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Compare 600 Vacation Homes in Gray with updated reviews, rates, and availability.

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very Good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (77)
"Great historic house in a terrific location. "
The Globe House on Munjoy Hill - Walk to Breweries

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"We had a great stay! Amazing weather and plenty of lobster."
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.8 out of 10, Exceptional, (12)
"We loved everything about this place. Beautiful, large home, plenty of room for 8 adults and 2 children. Large dining room for meals and family game time. So close to Freeport and all the shopping. Very clean, and the home has everything we needed. We can’t wait to go again!"
The price is SAR 544
SAR 1,587 total
includes taxes & fees
13 May - 14 May
Spacious Country Home Freeport, Only 5 min to LL Bean!

Beautiful House just a step from ocean

9.0 out of 10, Wonderful, (2)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful House just a step from ocean

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

9.4 out of 10, Exceptional, (60)
"Great location, walkable to everything we wanted to do in Portland"
The price is SAR 600
SAR 1,615 total
includes taxes & fees
13 May - 14 May
Elegant condo - walk to Portland's best restaurants & Old Port

Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very Good, (3)
"It was very convenient. "
The price is SAR 676
SAR 2,013 total
includes taxes & fees
13 May - 14 May
Prime City Living Townhouse by RedAwning

Full sized home

9.8 out of 10, Exceptional, (26)
"This property was as described and it felt like we were staying at a family member’s cozy house. The towels were thick, the beds were comfortable, and the kitchen had everything we needed."
The price is SAR 844
SAR 1,402 total
includes taxes & fees
14 May - 15 May
Full sized home

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.8 out of 10, Exceptional, (59)
"We had our wedding party stay at this property for our wedding at live well farm. It was beautiful and everyone enjoyed their stay. "
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Welcome to Happy Place on Peaks Island

10.0 out of 10, Exceptional, (39)
"Lovely cottage."
Welcome to Happy Place on Peaks Island

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (21)
"The reclining furniture was our favorite after running around all day! Very comfortable beds! Great place to stay!"
Convenient Portland home 3 miles from Downtown

Huge Historic Downtown Townhome

10.0 out of 10, Exceptional, (1)
"From California, I put together a 21st birthday weekend in Portland for my daughter and five of her friends from Bates College. Tim, the manager, was communicative, helpful, and always available. The townhome is adorable, and the location is fantastic."
The price is SAR 911
SAR 1,627 total
includes taxes & fees
13 May - 14 May
Huge Historic Downtown Townhome

Cozy four-season getaway on Pettingill Pond

Cozy four-season getaway on Pettingill Pond

Luxurious Penthouse with Modern Design in Downtown

9.6 out of 10, Exceptional, (7)
"We had an amazing stay and it was an immense pleasure to call this charming place homebase for a long weekend during the holidays and a family wedding! Many thanks to the owners for hosting us!!"
Luxurious Penthouse with Modern Design in Downtown

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

9.8 out of 10, Exceptional, (178)
"What a beautiful home and location! Second time we have stayed here and love it. "
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Sunrise Catcher with a Panoramic View!

10.0 out of 10, Exceptional, (39)
"A wonderful location and super comfortable accommodations"
Sunrise Catcher with a Panoramic View!

Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres

10.0 out of 10, Exceptional, (15)
"This house is beautifully designed and ideal for a family vacation. We had a wonderful stay, and Jocelyn, our host, made everything easy to navigate, always being available for any questions we had. "
Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres

Our Happy Place on the Lake

Our Happy Place on the Lake
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

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (58)
"Great hotel"
The price is SAR 928
SAR 1,293 total
includes taxes & fees
13 May - 14 May
The Weldon Hotel

Cozy Maine cabin nestled in the woods, dog-friendly

10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at Bowhaven cabin! It was extremely clean—truly spotless—and clearly very well cared for. Kez and Kyle are wonderful hosts: super communicative, welcoming, and thoughtful from start to finish. You can tell they take great pride in the property. The setting is peaceful and cozy, and everything we needed was right there. I’m already looking forward to coming back. Highly recommend!"
The price is SAR 375
SAR 593 total
includes taxes & fees
21 May - 22 May
Cozy Maine cabin nestled in the woods, dog-friendly

Completely remodeled 2 bedroom apartment in Portland's West End

10.0 out of 10, Exceptional, (60)
"This was a great place for our family to relax and enjoy Portland. There are so many places to eat nearby and the reserved parking was much appreciated."
The price is SAR 844
SAR 1,684 total
includes taxes & fees
15 May - 16 May
Completely remodeled 2 bedroom apartment in Portland's West End
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.