing machine and dryer Gray
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Story Land
- Sunday River Resort
- Scarborough Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Diana's Baths
- King Pine Ski Area
- Dunegrass Golf Club
- Belgrade Lakes Golf Club
- Willard Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Gooch's Beach
- Parsons Beach
- Wolfe's Neck Woods State Park
- Cliff House Beach
- Crescent Beach State Park
- Ferry Beach




