Refurbished Brick, Waterfront Home on Cushing's Island.
House in Cushing Island, ME
10 guests · 6 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Includes essentialsGarden, Pets allowed, Kitchen or Kitchenette and more
About this house rental
'The Jail' on Cushing's Island - a WWII, refurbished military jailhouse located on the eastern side of Cushing's Island, in Casco Bay. The large brick house enjoys sweeping views of Spring Cove, the island dock, and Whitehead Passage. The house is incredibly well-equipped and can easily accomodate larger groups. There are 5 bedrooms, 3 small jail cells with single beds (perfect/fun for the kids!), a bunkhouse and 4 full baths. The house rental rate allows up to 10 guests, but will consider additional guests for an additional charge.
Cushing's Island is a privately-owned island in Casco Bay where roughly 45 families live seasonally. It is one of Maine's most beautiful islands with extensive walking trails that access it's stunning landscape. Walking, birding, swimming, sunbathing, tennis, fishing, kayaking, collecting sea glass, picking berries, exploring, or just relaxing on the porch are how most people fill their days. A year-round caretaker drives the only vehicle on the island. There are no shops, restaurants or stores on Cushing's. Ferry service leaves from Portland Harbor and runs from Memorial Day to Labor Day. Cushing's Island provides the perfect setting for a quiet, secluded family vacation only minutes from downtown Portland (where, if desired, one can find great restaurants, shopping, and museums).
Keywords: Large Island home, waterfront, brick, ocean view
Cushing's Island is a privately-owned island in Casco Bay where roughly 45 families live seasonally. It is one of Maine's most beautiful islands with extensive walking trails that access it's stunning landscape. Walking, birding, swimming, sunbathing, tennis, fishing, kayaking, collecting sea glass, picking berries, exploring, or just relaxing on the porch are how most people fill their days. A year-round caretaker drives the only vehicle on the island. There are no shops, restaurants or stores on Cushing's. Ferry service leaves from Portland Harbor and runs from Memorial Day to Labor Day. Cushing's Island provides the perfect setting for a quiet, secluded family vacation only minutes from downtown Portland (where, if desired, one can find great restaurants, shopping, and museums).
Keywords: Large Island home, waterfront, brick, ocean view
Amenities
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Laundry
Balcony or Patio
Dishwasher
Garden
Family friendly
Map of Cushing Island, ME
$$$$
Ratings and reviews
5.0 / 5.0
Love it!
Wonderful stay, beautiful island, incredibly thoughtful hosts!
5.0 / 5.0
One of a kind property
Really fabulous stay at the jail - the island is unique and beautiful, with a lot to do (fort/beaches/piers/tennis courts/nature preserve), everyone on the island was extremely friendly, and our whole party had a wonderful time. Portland is just 15m away by ferry or sea taxi, yet the island is its own little quiet wonderful world
5.0 / 5.0
Peaceful Adventuring
Cushing’s Island has something for everyone. If you like adventure you can discover hidden trails that may lead to spectacular views of rocky cliffs on the blue Atlantic, climb rocks on the coast, and kayak the bay. If you want to relax you can look for sea glass on the shore (lots to be found!), fish, sit on the sandy beach, watch the sunrise or sunset from the beach or dock or read a book at the spacious jailhouse. We had planned to visit Peak’s Island for a day but we did not want to leave this island we quickly grew to love.
We had 8 family members and our dog... hadplenty of room for everyone. The kitchen was very nice and well equipped. The second floor suite provided a spacious sanctuary. The porch is enormous and there were two additional decks for spending time outside. The house was not air conditioned but with cool New England air, it was not needed. We did not use the bunk house but it offered a cute loft bedroom and living room for a nice stay. Internet met needs of the youth!
We were welcomed warmly on arrival and everyone we met was friendly. Though we went most places without seeing anyone or very few people. Many times we felt we had the island all to ourselves. Will return!!
5.0 / 5.0
Love it.
Magical island, spacious and well-equipped home, and wonderful hosts. Could not have been better.
5.0 / 5.0
Perfect getaway
What a magical island! We all had such a good time walking and kayaking and lounging every day.
5.0 / 5.0
Another great family vacation!
This was our sixth year at Cushings and we love it more each time. The jail is a one-of-a-kind accommodation and is stocked with everything you would ever need. We added a new jigsaw puzzle and a corkscrew this year. Enjoy lazy days punctuated with beautiful sunsets. Search for sea glass. Go shopping in town. Do nothing or stay busy; it’s your choice. The only bad day is the one when you have to leave.
5.0 / 5.0
Wonderful Week!
Fourteen of us stayed here for a wonderful week! The island provided so much to do, the trails, the water, the kyaks, the raspberries, the sea glass, the sunrises and sunsets, the views, the friendly people, the flowers! The house was very well stocked, the architectural design and detail beautiful. The history of the island is very interesting, so many people took the time to share details with us. We had 3 families, with 8 children ranging in age from 9 to 15. The kids explored, added sculptures to Spicer's Cove, divided into teams to see who could find all three gazebos first, collected sea glass, kayaked for ice cream to Peaks, played croquet, jumped off the dock, and just enjoyed the freedom the island provided. Matt was ever so patient with our many questions and so easy to work with. A definite repeat trip in our future! I would suggest if you are a large group like ours, and plan to go into Portland or surrounding areas, look into a water taxi, it's a bit more economical and flexible, and will pick you up at the dock, which provides the lovely view from The Jail's porch!
5.0 / 5.0
A Week We'll Never Forget!
Our group of 13 (3 families) spent an amazing week at The Jail this summer. We enjoyed our meals on the deck while overlooking Spring Cove. We never felt the need to leave the island. The house was spacious and well stocked and island was so beautiful. We found a new trail to walk on every day. We all took turns on the kayaks and even went to Peaks Island several times to stock up on a couple grocery staples so we didn't have to back to the mainland. A very special, unforgettable place to visit!
5.0 / 5.0
Perfect Vacation Rental
This was my second stay in this absolutely ideal vacation rental, and I plan to return every year. Anyone who considers staying here should know that they are actually getting two amazing benefits -- the house AND the island. Cushings Island is one of the best kept secrets in Maine; take a twenty minute ferry from downtown Portland and you enter a quiet, magical world that feels like a step back in time. You are instantly struck by how peaceful and calm the island feels: Empty beaches, dock-jumping, raspberry picking, quiet bucolic walks in the woods, ivy-covered abandoned forts. Even on rainy or foggy days, it's still wonderful to explore the island. Then, of course, there's the house -- which is a perfect choice for families or a combined rental with friends. It has everything you could want -- the kitchen is extremely well furnished with two dishwashers and two ovens (a big benefit when the house is full) and all the pans or appliances you need. We have made some truly amazing meals in this kitchen. Something else we really appreciated, because we stayed as two families with lots of kids, is how quiet the house is -- we can be as loud as we want in the dining room at night, without bothering the kids who are tucked away in their "jail cells" sleeping. The decor is a wonderful blend of historical preservation (high-ceilings, thick oak doors, and the ridiculously charming jail-cell elements) and new updates (refinished floors, television, stereo). The owners have clearly gone to great lengths to make sure that their renters are happy. I would unreservedly recommend this house to anyone who wants to anyone who wants to have an amazing, memorable, and relaxing summer vacation.
5.0 / 5.0
Wonderful Family Get-away
My family recently stayed at the Jail for the last two weeks of August and had a fabulous time! The kitchen is fully stocked with everything you need, so we made some fabulous meals. The kids loved sleeping in the jail cells, but proceeded to check out every other bed in the place too... We went on daily hikes, the kids loved dock jumping, exploring the forts, fishing off the pier, flying kites and searching for seaglass. I was truely sorry to come home but hope to get back some time soon...
5.0 / 5.0
Amazing Island Getaway!
Our family had an unbelievable experience at the Jail this summer. The property is gorgeous (the pics really don't do it justice!) and the owners have gone above and beyond to make the house welcoming and fun. The kitchen is STOCKED with every utensil/pan a cook could want and spacious enough for several people to be preparing food at once. All the bedrooms were airy and clean and so inviting. The outside has decks on every side of the building and lots of room to dine and entertain. There are books and games for the eventual rainy day (we never had one!).
Cushing itself was magical with sandy beaches, lots of beautiful hiking trails circling the island, dock jumping, berries to pick, tennis courts, and an island swimming pool. We also paddled to Peaks Island with the house kayaks for ice cream and convenience store runs which was fantastic.
Our 2 sons aged 7 and 10 had an absolute blast. Thank you Danas! We will be back!
5.0 / 5.0
Peaceful Adventurous Family Vacation
The house offered my family and I one of the best vacations we've had yet. The house was big enough for the 9 of us (and the dogs) to never feel cramped. The kitchen offered plenty of room for as many as 5 to be cooking or prepping meals at the same time. My folks took the spectacular and spacious master suite upstairs which offered them a place of solitude on rainy days while the kids took over the living room downstairs.
We had most of our dinners out on the deck, and spent many hours reading there as well. Daily walks, runs, tennis was had by all while we stayed on this incredible secluded island. We wanted an escape from populated places and the house and Cushings offered exactly that. If we saw 2 dozen people during our stay I'd be surprised. Those we did meet had stories and history of the island to tell.
The House was incredible. The island was great (we even kayaked twice to Peaks), The experience was wonderful. My correspondence with the home owners was always pleasant and they were very informative, helpful and courteous.
5.0 / 5.0
Magical island, incredible vacation home
We stayed in this home the last week in June and it was one of the best vacation experiences we've ever had. The house accommodated two families (9 people total) beautifully, with extra bedrooms to spare! The three boys (ages 8,10, and 10) absolutely loved sleeping in the individual jail cells, while the girls had their pick of three other bedrooms in the jail area. The adults each had their own suite with private bathrooms - the upstairs suite is like its own apartment and the front corner bedroom/bath is charming and comfortable.
The kitchen is incredible! Two ovens, two dishwashers, counter space galore, and way more well-stocked with utensils and gadgets than my kitchen at home. The entire house is similarly well-accommodated with plenty of sheets, towels, blankets, hundreds of books, games, etc.
Cushing's Island is such a special place. The kids especially enjoyed the freedom of exploring this magical island - no cars, no stores, just beaches and trails and old military forts. Everyone we encountered was friendly and helpful. If you are a jogger, the 3-mile loop around the perimeter of the island might very well be the most beautiful run you ever experience.
We loved our stay at "The Jail" and hope to make it an annual tradition!
5.0 / 5.0
The Best Family Vacation Ever
I searched for a place for my family for a couple of months and came across the Jail. I highly recommend this for anyone who loves nature and the quiet life. Although we kept ourselves busy every minute with walks around the island, climbing the rocks and cliffs, and searching for beach glass, and just relaxing on all the beaches. We hit the jack pot on beach glass. I think we brought home a half of cooler full. We had kayaks to use to go around the island and a quick trip over to Peak's Island for some groceries. If you are a tennis player, you will love the courts. They are a 2 minute walk from the Jail. We had 10 of us in all and there was room for plenty more. Every day we discovered something new on the island. There are some really cool forts and towers. The home is spectacular. It has everything you need. We spent every evening at the kitchen table playing games. The kitchen is a chef's dream. Every drawer and cupboard is stocked with everything you need to make a fancy gourmet meal, or keep it simple and grill hotdogs. If you read books, you will have a choice of 1000's to choose from. The beds were very comfortable, and no issues with having enough bathrooms. Plenty for everyone. The jails cells were a neat feature. If you have little ones, it's the perfect bedroom. The upstairs is a house of it's own. With it's own kitchen, living room, bath and bedroom. Everyone on the island was so friendly and accommodating. They made you feel very welcomed. It's the perfect place. I'm hoping to make this an anual trip. We laughed a lot, got to spend time with family that we had not seen for a long time. We will cherish the memories of Cushing Island. I can't stress enough, Love,Love,Love the Jail!!!
FAQs
How much does this house cost compared to others in Cushing Island?
The average price for a rental in Cushing Island is $677 per night. This rental is $0 less expensive than the average.
Is parking included with this house?
Parking is not specified as an available amenity at Refurbished Brick, Waterfront Home on Cushing's Island.. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Refurbished Brick, Waterfront Home on Cushing's Island. pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Refurbished Brick, Waterfront Home on Cushing's Island.?
We found 8 amenities for this rental. This includes pets allowed, kitchen or kitchenette, internet / wifi, laundry, and balcony or patio.
Cushing Island travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Keep exploring
- Kauai Villas
- Orlando Villas
- Kiawah Island Villas
- Miami Beach Villas
- Kissimmee Villas
- North Naples Villas
- Florida Keys Villas
- Phoenix Villas
- Los Angeles Villas
- St Petersburg Villas
- Palm Desert Villas
- Miami Villas
- Las Vegas Villas
- Venice Villas
- Key West Villas
- Palm Springs Villas
- Lake Tahoe Villas
- Hollywood Hills Villas
- Seabrook Island Villas
- South Lake Tahoe Villas
- Pocono Mountains Villas
- Scottsdale Villas
- Myrtle Beach Villas
- Hilton Head Island Villas
- Marco Island Villas
- North Miami Villas
- Sanibel Island Villas
- West Palm Beach Villas
- Fort Myers Beach Villas
- Haines City Villas
- North Las Vegas Villas
- Destin Villas
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals