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, 322 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.

Mar 3 – 10

G$57,243 GYD per night

Guest favorite

Bus in Durham

4.93 out of 5 average rating, 115 reviews

Celebration Bus: Tree Farm & Wellness Center

You could relax on a beautiful organic farm in Maine! Stay on our whimsical, comfortable, and surprisingly spacious bus, nestled in a secluded wooded area perched over a brook where you'll see a variety of wildlife. Explore beautiful walking trails that wind through blueberry & raspberry patches & the forest on our 110 acres. You may restore your body & soul through private yoga, Reiki, & wellness sessions. Eat delicious food from our harvest baskets of fresh vegetables & eggs from the farm.

Jun 17 – 24

G$19,643 GYD per night

Guest favorite

Tiny home in Durham

4.99 out of 5 average rating, 298 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.

Dec 28 – Jan 4

G$35,241 GYD per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 171 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

May 2 – 9

G$21,063 GYD per night

Guest favorite

Cottage in Gray

4.9 out of 5 average rating, 190 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.

Feb 5 – 12

G$53,888 GYD per night

Guest favorite

Farm stay in Gray

4.88 out of 5 average rating, 240 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.

Jul 10 – 17

G$35,913 GYD per night

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 279 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.

Mar 5 – 12

G$39,408 GYD per night

Guest favorite

Home in Lewiston

4.99 out of 5 average rating, 138 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).

Sep 17 – 24

G$24,941 GYD per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 217 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.

Jul 10 – 17

G$26,433 GYD per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 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.

Jun 13 – 20

G$24,049 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 195 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

G$14,547 GYD per night

Guest favorite

Guest suite in Lewiston

4.97 out of 5 average rating, 191 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.

Dec 1 – 8

G$28,504 GYD per night

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

Farm stay in North Yarmouth

4.96 out of 5 average rating, 111 reviews

Hobby Farm Guesthouse-17 acre trails-1 good dog OK

Dec 17 – 24

G$37,328 GYD per night

Guest favorite

Cabin in Raymond

4.93 out of 5 average rating, 144 reviews

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

Oct 7 – 14

G$38,352 GYD per night

Guest favorite

Tiny home in Windham

4.97 out of 5 average rating, 172 reviews

The Chickadee House on Pettingill Pond

Nov 10 – 17

G$35,571 GYD per night

Guest favorite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

May 25 – Jun 1

G$38,272 GYD per night

Guest favorite

Guesthouse in New Gloucester

4.89 out of 5 average rating, 107 reviews

On the water Boathouse!

Dec 26 – Jan 2

G$50,921 GYD per night

Superhost

Tiny home in New Gloucester

4.89 out of 5 average rating, 169 reviews

Cedar Brook Cabin - a modern tiny house in Maine

Jun 29 – Jul 6

G$68,236 GYD per night

Guest favorite

Apartment in Gray

4.96 out of 5 average rating, 26 reviews

A lovely 2 Bedroom Apt 1st FL w/ backyard and deck

Apr 23 – 30

G$23,867 GYD per night

Guest favorite

Guest suite in New Gloucester

5.0 out of 5 average rating, 13 reviews

Many Moons Farm

Aug 18 – 23

G$14,539 GYD per night

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Other great vacation rentals in Gray

Guest favorite

Home in Gray

4.95 out of 5 average rating, 43 reviews

cozy 3 bedroom ranch with deck and screen porch

Nov 4 – 11

G$48,996 GYD per night

Guest favorite

Apartment in Casco

4.9 out of 5 average rating, 30 reviews

Country Village Getaway

Mar 14 – 21

G$23,838 GYD per night

Guest favorite

Cabin in Windham

5.0 out of 5 average rating, 14 reviews

Cozy Private Lake Getaway (Seasonal)

Jul 12 – 17

G$38,722 GYD per night

Guest favorite

Camper/RV in New Gloucester

4.98 out of 5 average rating, 48 reviews

Joelsa Farm’s Camper

Feb 8 – 15

G$24,709 GYD per night

Guest favorite

Home in Cumberland

5.0 out of 5 average rating, 20 reviews

Tranquil Home on Nature Preserve

Jan 27 – Feb 3

G$84,931 GYD per night

Guest favorite

Guesthouse in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

Nov 4 – 11

G$26,973 GYD per night

Guest favorite

Guest suite in North Yarmouth

4.99 out of 5 average rating, 85 reviews

open concept Guest Suite in southern Maine

Feb 4 – 11

G$32,308 GYD per night

Guest favorite

Home in Gray

5.0 out of 5 average rating, 6 reviews

Cozy Lakefront Cottage on Little Sebago

Mar 1 – 8

G$91,903 GYD per night

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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 cottage rentals in Gray have wireless internet?
Absolutely! We offer over 10 cottage rentals with wireless internet in Gray. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gray have air conditioning?
Absolutely! We offer over 40 house 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 60 homes with wireless internet, over 40 homes with air conditioning, over 40 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

Houses

Hotels

Unique stays

Popular amenities for Gray vacation rentals

Stay near Gray's top sights

Other great vacation rentals in Gray

Farm stay in North Yarmouth

Cabin in Raymond

Tiny home in Windham

Apartment in Freeport

Guesthouse in New Gloucester

Tiny home in New Gloucester

Apartment in Gray

Guest suite in New Gloucester

Other great vacation rentals in Gray

Home in Gray

Apartment in Casco

Cabin in Windham

Camper/RV in New Gloucester

Home in Cumberland

Guesthouse in Freeport

Guest suite in North Yarmouth

Home in Gray

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 cottage rentals in Gray have wireless internet?

Do house rentals in Gray have air conditioning?

Are there family-friendly cottage rentals in Gray?

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

Destinations to explore