Search Vacation Homes in Chebeague Island

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Vacation Homes in Chebeague Island

Captain's Guest Room w/private bath. Walk to everything.

Bath
8.2 out of 10, Very Good, (21)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
United States
Benjamin E.
$104 nightly
The price is $113
Nov 18 - Nov 19
Total with taxes and fees
Captain's Guest Room w/private bath. Walk to everything.

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.
$151 nightly
The price is $164
Nov 18 - Nov 19
Total with taxes and fees
The Outlet Studio, Rustic Comfort w Fireplace

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.
$409 nightly
The price is $414
Dec 2 - Dec 3
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!

Mid Coast Getaway w/ water views

West Point
9.2 out of 10, Wonderful, (5)
"You couldn’t ask for a better view, it was everything we had hoped and more."
United States
Andrew S.
$192 nightly
The price is $202
Nov 20 - Nov 21
Total with taxes and fees
Mid Coast Getaway w/ water views

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay the weekend after Christmas. The home had absolutely everything we needed and was both comfortable and beautiful! Everything was clearly labeled and so easy settle in. Very close to the beach which was awesome to visit even in the winter!"
United States
Elizabeth M.
$443 nightly
The price is $483
Nov 18 - Nov 19
Total with taxes and fees
Beach House ∆ Prime Location ∆ Steps to the Ocean

Captain's 1BR Quaters. Quiet. Walk to everything. No fees. Dogs stay free!

Bath
7.6 out of 10, Good, (12)
"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!"
United States
Carol N.
$92 nightly
The price is $100
Dec 1 - Dec 2
Total with taxes and fees
Captain's 1BR Quaters. Quiet. Walk to everything. No fees. Dogs stay free!

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

Brunswick
9.2 out of 10, Wonderful, (5)
"Had a great stay here, the property was clean and came as advertised"
United States
Trevor S.
$322 nightly
The price is $351
Nov 18 - Nov 19
Total with taxes and fees
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Serenity between the lakes and seashore

Westbrook
9.8 out of 10, Exceptional, (24)
"Good location near lots of hiking and not far from Portland "
United States
Laura P.
$288 nightly
The price is $314
Nov 29 - Nov 30
Total with taxes and fees
Serenity between the lakes and seashore

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.
$255 nightly
The price is $269
Nov 30 - Dec 1
Total with taxes and fees
Fantastic Waterfront Views

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

Brunswick
8.8 out of 10, Excellent, (23)
"It was the perfect location and easy to get to. The best beds ever and clean open environment was so welcoming. Thank you. Will stay again "
United States
Olga T.
$367 nightly
The price is $400
Nov 18 - Nov 19
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Huge Historic Downtown Townhome

West End
9.8 out of 10, Exceptional, (8)
"Wonderful accommodations"
United States
Sean
$368 nightly
The price is $401
Nov 18 - Nov 19
Total with taxes and fees
Huge Historic Downtown Townhome

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

Munjoy Hill
10.0 out of 10, Exceptional, (35)
"Adorable and pristine place, with many thoughtful amenities. Great location. Incredible host. Loved our stay."
United States
Brant H.
$303 nightly
The price is $330
Nov 18 - Nov 19
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!

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.
$402 nightly
The price is $438
Nov 18 - Nov 19
Total with taxes and fees
Plush 5BR OOB Haven w/ Fire Pit

Spacious 5BR Family Dream with Private Beach Access

Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
United States
rebecca c.
$463 nightly
The price is $505
Nov 18 - Nov 19
Total with taxes and fees
Spacious 5BR Family Dream with Private Beach Access

Orchid Harbor, Bailey Island 3BR

Harpswell
9.8 out of 10, Exceptional, (7)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
United States
Jason M.
$411 nightly
The price is $415
Nov 24 - Nov 25
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR

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.
$435 nightly
The price is $475
Nov 18 - Nov 19
Total with taxes and fees
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Generous Living in a Warm, Welcoming Home

Topsham
$488 nightly
The price is $532
Dec 10 - Dec 11
Total with taxes and fees
Generous Living in a Warm, Welcoming Home

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

Freeport
9.6 out of 10, Exceptional, (15)
"The place was clean and comfortable as advertised, with plenty of bedroom space and a large dining area where we ate and did work. Easy to drive to Portland and other attractions in the area! The neighborhood itself is just a quiet residential area. Worked well for our little winter weekend!"
United States
Olivia U.
$436 nightly
The price is $456
Nov 18 - Nov 19
Total with taxes and fees
Spacious Country Home Freeport, Only 5 min to LL Bean!

Modern Getaway by the Sea

Cash Corner
10.0 out of 10, Exceptional, (2)
"Very comfortable home. Host was easily available for questions. House was extremely clean and well located in South Portland. Host lives on bottom floor in property but we did not run into him. Highly recommend this property. "
United States
Susan R.
$389 nightly
The price is $413
Nov 18 - Nov 19
Total with taxes and fees
Modern Getaway by the Sea

OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA

Old Orchard Beach
10.0 out of 10, Exceptional, (5)
"My family had a fantastic stay at this house. Although the property had no ratings since we were the first renters, I was hopeful about our experience and was not disappointed. We had seven adults and a 14-month-old stay for three nights. Jason was extremely responsive to all of our questions before our arrival and during our stay. There was no portable crib or high chair when we arrived, and when I contacted Jason, he had them delivered within the hour! There was plenty of space in the living...
United States
Mary W.
$476 nightly
The price is $519
Nov 18 - Nov 19
Total with taxes and fees
OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
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

Find out more about Chebeague Island

Chebeague Island Vacation Homes information

Number of reviews
253
Accommodation
623 Vacation Homes
Lowest Price
$100
Highest Price
$532

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