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Check availability on Great Diamond Island Historic Hotels

Top Great Diamond Island Historic Hotels

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Relax in this stylish living room with a flat-screen TV, comfortable sofa, and decorative vase.

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

10.0 out of 10, Exceptional, (23)
" Very spacious, clean and beautiful."
The price is £408
includes taxes & fees
10 Aug - 11 Aug
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Escape to a serene forest retreat with a spacious deck and covered porch.

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (18)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
The price is £780
includes taxes & fees
21 Jul - 22 Jul
Waterfront Spacious Luxury Home, 5 min to LL Bean!
The James Place Inn B&B
Enjoy a romantic meal for two on the deck, surrounded by the house's charming facade.

The James Place Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (172)
"Location to the busy areas of Freeport is steps away from this quiet oasis. Very nice innkeepers and staff will be there to make your stay pleasant while allowing you the privacy of a hotel guest. We stayed one night on our way home from mid coastal Maine and enjoyed our stay. "
The price is £245
includes taxes & fees
14 Jul - 15 Jul
The James Place Inn B&B
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Situated on a rocky shoreline, this house offers a scenic view of the surrounding forest and water.

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

9.8 out of 10, Exceptional, (31)
"I spent summers on Long Island in Casco Bay always dreaming of staying at Peak’s Island to see what all the hype was about… Well, it exceeded my expectations at this location! The communication with the owner, to the comfort of the cottage and view was priceless. We are already planning for next summer 😃"
The price is £954
includes taxes & fees
4 Aug - 5 Aug
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Penthouse Two Master Waterfront Suite with Rooftop
Enjoy the city's diverse architecture from the comfort of your room.

Penthouse Two Master Waterfront Suite with Rooftop

10.0 out of 10, Exceptional, (245)
"Enjoyed our 2nd stay..great location "
The price is £940
includes taxes & fees
4 Aug - 5 Aug
Penthouse Two Master Waterfront Suite with Rooftop
Glorious getaway on Portland's Eastern Promenade.
Stroll down this charming traditional street lined with historic buildings.

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (153)
"Gorgeous, cozy VRBO stocked with everything we needed. Hosts were so kind and accommodating. One of the best rental home experiences I’ve had. Definitely recommend!"
The price is £431
includes taxes & fees
4 Aug - 5 Aug
Glorious getaway on Portland's Eastern Promenade.
Adorable Portland getaway on the Eastern Promenade
Enjoy a panoramic view of the city from this corner room with large windows and a high ceiling.

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (103)
"The property was very nice and clean. Didn’t have any issues while there. Looking forward to another stay here next time I come to Portland. "
The price is £230
includes taxes & fees
15 Jul - 16 Jul
Adorable Portland getaway on the Eastern Promenade
Portland Regency Hotel & Spa
Relax in a stylish outdoor seating area with a wicker sofa and glass table, surrounded by a stone pathway and lush greenery.

Portland Regency Hotel & Spa

3.5 star property
9.4 out of 10, Exceptional, (1343)
"Great location and very friendly staff"
Portland Regency Hotel & Spa
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, oven, and microwave.

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

8.8 out of 10, Excellent, (30)
"Great place, a little difficulty controlling temperature."
The price is £299
includes taxes & fees
15 Jul - 16 Jul
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Elegant condo - walk to Portland's best restaurants & Old Port
Enjoy cooking in this well-lit kitchen with ample counter space and a large window offering a view of the outdoors.

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

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is £341
includes taxes & fees
28 Jul - 29 Jul
Elegant condo - walk to Portland's best restaurants & Old Port
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.