Holiday Homes in Chebeague Island

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Chebeague Island and around

Escape to Positive Outlook
Dining

Escape to Positive Outlook

The price is €419
includes taxes & fees
29 Aug - 30 Aug
Escape to Positive Outlook
Mid Coast Getaway w/ water views
TV

Mid Coast Getaway w/ water views

9.0 out of 10, Wonderful, (2)
"You couldn’t ask for a better view, it was everything we had hoped and more."
Mid Coast Getaway w/ water views
Phenomenal Home on Coast of Maine
Dining

Phenomenal Home on Coast of Maine

8.8 out of 10, Excellent, (42)
"Had a great stay. Killer views!!"
The price is €501
includes taxes & fees
9 Sept - 10 Sept
Phenomenal Home on Coast of Maine
Fantastic Waterfront Views
3 bedrooms, WiFi

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is €498
includes taxes & fees
17 Aug - 18 Aug
Fantastic Waterfront Views
Award Winning Luxury Carriage House a short stroll from town!
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
Award Winning Luxury Carriage House a short stroll from town!
Captain's Quarters 1BR Apartment. Walk to everything.
Property grounds

Captain's Quarters 1BR Apartment. Walk to everything.

7.8 out of 10, Good, (7)
"Very nice cozy place to make home base for a week. Had everything I needed and owner was very responsive with all of my questions. Primary destination was Bath and very convenient to everything I needed. Thank you!"
Captain's Quarters 1BR Apartment. Walk to everything.
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Property grounds

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.4 out of 10, Good, (12)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is €144
includes taxes & fees
17 Aug - 18 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Captain's Quarters 2BR Apartment. Walk to Everything!
Property grounds

Captain's Quarters 2BR Apartment. Walk to Everything!

8.8 out of 10, Excellent, (6)
The price is €218
includes taxes & fees
17 Aug - 18 Aug
Captain's Quarters 2BR Apartment. Walk to Everything!
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is €251
includes taxes & fees
15 Sept - 16 Sept
Camp Forever cottage
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (32)
"Very clean and comfortable. Great care has gone into making it feel like a home well loved."
The price is €319
includes taxes & fees
19 Aug - 20 Aug
Full sized home
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Fridge, microwave, oven, stovetop

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at this peaceful oceanside property in Harpswell, Maine. The setup—with a main house, attached apartment, and a charming bunkhouse—was perfect for our two families and adult children. There was plenty of space for everyone to relax and unwind.The backyard is absolutely stunning, filled with beautiful flowers and lush grass, and it opens up to a tranquil ocean inlet. We especially loved the hammock spot, perfect for a good book or an afternoon nap, and the back porch...
The price is €1,343
includes taxes & fees
25 Aug - 26 Aug
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Classic New England Waterfront
Private kitchen

Classic New England Waterfront

The price is €987
includes taxes & fees
1 Sept - 2 Sept
Classic New England Waterfront
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Private kitchen

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is €535
includes taxes & fees
16 Aug - 17 Aug
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (20)
"Nice place, I'd stay again!"
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (5)
"Had a great stay here, the property was clean and came as advertised"
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Exterior

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (20)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
The price is €922
includes taxes & fees
2 Sept - 3 Sept
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Waterfront, Luxury, Spacious home in Freeport!
Terrace/patio

Waterfront, Luxury, Spacious home in Freeport!

10.0 out of 10, Exceptional, (27)
"Great location - close to downtown Freeport. Beautiful property with plenty of comfortable sleeping options"
The price is €1,404
includes taxes & fees
1 Sept - 2 Sept
Waterfront, Luxury, Spacious home in Freeport!
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
The price is €513
includes taxes & fees
26 Aug - 27 Aug
30 Acres with Woodland Trails and Playground
Luxury King Room with Parlor and Balcony
Property grounds

Luxury King Room with Parlor and Balcony

The price is €619
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony
Spacious Country Home Freeport, Only 5 min to LL Bean!
Interior

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.6 out of 10, Exceptional, (15)
"We had a great time here. It was great."
The price is €555
includes taxes & fees
19 Aug - 20 Aug
Spacious Country Home Freeport, Only 5 min to LL Bean!
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 Chebeague Island Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"I opted for the economy of the shared bath. It saved me a lot of money. I can't offer an opinion about the rooms with private baths. My room was very good. I will stay here again."
James 1-night trip
Posted 23 hours ago
Inn at St John Portland In-Town