Gray vacation rentals

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Top-rated vacation rentals in Gray

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Guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 326 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.

Guest favorite

Tiny home in Durham

4.99 out of 5 average rating, 301 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 & chickens grazing in the fields.

Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 167 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Guest favorite

Cottage in Gray

4.9 out of 5 average rating, 191 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.

Superhost

Farm stay in Gray

4.88 out of 5 average rating, 246 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 280 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 family to stay and the rental is the entire home.

Guest favorite

Home in Lewiston

4.98 out of 5 average rating, 141 reviews

Clean and comfortable home

First floor of newly renovated, well-stocked, single-family home in quiet, safe neighborhood. Full kitchen, 2 bedrooms each with comfortable queen-sized bed, full bathroom, on-site laundry. Shoppable art on-site :) Located less than 1 mi from Bates College and St. Mary’s Hospital. Less than 2 mi from Central Maine Medical Center. Proof of Covid-19 vaccination may be requested for all eligible to receive vaccine (including children).

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 221 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.

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 152 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Guest favorite

Guesthouse in Cumberland

4.97 out of 5 average rating, 154 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.

Guest favorite

Guest suite in Lewiston

4.97 out of 5 average rating, 194 reviews

Sanctuary in the City

Welcome to our sanctuary in the city. Conveniently located just off the I-95, our spacious one-bedroom suite offers a queen bed, bath with cedar sauna, kitchenette, private yard with pergola, and laundry. Enjoy quick access to a range of local shops & restaurants, endless outdoor activities, and convenient access to Portland and Southern Maine’s coastal region.

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 249 reviews

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!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Gray vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Gray's top sights

Maine Wildlife Park54 locals recommend

Pineland Farms66 locals recommend

Walmart Supercenter14 locals recommend

Cole Farms Restaurant & Pub3 locals recommend

Smitty's Cinema Windham25 locals recommend

Hannaford Supermarket22 locals recommend

Other great vacation rentals in Gray

Guest favorite

Bus in Durham

4.93 out of 5 average rating, 115 reviews

Celebration Bus: Tree Farm & Wellness Center

Guest favorite

Guest suite in Cumberland

4.92 out of 5 average rating, 108 reviews

Springer Park! adorable guesthouse very stylish!

Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 196 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Guest favorite

Guest suite in Raymond, Maine

4.89 out of 5 average rating, 123 reviews

Rustic knotty pine getaway

Guest favorite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Superhost

Cottage in Raymond

4.92 out of 5 average rating, 99 reviews

Cozy Waterfront Cabin in Raymond

Guest favorite

Apartment in Gray

4.94 out of 5 average rating, 82 reviews

Two bedroom duplex across st from crystal lake

Guest favorite

Guest suite in New Gloucester

5.0 out of 5 average rating, 18 reviews

Many Moons Farm

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Other great vacation rentals in Gray

Guest favorite

Cabin in Windham

5.0 out of 5 average rating, 14 reviews

Cozy Private Lake Getaway (Seasonal)

Guest favorite

Cottage in Gray

4.94 out of 5 average rating, 34 reviews

Charming 3 bedroom cottage on Notched Pond

Guest favorite

Apartment in Casco

4.9 out of 5 average rating, 30 reviews

Country Village Getaway

Guest favorite

Home in Gray

4.95 out of 5 average rating, 43 reviews

cozy 3 bedroom ranch with deck and screen porch

Guest favorite

Camper/RV in New Gloucester

4.98 out of 5 average rating, 48 reviews

Joelsa Farm’s Camper

Guest favorite

Apartment in Windham

5.0 out of 5 average rating, 92 reviews

The Roost - lovely one bedroom efficiency unit

Guest favorite

Home in Cumberland

5.0 out of 5 average rating, 20 reviews

Tranquil Home on Nature Preserve

Guest favorite

Cottage in Windham

5.0 out of 5 average rating, 65 reviews

Romantic waterfront cottage for two in Maine

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Quick stats about vacation rentals in Gray

Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
3.3K reviews

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 50 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 40 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 house rentals in Gray?
Gray has more than 50 family-friendly house 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 a bbq area, over 10 homes with wireless internet, over 10 homes with air conditioning, 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

Houses

Hotels

Unique stays

Popular amenities for Gray vacation rentals

Stay near Gray's top sights

Other great vacation rentals in Gray

Bus in Durham

Guest suite in Cumberland

Apartment in Gorham

Guest suite in Raymond, Maine

Apartment in Freeport

Cottage in Raymond

Apartment in Gray

Guest suite in New Gloucester

Other great vacation rentals in Gray

Cabin in Windham

Cottage in Gray

Apartment in Casco

Home in Gray

Camper/RV in New Gloucester

Apartment in Windham

Home in Cumberland

Cottage in Windham

Quick stats about vacation rentals in Gray

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Gray?

Are there vacation rentals with a dedicated workspace in Gray?

Do house rentals in Gray have a bbq area?

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

Do house rentals in Gray have wireless internet?

Do cottage rentals in Gray have air conditioning?

Are there family-friendly house rentals in Gray?

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

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