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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.

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: This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, ( 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.
$257 per night
Farm stay in Gray
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.
$158 per night
Guesthouse in Windham
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.
$125 per night

Stay near Gray's top sights

Maine Wildlife Park54 locals recommend
Pineland Farms66 locals recommend
Walmart Supercenter14 locals recommend
Hannaford Supermarket22 locals recommend
Cole Farms Restaurant & Pub3 locals recommend
Smitty's Cinema Windham25 locals recommend

Other great vacation rentals in Gray

Apartment in Freeport
Cozy Maine Barn Hideaway- 2nd Floor Apartment
$155 per night
Guesthouse in Cumberland
Cottage Under a Crabapple Tree
$75 per night
Tiny home in New Gloucester
Cedar Brook Cabin - a modern tiny house in Maine
$131 per night
Farm stay in Gray
Great Goat Get-away in Southern Maine!
$179 per night
Guesthouse in New Gloucester
On the water Boathouse!
$175 per night
Guest suite in Windham
Millers Private Studio on Highland Lake
$75 per night
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
$65 per night
Cottage in Portland
Cozy & Quiet Modern Cottage
$81 per night
Cottage in Gray
Sunset Haven - Little Sebago Lake
$225 per night
Home in Freeport
The Outlet House, Comfortable Cottage
$136 per night
Apartment in Westbrook
Studio Apt In Walkable Distance to Restaurants
$79 per night
Apartment in Portland
Self-check-in | Desk | Washer + Dryer | Kitchen 2
$80 per night

Quick stats about vacation rentals in Gray

Total rentals

90 properties

Wifi availability

90 properties include access to wifi

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

3.5K 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 40 vacation rentals in Gray featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cottage rentals in Gray have a bbq area?

    Absolutely! We offer over 10 cottage 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 50 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 House Rentals in Gray?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with a bbq area, over 30 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Gray