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Holiday Homes in Great Island

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Great Island holiday homes

Terrace/patio
Camp Forever cottage

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is €317
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage
Property grounds
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (7)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is €362
includes taxes & fees
23 Dec - 24 Dec
Orchid Harbor, Bailey Island 3BR
Living area
Escape to Positive Outlook

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €176
includes taxes & fees
15 Dec - 16 Dec
Escape to Positive Outlook
Interior
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is €139
includes taxes & fees
15 Dec - 16 Dec
The Outlet Studio, Rustic Comfort w Fireplace
Outdoor dining
Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is €394
includes taxes & fees
16 Dec - 17 Dec
Mere Point Sunrise Views at Eastern Shore!
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
" Views were amazing. Host was perfect. 5 of us were very comfortable there. Loved the area. "
United States
Viki P.
The price is €325
includes taxes & fees
5 Jan - 6 Jan 2026
Fantastic Waterfront Views
Interior
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is €333
includes taxes & fees
15 Dec - 16 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Property grounds
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming
South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is €421
includes taxes & fees
14 Dec - 15 Dec
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Fridge, microwave, oven, stovetop
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
United States
David H.
The price is €600
includes taxes & fees
15 Dec - 16 Dec
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Smart TV
Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach
Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is €506
includes taxes & fees
21 Dec - 22 Dec
Laughton House @ Pemaquid Beach
Interior
Modern Getaway by the Sea

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is €387
includes taxes & fees
14 Dec - 15 Dec
Modern Getaway by the Sea
Outdoor dining
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (37)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €289
includes taxes & fees
14 Dec - 15 Dec
Modern & Sunny House Steps from the Promenade. Private Parking!
Interior
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
2.0 star property
Brunswick
The price is €392
includes taxes & fees
13 Jan - 14 Jan 2026
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Interior
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is €273
includes taxes & fees
14 Dec - 15 Dec
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Smart TV
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is €311
includes taxes & fees
21 Dec - 22 Dec
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Smart TV
Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home
Topsham
The price is €454
includes taxes & fees
15 Dec - 16 Dec
Generous Living in a Warm, Welcoming Home
1 bedroom, Internet, bed sheets
Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is €199
includes taxes & fees
14 Dec - 15 Dec
Charming 1-bedroom ADU in wonderful Portland neighborhood
Beach
Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (2)
"This was a last minute booking for our family as we had a basketball tournament, there were 8 of us including 3 children. This was the most kid friendly house we have stayed in! It was so well stocked for the entire family. The house was meticulously cleaned and the hosts were very responsive to any questions! "
United States
Melissa L.
The price is €596
includes taxes & fees
14 Dec - 15 Dec
Pemaquid Escape | Curated Comfort + Hot Tub
Property grounds
Classic New England Waterfront

Classic New England Waterfront

Classic New England Waterfront
Harpswell
10.0 out of 10, Exceptional, (2)
"Great property"
United States
Scott D.
The price is €619
includes taxes & fees
14 Dec - 15 Dec
Classic New England Waterfront
Microwave, oven, stovetop, dishwasher
The Barnhouse with hot tub

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (6)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is €310
includes taxes & fees
25 Dec - 26 Dec
The Barnhouse with hot tub
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities. "
Heidi 1-night trip
Posted 1 day ago
Portland Harbor Hotel

Find out more about Great Island

Great Island Holiday Homes information

Number of reviews
255
Accommodation
583 Holiday Homes
Lowest Price
€139
Highest Price
€619

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