Great Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Great Island

On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Vacation Home in Bailey Island

10.0 out of 10, Exceptional, (233)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Exterior
Beautiful Oceanfront House- Stunning Water Views

Vacation Home in Harpswell

9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

Apartment in Harpswell

9.6 out of 10, Exceptional, (170)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Property grounds
Centerview cottage

Vacation Home in Harpswell

9.6 out of 10, Exceptional, (59)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
Centerview cottage
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (87)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$238 nightly
The price is $253
Nov 30 - Dec 1
Total with taxes and fees
The Weldon Hotel
Outdoor dining
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Vacation Home in Boothbay Harbor

10.0 out of 10, Exceptional, (20)
"We loved our stay in Boothbay. The cottage was clean and comfortable, location was ideal, easy walk into town and to the park. Everything was fantastic, would highly recommend. "
United States
Emma D.
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Property grounds
Captain's Guest Room w/private bath. Walk to everything.

Vacation Home in Bath

8.2 out of 10, Very Good, (21)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
Captain's Guest Room w/private bath. Walk to everything.
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Apartment in West Bayside

5.8 out of 10, (6)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
$144 nightly
The price is $145
Nov 24 - Nov 25
Total with taxes and fees
Studio Unit Walkable Everywhere
Interior
Spacious 4-bedroom house located in the heart of Portland, ME.

Vacation Home in Munjoy Hill

9.8 out of 10, Exceptional, (6)
"Clean, comfortable. "
United States
Nick P.
$743 nightly
The price is $810
Dec 24 - Dec 25
Total with taxes and fees
Spacious 4-bedroom house located in the heart of Portland, ME.
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland
TV
In-town no frills 2 bedroom apt

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
$154 nightly
The price is $156
Nov 24 - Nov 25
Total with taxes and fees
In-town no frills 2 bedroom apt
Exterior detail
Sunny Modern Oasis in Portland’s Trendy East End

Vacation Home in Munjoy Hill

10.0 out of 10, Exceptional, (62)
"Cozy, clean and quiet, within short walking distance to restaurants, coffee shops, breweries, distilleries and shopping. "
United States
Jane
Sunny Modern Oasis in Portland’s Trendy East End
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Cottage in Long Island

10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Vacation Home in South Bristol

9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
$436 nightly
The price is $475
Nov 24 - Nov 25
Total with taxes and fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Property grounds
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Vacation Home in Falmouth

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Interior
Oceanfront Cabin-Castle in Maine Woods

Vacation Home in Georgetown

9.8 out of 10, Exceptional, (43)
"Amazing property and location - just exactly what we were looking for - walking or driving to the beach every day - listening to the ocean and walking on the rocks and through the woods - truly magical. "
United States
Holly H.
Oceanfront Cabin-Castle in Maine Woods
Terrace/patio
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cabin in Boothbay

7.8 out of 10, Good, (7)
"Nice place to stay for a quick trip to the area! Would stay there again. "
United States
Lisa M.
$184 nightly
The price is $200
Dec 1 - Dec 2
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Walk to Breweries

Vacation Home in Munjoy Hill

10.0 out of 10, Exceptional, (92)
"Beautiful house in great area."
United States
Amber W.
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Vacation Home in East Deering

10.0 out of 10, Exceptional, (65)
"Nice stay. Good amenities. "
United States
Laura H.
$977 nightly
The price is $1,064
Dec 1 - Dec 2
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Outdoor dining
Knock on Wood | Airy Charm in Heart of Downtown

Apartment in Parkside

8.8 out of 10, Excellent, (25)
"Clean and comfortable in a great location. Walking distance to the Portland Farmer’s Market on Saturdays. Easy to access and very handy off street parking. Team was very easy to work with. "
United States
Natalie R.
$284 nightly
The price is $310
Nov 24 - Nov 25
Total with taxes and fees
Knock on Wood | Airy Charm in Heart of Downtown
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Island Hotel Reviews

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

10/10 Excellent
"Good clean stay "
joseph 3-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Portland

Find out more about Great Island

Everything you need to know about Great Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Great Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Island rentals

At Expedia, we put the best Great Island vacation 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 vacation.

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.

Explore a world of travel with Expedia