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Great Island Holiday Rentals

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Our top choices for Great Island holiday rentals

Holiday Home in Harpswell

Camp Forever cottage
9.6 out of 10, Exceptional, (58)
"yes, nice view from backyard , fairly quiet spot , lots to do in the area , hikes , restaurants. "
United States
michael z.
The price is NZ$577
includes taxes & fees
31 Dec - 1 Jan 2026
Camp Forever cottage

Holiday Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (9)
"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 NZ$840
includes taxes & fees
2 Jan - 3 Jan 2026
Orchid Harbor, Bailey Island 3BR

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$410
includes taxes & fees
4 Jan - 5 Jan 2026
The Weldon Hotel
10.0 out of 10, Exceptional, (145)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is NZ$205
includes taxes & fees
30 Dec - 31 Dec
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (25)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$344
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny Spot with Private Parking.
10.0 out of 10, Exceptional, (1)
The price is NZ$613
includes taxes & fees
11 Jan - 12 Jan 2026
Large, luxurious geodesic dome - 04
10.0 out of 10, Exceptional, (8)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is NZ$379
includes taxes & fees
4 Jan - 5 Jan 2026
Modern style in historic building in downtown Bath
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is NZ$347
includes taxes & fees
5 Jan - 6 Jan 2026
Adorable Portland getaway on the Eastern Promenade

Holiday Home in West Point

Escape to Positive Outlook
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 NZ$325
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Apartment in Brunswick

Little Lincoln beautiful home
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is NZ$441
includes taxes & fees
25 Jan - 26 Jan 2026
Little Lincoln beautiful home
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$272
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 1st Floor Apartment & Amazing Shower
8.4 out of 10, Very good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is NZ$231
includes taxes & fees
30 Dec - 31 Dec
Studio Apartment near downtown Walkable!
10.0 out of 10, Exceptional, (9)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is NZ$1,109
includes taxes & fees
31 Dec - 1 Jan 2026
Award Winning Luxury Carriage House a short stroll from town!
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is NZ$368
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful & minutes from the Old Port with private parking
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is NZ$396
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is NZ$267
includes taxes & fees
1 Jan - 2 Jan 2026
In-town no frills 2 bedroom apt
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$452
includes taxes & fees
1 Jan - 2 Jan 2026
Brunswick Downtown Sugar Cube next to Bowdoin
9.8 out of 10, Exceptional, (171)
"Great location, very clean, everything we needed!"
United States
dawn m.
The price is NZ$480
includes taxes & fees
1 Jan - 2 Jan 2026
Glorious getaway on Portland's Eastern Promenade.
2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is NZ$684
includes taxes & fees
18 Jan - 19 Jan 2026
Chic 3-bedroom house in Munjoy Hill with off-street parking.
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is NZ$367
includes taxes & fees
30 Dec - 31 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland
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

Everything you need to know about Great Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Great Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Island holiday rentals we have selected for you start as low as NZ$231 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Great Island rentals

At Expedia, we put the best Great Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.