Photo by Deb Soromenho

Holiday Homes in Gray

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Gray

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (175)
"We all had a great time staying here. It was so clean and spacious and comfortable. Beautiful views. Easy in and out. We will come back again if we are coming back this way. Loved it!! Very relaxing. Thank you for a great weekend away!!"
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Modern, Luxury Lakefront Home on Crescent Lake, Maine

10.0 out of 10, Exceptional, (103)
"Well equipped and well maintained, very comfortable and peaceful. We had a great stay!"
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Lofty cottage

9.4 out of 10, Exceptional, (39)
"We really enjoyed our time here has a beautiful view of the ocean. Had all the things needed to kayak and go out on the water. Nice and secluded. Had a fire pit, which was lovely to turn on In the evening. Would recommend this place and stay again"
Lofty cottage

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
Charming ocean-view cottage just 10 minutes from downtown Freeport shops

Fully renovated home with lake view, dock & mooring access, kayaks, & deck

9.6 out of 10, Exceptional, (31)
"Lovely all around. Trees do obstruct view of lake some but still beautiful"
Fully renovated home with lake view, dock & mooring access, kayaks, & deck

Lakefront Cottage with Private Beach

9.8 out of 10, Exceptional, (26)
"We stayed during the Thanksgiving week and had an exceptional time. We had awesome communication with the property manager before and during the stay. We received snow during our stay, there were salt and sand buckets for our use and they came to shovel early in the morning. Very spacious, well furnished especially the kitchen. "
Lakefront Cottage with Private Beach

3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

8.4 out of 10, Very good, (6)
"We booked Nick’s place for myself, husband, 3 year old & my in-laws before we all left Portland. We were able to get an early check in, which was great because I felt horrible with a migraine & the heat was unbearable. The home has a lot of character. I would stay there again!"
The price is AU$1,042
includes taxes & fees
3 Dec - 4 Dec
3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

Rise & Shine on Sebago Lake

9.8 out of 10, Exceptional, (8)
"We wanted a place for extended family to be together for a family wedding at Caswell Farms There was room for everyone and a wonderful Lake Sebago view from multiple rooms We enjoyed kayaking, hot tub, wonderful kitchen amenities for a lobster boil Conveniently located to stores and restaurants Wonderful home and memories made!! Attentive hosts and maintenance staff Loved it!"
Rise & Shine on Sebago Lake

Shady Potts Point Cottage Cooled by Ocean Breezes

9.6 out of 10, Exceptional, (77)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes

Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

10.0 out of 10, Exceptional, (23)
"My family of three really enjoyed our stay! My 5 year old enjoyed playing with the different toys and puzzles at the house. Photos are accurate and the beds were very comfortable. The kitchen was well stocked for making meals. My son liked having his own room and bathroom upstairs. We spent a lot of time outside and had several fires! Visited Pineland Farms (loved seeing the cows up close!) and the Maine Wildlife Park (1000 ft from the house). Also loved that it was dog friendly so our pup...
Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

"Loon Cottage" on Sand Pond

10.0 out of 10, Exceptional, (3)
"The cabin was very clean when we arrived. The beds were very comfortable. The cabin has everything you need including many things in the kitchen to make meals if you want to. Towels, sheets, blankets, and swim towels were also provided. We enjoyed using the paddle boards and paddle boats. The pond was great for swimming and boating. The cabin has windows on all sides so we enjoyed lots of fresh air. It was also very quiet, restful, and peaceful on the pond. "
"Loon Cottage" on Sand Pond

Point Sebago Gated Golf & Beach Community

10.0 out of 10, Exceptional, (3)
"The house was clean and well appointed. We would definitely stay here again!"
Point Sebago Gated Golf & Beach Community

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10

9.6 out of 10, Exceptional, (7)
"Cute place with nice amenities. Friendly and responsive host. Love Peak's Island! Nice relaxing location. Great for walking and biking."
New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10

Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell

2.0 star property
9.6 out of 10, Exceptional, (11)
"We very much enjoyed our stay at the Blue Lobster! We were in town visiting our student at Bowdoin and found this property to be a lovely vacation spot a reasonable distance from campus. The house sits on a beautiful spot on the water and had everything we needed for our stay. We will return!"
Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell

Modern Comfort: Game Room & Access to Portland

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very nice."
Modern Comfort: Game Room & Access to Portland

Serenity between the lakes and seashore

9.8 out of 10, Exceptional, (15)
"Good location near lots of hiking and not far from Portland "
The price is AU$442
includes taxes & fees
13 Dec - 14 Dec
Serenity between the lakes and seashore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Gray
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Gray

Sensational House on Sebago Lake, Raymond, ME

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (36)
"Beautiful place , had everything you need . Very comfortable bed . Great shower & Kitchen . Also a great location! "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (100)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is AU$814
includes taxes & fees
3 Dec - 4 Dec
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.