Are there pet-friendly vacation rentals in Gray?

Four-legged friends are welcome in Gray. Choose from more than 30 vacation rentals for guests traveling with pets.

Are there vacation rentals with a dedicated workspace in Gray?

Yes! Work meets play with ease at over 40 vacation rentals in Gray featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do house rentals in Gray have a bbq area?

Absolutely! We offer over 30 house rentals with a bbq area in Gray. Enjoy a tailored experience with all the comforts you desire.

How much does it cost to stay in cottage rentals in Gray?

Experience the best of Gray with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Gray have wireless internet?

Absolutely! We offer over 60 house rentals with wireless internet in Gray. Enjoy a tailored experience with all the comforts you desire.

Do cottage rentals in Gray have air conditioning?

Absolutely! We offer over 10 cottage rentals with air conditioning in Gray. Enjoy a tailored experience with all the comforts you desire.

Are there family-friendly cottage rentals in Gray?

Gray has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

What are the most popular amenities for Cottage Rentals in Gray?

Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Gray vacation rentals

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Top-rated vacation rentals in Gray

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious wooden deck is presented, featuring two black Adirondack chairs positioned comfortably. A small potted tree adds a touch of greenery, while the surrounding snowy landscape reflects a serene outdoor atmosphere.

Cottage in Pownal

4.99 out of 5 average rating, 396 reviews

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.

Top guest favorite

A bright and airy kitchen area features modern cabinetry and sleek countertops. Stainless steel appliances, including an oven and microwave, are positioned for convenience. Natural light filters through a nearby window, illuminating the entryway with a simple coat rack beside the door.

Home in Windham

4.94 out of 5 average rating, 140 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 favorite

A wooden rocking chair is positioned near a window, featuring a soft yellow throw draped over the backrest. A round gray cushion rests on the seat, adding a touch of comfort and style to the inviting corner.

Guesthouse in Cumberland

4.96 out of 5 average rating, 115 reviews

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.

Top guest favorite

A quiet, tree-lined street is shown, with a blend of greenery from the surrounding foliage. American flags are displayed proudly on poles along the road, contributing to the serene atmosphere. The paved road leads deeper into the neighborhood, inviting exploration.

Apartment in Gray

4.95 out of 5 average rating, 143 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.

Guest favorite

A tranquil outdoor scene features a wooden pathway leading to the water's edge, surrounded by lush greenery and a tree. The two-story boathouse is partially visible, with steps guiding down to the dock and a serene lake reflecting the blue sky.

Guesthouse in New Gloucester

4.88 out of 5 average rating, 138 reviews

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Guest favorite

A wooden dock extends into calm waters, surrounded by lush greenery and trees along the shoreline. Smooth stones are visible along the water's edge, while the clear blue sky complements the tranquil setting. The dock features a ladder for easy access to the lake.

Cottage in Raymond

4.91 out of 5 average rating, 112 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Top guest favorite

A modern kitchen features white cabinetry and granite countertops. Stainless steel appliances, including an oven, microwave, and dishwasher, are arranged for convenience. Natural light enters through a window above the kitchen sink, illuminating the wood flooring and overall design.

Barn in Freeport

5 out of 5 average rating, 179 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Welcome to our spacious 1000 sq. ft. Maine barn apartment! 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 private 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

Superhost

A rustic bathroom features wooden walls and a carved sink made from natural materials. A mirror hangs above the sink, with decorative items displayed around it. Soft towels are neatly arranged on the countertop, contributing to a homey feel.

Cabin in Raymond

4.93 out of 5 average rating, 154 reviews

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.

Top guest favorite

A spiral staircase leads to a small loft area, while the kitchen features a gas range and a full-size refrigerator. The open layout allows for light to fill the spacious living area, which includes a sectional couch and a dining area with a table.

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.

Guest favorite

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, 213 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.

Top guest favorite

A charming home, framed by snow-covered trees, is gently illuminated by warm outdoor lights. The ground is blanketed in fresh snow, creating a serene atmosphere. The structure features a sloped roof and large windows, with inviting warmth visible from inside.

Home in Cumberland

4.95 out of 5 average rating, 300 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.

Guest favorite

A light-filled studio interior showcases a sitting area with a patterned sofa and wooden chairs, complemented by a dresser and small table. A fully equipped kitchen is visible, featuring a refrigerator and minimalist decor. Natural light enters through two windows, creating a serene ambiance.

Guesthouse in Cumberland

4.96 out of 5 average rating, 225 reviews

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.

Vacation rentals for every style

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Popular amenities for Gray vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Gray

Top guest favorite

A two-story farmhouse stands under a clear night sky filled with stars. The home is warmly lit, highlighting the entrance and porch area. A large tree is visible, adding to the rural ambiance. The surrounding area is dark, emphasizing the brightness of the house.

Apartment in New Gloucester

5 out of 5 average rating, 19 reviews

Cozy Winter Suite & Hot Tub

EmiliaRating, 5 stars6 days ago

Loved our stay! Owner answers quick, and is super easy to work with! The hot tub was a great place to relax, what a treat. Beautiful spot!

Top guest favorite

An open-concept living area showcases wooden walls and ceilings, creating a warm ambiance. A dining table with chairs sits beside a well-equipped kitchen, which includes a refrigerator and ample counter space. Comfortable seating is provided, with a wicker chair accentuating the cozy environment.

Home in Raymond

5 out of 5 average rating, 21 reviews

Cozy Cottage in Raymond

KeeraRating, 5 stars8 months ago

Alexis was very nice and welcoming, the house was clean and as described. We enjoyed our stay here very much.

Guest favorite

A sign indicating private beach access is displayed with bold green lettering. The sign emphasizes restrictions such as 'Keep Out', 'Only Members Allowed', and 'No Dogs Allowed', along with parking instructions. Snow partially covers the ground, creating a wintery scene.

Home in Raymond

4.91 out of 5 average rating, 43 reviews

Cottage with private beach access to sebago lake

JodiRating, 5 stars1 week ago

I stayed here solo for a weekend event just 10 minutes away, and it was the perfect home base. The listing matched the description to a T! The cottage is clean, cozy, and updated with care, featuring fresh paint, new furniture, and thoughtful touches throughout. Although it’s ideal for families or couples, it was also just right for a solo getaway. I kicked off the season with a lobster roll at the place down the street (because where else but Maine?), and enjoyed the peaceful vibe the whole weekend. The private little sand beach down the road is a lovely bonus—just a short walk and you're by beautiful Sebago Lake. It’s a great place to relax. The location is also super convenient—close to shopping, dining, and 10 minutes away from my event at St Joseph's College. Andy was a fantastic host, allowing me to check in early and making sure everything was easy. Honestly, if you forgot to pack something, chances are Andy already thought of it and had it stocked. Highly recommend!!

Guest favorite

An airy kitchen features a large island with dark granite countertops and seating for several. Light hangs from the ceiling, illuminating the wood-paneled walls and large windows that provide views of the surrounding greenery. A cozy living area is visible in the background.

Cottage in Gray

4.94 out of 5 average rating, 53 reviews

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!

Superhost

A circular stone patio features a built-in fire pit at its center. Surrounding the patio, lush greenery provides a natural backdrop. A picnic table is positioned nearby, offering a space for outdoor dining or relaxation.

Home in Gray

4.83 out of 5 average rating, 6 reviews

Little Sebago Lake with boat dock

KaitlinRating, 5 stars10 months ago

We had a great week at Ashley’s place! We used the kayaks several times and walked the trails nearby. House was very spacious and comfortable. Highly recommend!

Guest favorite

A private dock stretches over calm waters, providing direct access to Tripp Lake. The dock features a sturdy, metal frame and a textured surface for safety. Surrounding trees frame the serene view, enhancing the peaceful lake environment.

Cabin in Poland

4.86 out of 5 average rating, 43 reviews

Cozy cabin on the lake with the loons

AlleighRating, 5 stars1 month ago

This cabin is one of the most wonderful places I have been. My partner and I stayed just under a week and we enjoyed every second! It was so peaceful and relaxing to be away in such a beautiful home in an amazing area!

Guest favorite

A scenic view is presented from a small deck, featuring a grassy expanse and colorful autumn trees. A white mug rests on the railing, with a backdrop of a softly painted sky at dusk, enhancing the tranquil atmosphere of the location.

Apartment in Casco

4.93 out of 5 average rating, 45 reviews

Country Village Getaway

RyanRating, 5 stars1 week ago

Terri , Richard , and Daisy do a phenomenal job of being great hosts. Check in was smooth, and so well thought out. My friend and I were greeted with a hand written welcome sign and some local goodies from a nearby bakery which was absolutely unexpected but so appreciated after a long journey. The place is clean and cozy, with very thoughtful touches and details . Richard had some really great food spot recommendations and Daisy’s positivity was contagious. I look forward to visiting again and highly recommend this place if anyone is in the Casco area and looking for a quiet and cozy spot.

Guest favorite

A serene lakeside scene features three dark Adirondack chairs arranged around a small table on a wooden dock. The calm water reflects vibrant autumn foliage, creating a harmonious view of trees in shades of orange, yellow, and green against a partly cloudy sky.

Apartment in Windham

5 out of 5 average rating, 8 reviews

The Nest

DeborahRating, 5 stars6 days ago

Lovely stay while visiting Windham. Cute, cozy space with everything we needed. Beautiful grounds. Highly recommend.

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Quick stats about vacation rentals in Gray

Total rentals
100 properties
Total number of reviews
3.9K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
100 properties include access to wifi

Frequently Asked Questions

Are there pet-friendly vacation rentals in Gray?
Four-legged friends are welcome in Gray. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Gray?
Yes! Work meets play with ease at over 40 vacation rentals in Gray featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Gray have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Gray. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Gray?
Experience the best of Gray with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Gray have wireless internet?
Absolutely! We offer over 60 house rentals with wireless internet in Gray. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Gray have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Gray. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Gray?
Gray has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cottage Rentals in Gray?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Gray vacation rentals

Top-rated vacation rentals in Gray

Vacation rentals for every style

Popular amenities for Gray vacation rentals

Other great vacation rentals in Gray

Quick stats about vacation rentals in Gray

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

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