A coastal landscape with a sandy beach, dense forest, and a bay surrounded by hills.

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Our top choices for Great Island vacation homes

1. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is ¥27,282
¥64,223 total
includes taxes & fees
Nov 16 - Nov 17
Orchid Harbor, Bailey Island 3BR

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is ¥16,591
¥32,346 total
includes taxes & fees
Nov 16 - Nov 17
Mid Coast Getaway w/ water views

3. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is ¥17,051
¥54,163 total
includes taxes & fees
Nov 11 - Nov 12
Quiet Spot in lovely Freeport neighborhood

4. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is ¥18,961
¥28,073 total
includes taxes & fees
Nov 24 - Nov 25
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

5. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is ¥20,541
¥29,796 total
includes taxes & fees
Nov 30 - Dec 1
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is ¥19,841
¥55,749 total
includes taxes & fees
Nov 16 - Nov 17
Mere Point Sunrise Views at Eastern Shore!

7. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is ¥22,595
¥72,853 total
includes taxes & fees
Nov 11 - Nov 12
Fully Updated Airy Historic Home in South Freeport

8. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is ¥20,739
¥35,834 total
includes taxes & fees
Nov 17 - Nov 18
2 bedroom w/ expansive water views

9. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
8.8 out of 10, Excellent, (3 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is ¥24,334
¥43,580 total
includes taxes & fees
Nov 15 - Nov 16
Captains Watch: A Coastal Escape

10. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
The price is ¥26,072
¥63,037 total
includes taxes & fees
Dec 1 - Dec 2
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

11. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.4 out of 10, Exceptional, (3 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is ¥21,655
¥100,648 total
includes taxes & fees
Nov 17 - Nov 18
Charming Historic home steps away from downtown

12. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is ¥55,304
¥240,779 total
includes taxes & fees
Nov 30 - Dec 1
Classic New England Waterfront House Big Lawn Beautiful Sunrise

13. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ¥24,887
¥42,755 total
includes taxes & fees
Nov 11 - Nov 12
Fantastic Waterfront Views

14. Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (14 reviews)
"Another great stay by a great host. The host Jared even provided some activities for our granddaughters to do while we were on vacation. You will not be disappointed with this property. Looking to stay there again in the future. Thank you, Jared!"
United States
Ronald H.
The price is ¥47,245
¥71,648 total
includes taxes & fees
Nov 15 - Nov 16
Award Winning Luxury Carriage House a short stroll from town!

15. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ¥31,602
¥52,703 total
includes taxes & fees
Nov 30 - Dec 1
Full sized home

16. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"The house was amazing. We would recommend this property to anyone. The view, stars at night and accessibility to where we wanted to visit, was perfect."
United States
Vanessa K.
The price is ¥51,606
¥126,520 total
includes taxes & fees
Nov 12 - Nov 13
Casco Bay Oceanfront Retreat by Everrow

17. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is ¥77,409
¥149,823 total
includes taxes & fees
Nov 16 - Nov 17
Heated Game Room, Coastal Maine Cape Sleeps 10

18. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (5 reviews)
"Great location and super clean house"
United States
Gary R.
The price is ¥38,712
¥111,261 total
includes taxes & fees
Nov 11 - Nov 12
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

19. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is ¥33,277
¥59,883 total
includes taxes & fees
Dec 10 - Dec 11
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

20. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (5 reviews)
"This cottage is the perfect blend of historic charm and modern upgrades. The view of the river is incredible, and the secluded location is just a short drive from downtown Wiscasset and Edgecomb. The sunroom is already a great place to hang out and enjoy the river view, but the owners are also putting in a lot of work to create an enjoyable outdoor space. Jeffrey is easy to work with and honestly wants you to have a good stay."
United States
Shelly
The price is ¥27,178
¥53,807 total
includes taxes & fees
Nov 11 - Nov 12
1920s Riverfront Cottage – Historic Maine Charm
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 Island Hotel Reviews

Find out more about Great Island

Great Island Vacation Homes information

Number of reviews
277
Accommodation
667 Vacation Homes
Lowest Price
¥28,073
Highest Price
¥240,779

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