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Refurbished Brick, Waterfront Home on Cushing's Island."""

Bedrooms 5
Property type house
Minimum Stay 1 - 7 nights


About the property

House, 5 Bedrooms + Bunk Area, 4 Baths, (Sleeps 10-13)

'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

More Details

Member since: 2011
Speaks English
Response time:
Within 2 days
Response rate:
Calendar last updated:
18 March, 2018

About The Owner

This is a family-owned property.

The Owner purchased this house in 2011

Why The Owner chose Portland

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


Accommodation and facilities for this holiday house in Portland in Cumberland County

Property Type:
  • house
  • Self-catering
House Rules:
  • Check-in: 16:00 / Check-out: 11:00
  • Max. occupancy: 13
  • pets considered ...
  • children welcome
  • non smoking only
Location Type:
  • Ocean View
  • Oceanfront
  • Clothes Dryer
  • Linens Provided
  • Living Room
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator ...
  • Hob
  • Toaster
  • Dining Area
  • 4 Bathrooms
  • Bathroom 1 - Toilet , Bath with Shower
    Bathroom 2 - Toilet , Shower Enclosure
    Bathroom 3 - Toilet , Bath (no shower)
    Bathroom 4 - Toilet , Shower Enclosure , Jacuzzi
  • 4
  • 5 Bedrooms, Sleeps 13
  • Bedroom 1 - 1 Large Double Bed
    Bedroom 2 - 1 Large Double Bed
    Bedroom 3 - 1 Large Double Bed
    Bedroom 4 - 2 Single Bed
    Bedroom 5 - 2 Single Bed
    Bunk House - 2 Single Bed
  • Additional Beds - 3 singles (actual WWI jail cells!)
  • Books
  • DVD Player
  • Games
  • Stereo
  • Toys
  • Boat ...
  • Terrace ...
  • Kayak / Canoe ...
  • Garden ...
  • Barbecue
  • Tennis ...
Pool / Spa:
  • Communal Pool ...
Leisure Activities:
  • Boating
Sports & Adventure Activities:
  • fishing
  • hiking
  • Kayaking
  • sailing
  • swimming
  • tennis
  • wind-surfing


Exceptional! 5/5 -
(8 traveller reviews)

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Refurbished Brick, Waterfront Home on Cushing's Island.
average rating of 5.0 based on 8 reviews

Wonderful Week!

  • 5 of 5

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!

  • Review Submitted: 04-Sep-2013
  • Date of Stay: July 2013
  • Source: VRBO, from HomeAway
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4 0

A Week We'll Never Forget!

  • 5 of 5

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!

  • Review Submitted: 30-Aug-2013
  • Date of Stay: August 2013
  • Source: VRBO, from HomeAway
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2 0

Perfect Vacation Rental

  • 5 of 5

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.

  • Review Submitted: 06-Aug-2013
  • Date of Stay: June 2013
  • Source: VRBO, from HomeAway
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4 0

Wonderful Family Get-away

  • 5 of 5

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...

  • Review Submitted: 19-Sep-2012
  • Date of Stay: August 2012
  • Source: VRBO, from HomeAway
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1 0

Amazing Island Getaway!

  • 5 of 5

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!

  • Review Submitted: 26-Aug-2012
  • Date of Stay: July 2012
  • Source: VRBO, from HomeAway
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2 0
Fitchburg, MA

Peaceful Adventurous Family Vacation

  • 5 of 5

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.

  • Review Submitted: 24-Aug-2011
  • Date of Stay: August 2011
  • Source: VRBO, from HomeAway
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Prices & Availability

Prices for this holiday house in Portland, Maine

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
Low Season (Spring 2018)
1 May 2018 - 22 Jun 2018
7 night minimum stay
for 7 nights
High Season
23 Jun 2018 - 1 Sep 2018
7 night minimum stay
for 7 nights
Low Season (Fall 2018)
2 Sep 2018 - 3 Nov 2018
7 night minimum stay
for 7 nights

Additional pricing information

Cleaning Fee £180.52
Tax Rate 9.0%

60% deposit at time of booking, remaining 40% due two weeks before arrival.

Owner's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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