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Chebeague Island: Houses, Cottages & More (729)

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Additional fees apply. Taxes may be added.
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                                                                                                    Recent Chebeague Island Reviews

                                                                                                    Wonderful, peaceful time in a historical building in Diamond Cove.

                                                                                                    5 of 5
                                                                                                    We had a lovely stay on Great Diamond Island. A magical place just a short ferry ride from Portland. Ellen and John were perfect hosts - they greeted us from our ferry and took time to show us their property & were available for any questions throughout our stay. The house was perfect for our family. Very clean and well equipped - along with toys for our children and bikes for us to explore. We enjoyed exploring the island, using the swimming pool, playing in the games room (fantastic old ten pin bowling!) It was a treat to wake up to bird song and the island is very safe due to no (or little amount) of vehicles. We enjoyed dinner at the inn, coffee and ice cream from the general store. It's a very chilled and quiet island so not recommended for those looking for action - but perfect for a couple or small family looking to escape and get away from it all. We hope to return again next summer and highly recommend this lovely house on a beautiful and peaceful island. Thank you Ellen and John!
                                                                                                    • Submitted: Aug 15, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Even better than expected!

                                                                                                    5 of 5
                                                                                                    Underoaks is the perfect setting to relax and unwind. The waterviews from the house are spectacular! The kids really enjoyed climbing on the rocks at the beach. The house is spacious, and even with 11 of us, there was plenty of room to all be together or to have private time. Portland and Freeport are only a shirt drive away if interested in shopping or going out to eat. Jenny was great about getting in touch through email or phone and offered great suggestions for things to do. We will definitely be looking into reserving the house again in the future!
                                                                                                    • Submitted: Aug 14, 2016
                                                                                                    • Stayed: Jul 2016

                                                                                                    A clean, comfy & very homey abode in a wonderful neighborhood.

                                                                                                    5 of 5
                                                                                                    From the outset both Monique & Matt were very gracious & open. The home is very well appointed & furnished including 2 gorgeous outdoor seating areas. The first floor plan is nice & open, and the bedrooms on the second floor offer lots of privacy. Falmouth is close enough to Portland (in Old Port in 20 minutes, 25 with "traffic" lol), and even places like Boothbay Harbor are only an hour away via car - which makes for some nice day trips. The fenced backyard was a great little playground for Ruby (our welsh springer) and she enjoyed the nice strolls down to the water's edge. I recommend you bring a couple box fans to pull in the wonderful Maine fresh air. There are nice circulating fans located throughout the house so you just need a way to draw in the outdoor air.
                                                                                                    • Submitted: Aug 13, 2016
                                                                                                    • Stayed: Aug 2016