Search Vacation Homes in Chebeague Island

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in Chebeague Island

Dining
Escape to Positive Outlook

Escape to Positive Outlook

West Point
10.0 out of 10, Exceptional, (2)
"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 SAR 355
SAR 758 total
includes taxes & fees
4 Dec - 5 Dec
Escape to Positive Outlook
Interior
Captain's Quarters Getaway. Peace& quiet. Walk to everything. No fees.Pets free!

Captain's Quarters Getaway. Peace& quiet. Walk to everything. No fees.Pets free!

Bath
7.6 out of 10, Good, (12)
"Quaint and historic old house in a quiet neighborhood. The location was very convenient to the sights around Bath."
United States
Ricky R.
Captain's Quarters Getaway. Peace& quiet. Walk to everything. No fees.Pets free!
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable and homey Great location to the outlets. "
United States
Patricia C.
The Outlet Studio, Rustic Comfort w Fireplace
TV
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 SAR 511
SAR 1,450 total
includes taxes & fees
3 Dec - 4 Dec
Mere Point Sunrise Views at Eastern Shore!
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (14)
"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. "
United States
Heather S.
The price is SAR 473
SAR 1,018 total
includes taxes & fees
3 Dec - 4 Dec
Fantastic Waterfront Views
Property grounds
Captain's Quarters 2BR Getaway. Walk to everything. No fees. Pets welcome.

Captain's Quarters 2BR Getaway. Walk to everything. No fees. Pets welcome.

Bath
8.6 out of 10, Excellent, (10)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
United States
A M.
Captain's Quarters 2BR Getaway. Walk to everything. No fees. Pets welcome.
Beach nearby, sun loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"It was clean and neat and just steps to the beach. It had everything you could possibly need."
United States
Mare E.
The price is SAR 532
SAR 1,811 total
includes taxes & fees
3 Dec - 4 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean
Fridge, microwave, oven, stovetop
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 SAR 507
SAR 1,325 total
includes taxes & fees
3 Dec - 4 Dec
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Fridge, microwave, oven, stovetop
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, (23)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is SAR 563
SAR 1,514 total
includes taxes & fees
3 Dec - 4 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Outdoor dining
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 SAR 788
SAR 1,362 total
includes taxes & fees
31 Dec - 1 January 2026
Camp Forever cottage
Interior
Plush 5BR OOB Haven w/ Fire Pit

Plush 5BR OOB Haven w/ Fire Pit

Old Orchard Beach
10.0 out of 10, Exceptional, (2)
"We stayed for 3 nights and I can honestly say it was the cleanest place I ever stayed in Old Orchard Beach. The neighborhood was really quiet, so it was awesome for our little ones to go to sleep early. They had everything you could ever need for a trip, and more. The only complaint we have is the sink nasal spraying everywhere, which seemed to only be a water pressure issue, so no big deal at all. The host was very communicative for our upcoming trip. All things considered, we definitely will...
United States
Alex B.
The price is SAR 662
SAR 1,855 total
includes taxes & fees
3 Dec - 4 Dec
Plush 5BR OOB Haven w/ Fire Pit
Private kitchen
Spacious Portland Home + Parking

Spacious Portland Home + Parking

Parkside
9.0 out of 10, Wonderful, (2)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is SAR 619
SAR 2,176 total
includes taxes & fees
30 Dec - 31 Dec
Spacious Portland Home + Parking
Terrace/patio
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 SAR 702
SAR 1,383 total
includes taxes & fees
7 Dec - 8 Dec
Modern & Sunny House Steps from the Promenade. Private Parking!
Paper towels
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 SAR 619
SAR 1,698 total
includes taxes & fees
3 Dec - 4 Dec
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Fridge, microwave, oven, stovetop
Huge Historic Downtown Townhome

Huge Historic Downtown Townhome

West End
9.8 out of 10, Exceptional, (8)
"We gathered as a family to spend one night in Portland and we could not have been happier with the location. "
United States
Stephen M.
The price is SAR 502
SAR 1,517 total
includes taxes & fees
3 Dec - 4 Dec
Huge Historic Downtown Townhome
1 bedroom, internet, bed sheets
Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood

Back Cove
The price is SAR 525
SAR 859 total
includes taxes & fees
3 Dec - 4 Dec
Charming 1-bedroom ADU in wonderful Portland neighborhood
Property grounds
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 SAR 560
SAR 1,170 total
includes taxes & fees
3 Dec - 4 Dec
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Microwave, oven, stovetop, dishwasher
The Barnhouse with hot tub

The Barnhouse with hot tub

New Gloucester
9.8 out of 10, Exceptional, (6)
"Thank you Bethany for a most wonderful stay. What a beautiful property you have here. We really loved the opportunity to enjoy the barn house. Hope you and your family have an awesome summer. "
United States
Jeffrey R.
The price is SAR 709
SAR 1,345 total
includes taxes & fees
15 Dec - 16 Dec
The Barnhouse with hot tub
Private kitchen
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 SAR 938
SAR 2,643 total
includes taxes & fees
3 Dec - 4 Dec
Classic New England Waterfront
Living area
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach
9.4 out of 10, Exceptional, (14)
"The property was in a good location from everything available in the beach area and the house had enough space to accommodate all 12 of us."
United States
Wayne R.
The price is SAR 623
SAR 1,935 total
includes taxes & fees
9 Dec - 10 Dec
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Easy check in, cozy and clean 👍"
Kathryn 2-night trip
Posted 1 day ago
Fireside Inn & Suites Portland