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Vacation Homes in Chebeague Island

Captain's 2BR Quarters. Walk to everything . No fees. Dogs Free'

Bath
8.6 out of 10, Excellent, (10)
"Great location and interesting layout in this historic house. It was the perfect respite for our stay before our puffin tour the next day and close to town for a concert on the common and restaurants. Note : to access one of the bedrooms you need to go through the bathroom, but it worked out fine. Dmitri was super communicative and was kind enough to let us know we left a pair of shoes there after we departed. Since we were still in the area, he left them on the porch for us to retrieve, which...
United States
Erika B.
The price is AED 478
AED 601 total
includes taxes & fees
26 Nov - 27 Nov
Captain's 2BR Quarters. Walk to everything . No fees. Dogs Free'

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 AED 480
AED 1,387 total
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!

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 price is AED 314
AED 603 total
includes taxes & fees
16 Nov - 17 Nov
The Outlet Studio, Rustic Comfort w Fireplace

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.
The price is AED 294
AED 400 total
includes taxes & fees
1 Dec - 2 Dec
Captain's 1BR Quaters. Quiet. Walk to everything. No fees. Dogs stay free!

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.
The price is AED 521
AED 1,773 total
includes taxes & fees
16 Nov - 17 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean

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.
The price is AED 360
AED 1,141 total
includes taxes & fees
29 Nov - 30 Nov
Serenity between the lakes and seashore

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (13)
"The place is amazing with lots of room for a family, and great views of the water from almost everywhere. The neighborhood is quiet and the people were very friendly. "
United States
Joseph V.
The price is AED 463
AED 988 total
includes taxes & fees
30 Nov - 1 Dec
Fantastic Waterfront Views

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.
The price is AED 347
AED 742 total
includes taxes & fees
17 Nov - 18 Nov
Mid Coast Getaway w/ water views

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 AED 496
AED 1,289 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Centerview cottage

Harpswell
9.6 out of 10, Exceptional, (59)
"We loved the view! The hosts were very quick to respond to any questions. This is a lovely spot to relax and watch the sea."
United States
Anonymous traveler
The price is AED 779
AED 1,381 total
includes taxes & fees
1 Dec - 2 Dec
Centerview cottage

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.
The price is AED 648
AED 1,927 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 5BR Family Dream with Private Beach Access

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

Brunswick
8.8 out of 10, Excellent, (23)
"Great location for baileys island and popham"
United States
Anonymous traveler
The price is AED 551
AED 1,469 total
includes taxes & fees
16 Dec - 17 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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 AED 524
AED 1,777 total
includes taxes & fees
16 Nov - 17 Nov
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

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 AED 482
AED 1,618 total
includes taxes & fees
17 Nov - 18 Nov
Plush 5BR OOB Haven w/ Fire Pit

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.
The price is AED 601
AED 1,523 total
includes taxes & fees
26 Nov - 27 Nov
Orchid Harbor, Bailey Island 3BR

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (57)
"Nice, quiet location. Bed is super comfortable, and everything is neat and clean inside. We were a little confused which kayaks we could use and how to get them down to the water, and we were encouraged to use life vests, but there were none available (and we did not bring any with us). Otherwise, hosts were very responsive and we had a nice time."
United States
Lisa K.
The price is AED 845
AED 1,421 total
includes taxes & fees
30 Nov - 1 Dec
Camp Forever cottage

The Sea Gaze - 5BR with Beach Path

Old Orchard Beach
10.0 out of 10, Exceptional, (1)
"Beautiful house and great location "
United States
Nicole K.
The Sea Gaze - 5BR with Beach Path

The Barnhouse with hot tub

New Gloucester
9.8 out of 10, Exceptional, (6)
"Clean, quiet, and comfortable respite from the bustle of the city. The property is well-stocked and welcoming. We had our own private outdoors area with a nice hot tub and seating area. Our family enjoyed our time at The Barnhouse. It was within driving distance to our various activities near the Portland coastal region."
United States
Lisa K.
The price is AED 547
AED 1,125 total
includes taxes & fees
16 Nov - 17 Nov
The Barnhouse with hot tub

Modern Cottage with Peeks of Ocean Views

Cape Elizabeth
10.0 out of 10, Exceptional, (1)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is AED 1,047
AED 1,622 total
includes taxes & fees
14 Dec - 15 Dec
Modern Cottage with Peeks of Ocean Views

Generous Living in a Warm, Welcoming Home

Topsham
The price is AED 692
AED 1,979 total
includes taxes & fees
10 Dec - 11 Dec
Generous Living in a Warm, Welcoming Home
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