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Compare 457 Vacation Homes in Gray with updated reviews, rates, and availability.

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (111)
"We were two couples (in our 60’s) in Portland for a couple days visiting. John’s place was wonderful! We had plenty of space for the four of us with room to spare. Very comfortable and relaxing. We absolutely LOVED the front porch/deck. Very spacious and an amazing view of the beach and ocean! Bathroom and kitchen were not “updated” but it’s a 110 year old home so we really didn’t mind - everything worked and that’s what’s important. The apartment is upstairs and John lives downstairs. ...
Charming 110-year former Inn 10' from the Ocean!

Luxurious Penthouse with Modern Design in Downtown

9.2 out of 10, Wonderful, (5)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

Enchanting 3BR Farmhouse Retreat Nature Getaway

8.6 out of 10, Excellent, (10)
"If you need a place to stay in your way to Boston or Acadia, this will work fine. It was clean and newly remodeled. The host is very quickly responsive, but unfortunately was not able to answer our questions. The house has limited cooking supplies and dishes, and wash cloths were not provided. Overall, it was fine for passing through, but not well stocked or ready for an extended stay. "
Enchanting 3BR Farmhouse Retreat Nature Getaway

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

Full sized home

9.6 out of 10, Exceptional, (22)
"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."
The price is AED 826
AED 1,361 total
includes taxes & fees
25 Nov - 26 Nov
Full sized home

Oceanside escape 🌊 perfect family getaway!

9.8 out of 10, Exceptional, (10)
"Beautiful home! Well kept, clean and very comfortable. A little touch of history in this wonderful house and neighborhood. Great location, quick to Portland and the airport. We loved it!!!! Owner communication is a 10+++. "
Oceanside escape 🌊 perfect family getaway!

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

10.0 out of 10, Exceptional, (3)
"House was great, location was perfect and the local property manager was very responsive and helpful. "
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is AED 613
AED 1,564 total
includes taxes & fees
1 Dec - 2 Dec
Elegant condo - walk to Portland's best restaurants & Old Port

Rent a room in the gorgeous Holt House

8.2 out of 10, Very Good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House

Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK

8.6 out of 10, Excellent, (12)
"This is owners first year renting. It needs a complete review by electrician because there are several outlets not working. We also had trouble with the thermostats and heat. So that needs help too. The 1800 salt box portion of the home was charming to us. The addition added a great number of beds and baths. The kitchen was marginally stocked with bowls, etc so bring your own.. kitchen could have been cleaner too. So not smooth sailing but a comfy no fuss second home"
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

9.6 out of 10, Exceptional, (33)
"The house we stayed in was wonderful. It met all of our expectations. I highly recommend it!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (134)
"This property is fantastic and I would prioritize staying there each and every time I visit Portland."
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

☼ Maine Lakefront Getaway ☼

9.6 out of 10, Exceptional, (63)
"Traveled from New Mexico to visit with my son. I was looking for a place which would be near my son's residence giving us a centralized place to meet. It was just a few minutes away from my son's residence. House served all our needs and was clean and neat. Beautiful views from windows and deck. Will definitely stay again!!!"
☼ Maine Lakefront Getaway ☼

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.8 out of 10, Exceptional, (59)
"Comfortable, peaceful. Everything we needed for mussels, steamers and lobster Nice to have working dock in front of us for lobsters"
Beautiful house on the Harpswell Peninsula over looking Casco Bay

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

9.8 out of 10, Exceptional, (174)
"Great house, big enough for our family group ranging from 1 year old to 70 year old. :) Home was clean & spacious & cozy - with a beautiful view. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Back yard paradise

9.8 out of 10, Exceptional, (19)
"I live in California, but my son was married in Portland (our home state). We spent a long weekend close to family and wedding activities. This is a comfortable home, in a great location. I feel fortunate to have chosen the perfect VRBO."
Back yard paradise

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

NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

10.0 out of 10, Exceptional, (48)
"Spacious and and private! My family always enjoys their visit to Maine but this home and the property really made this visit special. Communication throughout the booking and reservation was easy and all of our questions were answered promptly. Thank you!"
NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

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

Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

8.0 out of 10, Very Good, (5)
"Daughter lives in area it suited us just fine."
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!
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.
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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, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
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, (99)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is AED 826
AED 1,922 total
includes taxes & fees
24 Nov - 25 Nov
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.