Photo by Deb Soromenho

Gray Holiday Rentals

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Holiday Rentals 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

Cozy, Elegant and Bright 2 bed in the East End

9.6 out of 10, Exceptional, (35)
"Fabulous location for us as it’s just 1/2 block from our son’s apartment. So close to Casco Bay and the Portland Port area. Walkable to restaurants and shopping. Nice sunny apartment! "
The price is AU$565
includes taxes & fees
3 Dec - 4 Dec
Cozy, Elegant and Bright 2 bed in the East End

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

Lakefront home with lovely lake views - one mile from the casino

9.8 out of 10, Exceptional, (41)
"This was the perfect location to get away for the weekend and celebrate my wife and I’s 10 year anniversary. The property was clean, private, and had great views being on the pond. The hot tub was an added bonus. I would definitely recommend this home and stay here again! "
Lakefront home with lovely lake views - one mile from the casino

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

9.0 out of 10, Wonderful, (27)
"Cute place - makes very good use of the space. It was comfortable and very conveniently located to everything we wanted to do. We have a few suggestions but overall very happy, had a wonderful time, and the ultimate compliment - we look forward to staying there again. "
The price is AU$595
includes taxes & fees
3 Dec - 4 Dec
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

8.0 out of 10, Very good, (15)
"We loved the cottage, moved in very late day so didn’t notice the floors till sunny next morning…..the floors had never been vacuumed. Other than that, we really liked the cottage."
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

Romantic getaway for two Thanksgiving at Trickey pond early check in

10.0 out of 10, Exceptional, (291)
"A lovely conferable place"
Romantic getaway for two Thanksgiving at Trickey pond early check in

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 AU$649
includes taxes & fees
3 Dec - 4 Dec
Elegant condo - walk to Portland's best restaurants & Old Port

Beautiful oceanside Castle with private beach and seasonal swimming pool

10.0 out of 10, Exceptional, (35)
"It was a wonderful home for a birthday celebration with friends that wanted to experience Maine. The grounds were expansive with lovely water views. The host were very responsive."
Beautiful oceanside Castle with private beach and seasonal swimming pool

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

9.8 out of 10, Exceptional, (113)
"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!

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

8.6 out of 10, Excellent, (35)
"We would absolutely book this house again. Super peaceful location. Loons in the morning were a stellar start to each day. "
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (140)
"Excellent location and very clean apartment"
The price is AU$479
includes taxes & fees
9 Dec - 10 Dec
Glorious getaway on Portland's Eastern Promenade.

Rent a room in the gorgeous Holt House

8.2 out of 10, Very good, (22)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House

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

The Globe House on Munjoy Hill - Walk to Breweries - monthly Dec-May

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries - monthly Dec-May

Lakefront House

10.0 out of 10, Exceptional, (21)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is AU$1,258
includes taxes & fees
3 Dec - 4 Dec
Lakefront House

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!
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 types of properties in Gray you may be interested in

La Quinta Inn & Suites by Wyndham Portland

2.5 star property
9.0 out of 10, Wonderful, (2043)
"Think was a last minute stay, but our room was very clean and quiet. Great breakfast as well. "
The price is AU$140
includes taxes & fees
4 Dec - 5 Dec
La Quinta Inn & Suites by Wyndham Portland

Casco Bay Hotel, Ascend Hotel Collection

3.5 star property
8.4 out of 10, Very good, (2388)
"Clean and economical, fairly modern, “lite” breakfast, but plenty of local options for dining or fast food. I have recommended it to family with no regrets. It is our PWM goto…."
The price is AU$119
includes taxes & fees
16 Dec - 17 Dec
Casco Bay Hotel, Ascend Hotel Collection

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1422)
"Great hotel, second stay and would come again!"
The price is AU$271
includes taxes & fees
4 Dec - 5 Dec
Portland Harbor Hotel
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.

Frequently asked questions

Are there holiday rentals in Gray?

Yes, there are holiday rentals close to the most popular sights in Gray, or you can select a more secluded option if you're looking for a relaxing stay. Gray is known for its shopping and golf courses.

What are some of the best holiday rentals that Gray has to offer?

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This holiday home rental outside of Gray is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals will I find in Gray?

Choose from 16 Expedia holiday rentals in Gray for a memorable holiday.

What’s there to see and do in Gray?

While exploring the area, visit family-friendly sights like Bayside Bowl, or get outside and enjoy nature at Little Sebago Lake. Spring Meadows Golf Course and St Josephs College are a couple of places you'll find in the wider area.

What’s a holiday rental in Gray like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gray. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.