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Vacation rentals in Chebeague Island

Vacation rentals in Chebeague Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chebeague Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Weather's Edge, Freeport
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Weather's Edge, Freeport

    Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

    What guests are saying:

    “I loved my stay at Sandy and Jerry’s. This was my first time using air bnb and it was a great experience. I am used to staying at hotels and this was better! They provided so many nice touches, like coffee creamer and breakfast bars, that made it extra convenient. I was on a solo get away so I really appreciate how their setup allows 100% privacy. I did not hear them once! The location is great - a very quite and seemingly safe neighborhood with people out walking and enjoying their day. Sandy and Jerry offered to let me check-in early to avoid driving in a snow storm and also shoveled out my entrance walkway and put salt to melt the ice. Very thoughtful and kind. Very comfortable bed and awesome pillows. 10/10 and will be staying again!”

  • Kelley's Ocean Veiw Cottage
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bathroom
    Kelley's Ocean Veiw Cottage

    Rustic cottage that's been in my family since 1893. Ocean view on a mile around Island With Beach Access, Open field for all sorts of games etc. a great island for small walks, very friendly neighbors with spectacular night views of Portland and the stars with no light pollution. 20 min to Freeport for shopping and 20 min. to Portland for Night life,Dinning, Work.Etc.

    What guests are saying:

    “This cottage was the perfect end of summer getaway for our family of 4. There was plenty of room for myself and my husband, our 9 year old, and 2 year old. The beds were unbelievably comfortable, and the views out the windows could not have been more beautiful. This is not a 5 star luxury accommodation, but if you need a sparkling clean and comfortable place to relax with your family, this is absolutely it. 3 bedrooms so everyone has space, a large living room with comfortable furniture, a big TV and super fast wifi made it easy to relax and watch a movie at night. As noted in the listing, the bathroom is very small, but we made it work and it didn't take anything away from the experience. There is a full sized washer and dryer in the house, so you don't have to take sandy seawater clothes back home with you...a real perk when traveling with kids! The kitchen was well stocked with everything we needed, and the wraparound deck had lots of seating options for morning coffee, card games during the little ones nap, and watching the kids run around the huge yard. The nature preserve on the island was a beautiful way to spend a morning. (Of note, if you are traveling with little ones, the nature preserve is not very stroller friendly, but that certainly doesn't have anything to do with the house.) The location was perfect for a day trip to freeport and old orchard beach, and one to portland. It was very hard to say goodbye to the area to head back home, but we look forward to returning!”

  • Island Cottage Getaway in Casco Bay!!
    SUPERHOSTIsland · 6 guests · 8 beds · 1 bathroom
    Island Cottage Getaway in Casco Bay!!

    Log cabin includes a master bedroom, loft w/5 beds & a small room with bunkbeds. It has solar power, a bathroom/hot shower, kitchen, dining room, den, living room, & a big private yard. It's close to the Portland airport, close to 5 star restaurants, and is on the outskirts of a beautiful harbor. There are only a few other cabins and no roads on the island. Island fun such as fishing, swimming, camping, paddle boarding, kayaking, and exploring will keep you busy for your stay.

    What guests are saying:

    “I hestitate to write a great review because I don't want everyone to know about this place! It is really a one-of-kind experience. From the boat ride over, to the lobster delivery, to the spectacular beach combing. The island breezes are so amazing. Our two small boys loved the trampoline, gathering wood from the forest out back, going to the beach and exploring the tidepools, finding seaglass, searching for crabs under the rockweed, and watching the boats go by. There was a family of ducks at the cove there and we loved seeing them every day. I would recommend renting a boat if you are going to be there for a full week, you can run out of things to do on a small island unless you bring your own fun. So many nearby islands with places to explore, next time we come we would definitely rent a boat. Also, the coffee pot is a french press and is a bit old, so if you are picky about your coffee you may want to bring your own set up! The fridge is a propane one and super duper cold, the produce didn't fare well so bring a cooler to keep tender items in. Bed was super duper comfy, much better than we expected in such a rustic experience! I think this place is perfect for our family of four, but much more than that would be tricky with only one sink shared between kitchen and bathroom. But you can't beat it's location! Thank you so much Jerry and Marie!”

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Popular amenities for Chebeague Island holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chebeague Island

Classic Maine Oceanfront Cottage
SUPERHOSTEntire cottage
Classic Maine Oceanfront Cottage
Price:€168 / night
Chebeague Island, ME Garden View Room for 1
SUPERHOSTPrivate room
Chebeague Island, ME Garden View Room for 1
Price:€66 / night
Waterfront Cottage On Basin Cove - Amazing Sunsets
SUPERHOSTEntire house
Waterfront Cottage On Basin Cove - Amazing Sunsets
Price:€198 / night
Unique Setting on the Point
SUPERHOSTPrivate room
Unique Setting on the Point
Price:€79 / night
Long Island Beach Cottage: The Lobster Trap
SUPERHOSTEntire cottage
Long Island Beach Cottage: The Lobster Trap
Price:€86 / night
Beachside Cottage-5 min to Portland (Queen)
SUPERHOSTPrivate room
Beachside Cottage-5 min to Portland (Queen)
Price:€31 / night
Stylish Room Near Old Port, Beaches, Dirigo Room
SUPERHOSTEntire flat
Stylish Room Near Old Port, Beaches, Dirigo Room
Price:€79 / night
Suite at a convenient location.
SUPERHOSTPrivate room
Suite at a convenient location.
Price:€84 / night
Amazing views! Oceanfront with private entrance
SUPERHOSTPrivate room
Amazing views! Oceanfront with private entrance
Price:€132 / night
Sweet Retreat
SUPERHOSTEntire bungalow
Sweet Retreat
Price:€79 / night
Apartment remodel for your enjoyment and comfort.
SUPERHOSTEntire flat
Apartment remodel for your enjoyment and comfort.
Price:€159 / night
Cumberland Maine, near Portland/Freeport luxury
SUPERHOSTEntire house
Cumberland Maine, near Portland/Freeport luxury
Price:€176 / night
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