Holiday houses in Gray

4.99 out of 5 average rating, 396 reviews

Cottage in Pownal

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

4.94 out of 5 average rating, 140 reviews

Home in Windham

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.

4.96 out of 5 average rating, 115 reviews

Guesthouse in Cumberland

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

4.95 out of 5 average rating, 143 reviews

Apartment in Gray

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.

4.93 out of 5 average rating, 154 reviews

Cabin in Raymond

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

4.99 out of 5 average rating, 136 reviews

Apartment in Windham

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.

Guest suite in North Yarmouth

4.98 out of 5 average rating, 112 reviews

open concept Guest Suite in southern Maine

A short distance to many nature trails, Bradbury Mountain, state parks and the rocky coastline. This North Yarmouth guest suite is nestled between all the breweries and restaurants Portland has to offer as well as the famous outlet shopping in Freeport. We are located in a unique location where you are able to go from the rocky coast to the hiking trails all within 30 minutes. The guest suite is perfect for quiet lodging after a day of exploring or visiting.

4.91 out of 5 average rating, 213 reviews

Cottage in Gray

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.

4.95 out of 5 average rating, 300 reviews

Home in Cumberland

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.

4.96 out of 5 average rating, 225 reviews

Guesthouse in Cumberland

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.

4.95 out of 5 average rating, 281 reviews

Farm stay in Gray

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

4.97 out of 5 average rating, 130 reviews

Guest suite in Gorham

Farmhouse stay, near lakes and St. Joe's College

Charming 2 story, 2 bedroom antique farmhouse apartment within walking distance to a quaint pond. Located minutes from St. Joseph's College, Sebago Lakes region, fly-fishing on the Presumpscot River, premier mountain biking and hiking trails. 15 miles to downtown Portland’s famed restaurants, breweries, and shopping.

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Other great holiday rentals in Gray

5 out of 5 average rating, 3 reviews

Tiny home in Casco

The Casco Tiny house!

MaliaRating, 5 stars3 months ago

Cody is the greatest host. He was very genuine, and responsive with everything. This little home will be one to remember. It was very comfortable and peaceful. I would come back again! 😊🙏🏽

5 out of 5 average rating, 51 reviews

Cabin in Freeport

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean

PaigeRating, 5 stars1 week ago

Instructions on how to find were clear and prevented us from driving in circles due to incorrect location on gps. Cabin was easy to check in and clean. Location was perfect for our trip plans and provided great scenery! 10/10 recommend.

4.88 out of 5 average rating, 50 reviews

Cabin in Gray

Waterfront Access w Kayaks, Private Deck, Firepit

LourdesRating, 5 stars1 week ago

Very relaxing place. Caught some good sized bass. My kids enjoyed the blocks and the games. Lots of opportunities to gather together around the house. We also enjoyed the bottom floor and had fun playing with the hook game. Amy was very welcoming and her recommendations and detailed notes made our trip a delightful. Major plus for it being pet friendly!

4.94 out of 5 average rating, 53 reviews

Cottage in Gray

Charming 3 bedroom cottage on Notched Pond

MatveiRating, 5 stars8 months ago

It was a wonderful 2 days we sent there! Great location, beautiful and clean house the area around the house is stunning We are grateful to the host that we had this opportunity!

4.88 out of 5 average rating, 26 reviews

Cabin in New Gloucester

Romantic Hidden Cottage!

AdriannaRating, 5 stars2 weeks ago

Misty’s cabin was very cute, cozy, and private. We loved soaking in the hot tub and listening to the frogs and crickets at night! The bed is kind of firm and springy but was doable for a short stay. Would definitely recommend grabbing breakfast at the cafe 1055 across the street, we ended up stopping there twice and it was delicious both times. Misty had great communication during our stay as well!

5 out of 5 average rating, 4 reviews

Tiny home in Casco

Maine tiny home at the Lake with direct lake view!

JoshRating, 5 stars1 week ago

What a great a place! The views of the lake were even better than I imagined. We also loved being so close to the Naples causeway.while still being able to get into Portland easily. We were greeted by the sound of loons daily and woke up to views of the lake - even from bed! Andy was above and beyond in responsiveness and he and his wife clearly want to make sure your trip is perfect. Thanks so much for everything Andy!

4.97 out of 5 average rating, 67 reviews

Tiny home in Pownal

Little FoxHill, a home in the woods by a brook

TrippRating, 5 stars2 weeks ago

A wonderful enchanting time in Maine. The hosts were amazing and made the short trip magical. Michael offered me his high end telescope going beyond superhost status. Little Fox and the property were a little slice of heaven on Earth.