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Refurbished Brick, Waterfront Home on Cushing's Island.

Photo gallery for Refurbished Brick, Waterfront Home on Cushing's Island.

A dining area with a wooden table and chairs, large windows, and a television mounted on the wall.
A living room with a sofa, chairs, a coffee table, a lamp, a bookshelf, and a large window with curtains.
An attic room with a sloped ceiling, a television, a desk, and a chair.
A covered porch with wooden flooring and white railings, featuring several chairs and tables.
A two-story brick house with a front porch, a chimney, and a well-maintained lawn.

Reviews

10 out of 10
Exceptional

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
Sleeps 10•5 bedrooms•6 beds

Popular amenities

  • Dog-friendly
  • Kitchen
  • Washing machine
  • Barbecue
  • Dock
  • Free Wi-Fi

Explore the area

View map
Portland, ME
  • Place, Big Beach
    ‪11 min walk‬
  • Place, Cross Insurance Arena
    ‪58 min drive‬
  • Place, State Theatre
    ‪59 min drive‬
  • Airport, Sanford, ME (SFM-Sanford Seacoast Regional)
    ‪95 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

Bunk House

2 Single Beds

4 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub · Toilet

Bathroom 4

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Garden
Dining area

About this property

Refurbished Brick, Waterfront Home on Cushing's Island.

'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

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House Rules

Check in after 5:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
(Friendly!) dogs only
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 344204vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Portland

Located in Portland, this holiday home is by the ocean. State Theatre and Portland Head Light are notable landmarks, and the area's natural beauty can be seen at Thompson's Point and Higgins Beach. Children's Museum and Theatre of Maine and Happy Wheels Skate Center are also worth visiting. Discover the area's water adventures with kayaking, windsurfing and power boating nearby, or enjoy the great outdoors with hiking.
View more Holiday homes in PortlandOpens in a new window
Map
Portland, ME

What's nearby

  • Big Beach - 11 min walk - 1.0 km
  • Cross Insurance Arena - 58 min drive - 6.1 km
  • Portland Museum of Art - 58 min drive - 6.5 km
  • Merrill Auditorium - 59 min drive - 6.4 km
  • State Theatre - 59 min drive - 6.8 km

Getting around

  • Portland Transportation Center - 38 min drive

Restaurants

  • Second Rodeo Coffee
  • Luke’s Lobster
  • The Porthole
  • ‪North43Bistro - ‬33 min drive
  • DiMillo's On the Water

Frequently asked questions

Is Refurbished Brick, Waterfront Home on Cushing's Island. pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Refurbished Brick, Waterfront Home on Cushing's Island.?

As of 10 Aug 2026, prices found for a 1-night stay for 2 adults at Refurbished Brick, Waterfront Home on Cushing's Island. on 13 Nov 2026 start from AU$6,723, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Refurbished Brick, Waterfront Home on Cushing's Island.?

Check-in begins at 5:00 PM.

What time is check-out at Refurbished Brick, Waterfront Home on Cushing's Island.?

Checkout is at 10:00 AM.

Where is Refurbished Brick, Waterfront Home on Cushing's Island. located?

Situated by the ocean, this holiday home is steps from Casco Bay and within 6 mi (10 km) of Umbrella Cover Museum and Fifth Maine Museum. House Island and Eastern Promenade are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Archival

10/10 Excellent

Allison R.

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!
Verified review

10/10 Excellent

Leslie H.

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.
Stayed 7 nights in Aug 2018
Verified review

10/10 Excellent

Linda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Time

This was our second time visiting the Jailhouse. The house is well equipped for all of us to spend time together but also have time to ourselves. The kitchen well equipped with two ovens and two dishwashers. It had everything our large family needed. The upstairs living space was great for my husband and I to have peace and quiet. A drawback was a few hot days made the upstairs apartment pretty hot and fans could not keep up. The outside shower and hammock were a nice addition since our last visit. The island is magical and Casco Bay is beautiful. We kayaked, enjoyed hunting for sea glass on the beaches, and enjoyed discovering the island through many fairy tale like trails. All of us explored as we saw fit and met for family dinners to share our stories. Sunsets on the dock were a great end to the days. Every one of us aged 16-50’s enjoyed this vacation and we plan to return. Our two dogs also enjoyed their stay!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Tom Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love it!

Wonderful stay, beautiful island, incredibly thoughtful hosts!
Stayed 9 nights in Jun 2022
Verified review

10/10 Excellent

Simon K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

Tom Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love it.

Magical island, spacious and well-equipped home, and wonderful hosts. Could not have been better.
Stayed 9 nights in May 2021
Verified review

10/10 Excellent

Kate R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

What a magical island! We all had such a good time walking and kayaking and lounging every day.
Stayed 7 nights in Aug 2020
Archival

10/10 Excellent

Chris B.

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!
Archival

10/10 Excellent

Mark B.

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.
Archival

10/10 Excellent

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...
Archival

10/10 Excellent

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!
Archival

10/10 Excellent

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.
Archival

10/10 Excellent

Dana W.

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!
Archival

10/10 Excellent

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!!!

About the host

Your host

Host profile image
This is a family-owned property.

Why they chose this property

Our family has spent summers on Cushings Island for over 60 years.
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