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Entire home

Steps leading up to the deck that overlooks Spring Cove

Your view from the deck. This is Spring Cove with Whitehead Passage beyond.

The upstairs master bedroom suite spans the entire footprint of the main house.

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms4 bathroomsSleeps 10

Popular amenities

Barbecue grill

Washer

Outdoor space

Pet-friendly

Kitchen

Dryer

Check-in time

5:00 PM

Check-out time

10:00 AM

Explore the area

Portland, ME

Sand Beach6 min drive
State Theatre28 min drive
Thompson's Point32 min drive

Most relevant reviews

10/10 Excellent

Wonderful stay, beautiful island, incredibly thoughtful hosts!

Tom Q.

Jun 12, 2022

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

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Ocean view

Ocean view

Kitchen

Washer

Dryer

House Rules

Check in after 5:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

(Friendly!) dogs only

Smoking

Smoking is not permitted

Important information

You need to know

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

About the area

Portland

Located in Portland, this holiday home is by the ocean. State Theatre and Thompson's Point are cultural highlights, and travellers looking to shop may want to visit Maine Mall. Children's Museum and Theatre of Maine and Happy Wheels Skate Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Portland, ME

What's nearby

Sand Beach - 6 min drive
State Theatre - 28 min drive
University of Southern Maine - 29 min drive
East End Beach - 31 min drive
Thompson's Point - 32 min drive

Getting around

Portland Transportation Center - 38 min drive

Restaurants

‪DiMillo's On the Water - ‬27 min drive
‪Luke's Lobster Portland Pier - ‬27 min drive
‪Brickyard Hollow Brewing Company - ‬27 min drive
‪The Porthole - ‬27 min drive
Twelve

Frequently asked questions

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

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

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 0.1 mi (0.1 km) from Casco Bay and within 6 miles (10 km) of Umbrella Cover Museum and Fifth Maine Museum. House Island and Eastern Promenade are also within 6 miles (10 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.6/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Tom Q.

12 June 2022

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

Love it!

Wonderful stay, beautiful island, incredibly thoughtful hosts!

Stayed 9 nights in Jun 2022

10/10 Excellent

Simon K.

25 June 2021

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

10/10 Excellent

John B.

17 June 2021

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

10/10 Excellent

Tom Q.

6 June 2021

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

10/10 Excellent

Kate R.

28 Aug 2020

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

10/10 Excellent

Leslie H., Atlanta, GA

26 Aug 2018

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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Chris B., Orlando

6 Sept 2013

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!

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Allison R.

3 Sept 2013

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!

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Mark B., Maine

8 Aug 2013

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.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

21 Sept 2012

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...

This review was submitted before 2018 and has not been verified.

10/10 Excellent

30 Aug 2012

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!

This review was submitted before 2018 and has not been verified.

10/10 Excellent

26 Aug 2011

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.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Dana W., Petaluma, CA

16 July 2011

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!

This review was submitted before 2018 and has not been verified.

10/10 Excellent

15 July 2011

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!!!