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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Cottages in Great Diamond Island

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Relax on the deck with a comfortable sofa set and enjoy the serene lake view.

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Stroll through the charming garden, featuring a tree with vibrant foliage and a wooden bench on the covered porch.

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (39)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Relax in a serene outdoor setting with Adirondack chairs and a table overlooking the distant shoreline.

Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings

9.6 out of 10, Exceptional, (49)
"We had a wonderful time at this house! It’s perfectly situated by the beach, just a stone’s throw away from the charming village of Biddeford Pool. You can even grab some fresh, steamed lobster at the grocery store there. The house offers breathtaking views of the sunset and the bay, and there’s plenty of great outdoor space for relaxation. Parking is also a breeze. The host is incredibly friendly and responsive, making our stay even more enjoyable. We even had a travel massage for our...
Bright Beach Cottage, Waterviews, Dog Ok, Honeymoon, Weddings
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
Enjoy a peaceful retreat on this single-story home's deck, surrounded by lush trees and a clear sky.

Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access

9.6 out of 10, Exceptional, (4)
"This was a gem, and the location was perfect for what we need. Very charming and such a comfortable bed"
Loon Call Cottage DIRECTLY ACROSS from Little Sebago Lake With Easy Water Access
WATERFRONT ON PETTENGILL POND
Escape to a serene retreat surrounded by lush greenery and a tranquil stream.

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
Little Miss Cottages
Stroll up to this charming home, featuring a cozy front porch surrounded by a lush garden and a beautifully maintained lawn.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very Good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (4)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Large 2BD cottage 10 min to Pier & Beach Pets ok
Stroll up to the charming entrance, where a front porch invites you to relax.

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (33)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is ￥25,711
￥45,320 total
includes taxes & fees
Sep 3 - Sep 4
Large 2BD cottage 10 min to Pier & Beach Pets ok
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Enjoy the ocean views from this deck overlooking the coastline.

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Situated in a suburban setting, this two-story home features a curved balcony and a mix of siding materials.

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (46)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Relax on the deck with a tranquil view of the water, featuring a table, Adirondack chairs, and a shaded area.

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Quaint Cottage Just Steps From The Beach And The Saco River
Traditional two-story house with a charming porch and American flag.

Quaint Cottage Just Steps From The Beach And The Saco River

9.8 out of 10, Exceptional, (16)
"We had a very nice, clean and comfortable stay!"
Quaint Cottage Just Steps From The Beach And The Saco River
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Relax on the dockside deck, surrounded by lush greenery and picturesque views of the marina.

'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!

10.0 out of 10, Exceptional, (12)
"Really enjoyed the house and location."
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Enjoy serene lakeside views from the deck, surrounded by blooming flowers and trees.

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Enjoy a serene garden oasis with lush plants, a hedge, and a small tree, surrounded by a stone wall and outdoor dining area.

15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit

9.8 out of 10, Exceptional, (51)
"Convenient to all that Old Orchard Beach has to offer. Great communication and offerings of beach chairs and beach towels. Wonderful time. Definitely recommend."
15A Great Location! 5 min Walk to Beach/Pier-Cottage Sleeps 6;12 w/back unit
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
Relax on the waterfront deck with a barbecue grill and comfortable seating for two.

Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home

9.6 out of 10, Exceptional, (23)
"Very fun with beautiful views hoping to come back soon!"
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
2 bedroom cottage
Cozy living space with a kitchenette, sofa, dining table, and bench.

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
The Hidden Cove by Bayley Vacation Rentals
Enjoy a home away from home with a front porch, covered patio, and convenient parking.

The Hidden Cove by Bayley Vacation Rentals

9.8 out of 10, Exceptional, (22)
"Great stay"
The Hidden Cove by Bayley Vacation Rentals
Cute 2+ Bedroom Cottage
Situated in a serene wooded area, this cabin offers a peaceful retreat with a well-maintained lawn and an entrance.

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (18)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
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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Top Great Diamond Island Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

10/10 Excellent
"It’s really nice. Clean, staff is kind. A comfortable stay. "
Shoshana 1-night trip
Posted 23 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Frequently asked questions

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