Refurbished Brick, Waterfront Home on Cushing's Island. | House in Portland

Q: How much does it cost per night to stay in Portland house?

Best-rates for the Portland house starts from $657 per night with includes Child Friendly, Ocean View, Security/Safety, Bedding/Linens, Laundry, Hot Tub, Kitchen, Pet Friendly, View, Balcony/Terrace, Sports/Activities, Wellness Facilities, Barbecue/Outdoor Cooking, Entertainment, Internet with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

10.0 (15 Reviews) | Pet Friendly 5 Bedrooms 4 Bathrooms 10 Guests

Portland House | Refurbished Brick, Waterfront Home on Cushing's Island.

5 Bedroom House in Portland

'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

Refurbished Brick, Waterfront Home on Cushing's Island is located in Portland. Refurbished Brick, Waterfront Home on Cushing's Island provides accommodation, featuring Child Friendly, Ocean View, Security/Safety, among other amenities. This House features Child Friendly, Ocean View, Security/Safety, to make your stay a comfortable one.

Refurbished Brick, Waterfront Home on Cushing's Island has 5 Bedrooms , 4 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Portland has interesting places to visit. If you want to learn more about the House in Portland, such as places to visit and things to do nearby, you can check below to learn more.

Amenities

Pet Friendly
View
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in Check-in time starts at 5:00 pm minimum check-in age: 25

Check-out Check-out before 10:00 am

Child Policy Children are welcome.

Pet Policy 2 total pets note from host: (friendly!) dogs only pets allowed service animals are welcome, and are exempt from fees welcoming dogs only

Other Policy 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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

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Reviews

Linda B. Jun 29, 2025 05:25:09 AM

Summary: 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!

Tom Q. Jun 13, 2022 06:35:47 AM

Summary: Wonderful stay, beautiful island, incredibly thoughtful hosts!

John B. Jul 2, 2021 11:00:57 AM

Summary: 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!!

Simon K. Jun 26, 2021 02:35:28 AM

Summary: 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

Tom Q. Jun 19, 2021 10:44:12 AM

Summary: Magical island, spacious and well-equipped home, and wonderful hosts. Could not have been better.

Kate R. Aug 28, 2020 08:54:46 PM

Summary: What a magical island! We all had such a good time walking and kayaking and lounging every day.

Leslie H. Aug 26, 2018 11:17:27 PM

Summary: 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.

Chris B. Sep 7, 2013 12:20:52 AM

Summary: 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!

Allison R. Sep 3, 2013 11:20:02 PM

Summary: 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!

Mark B. Aug 9, 2013 01:40:16 AM

Summary: 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.

FAQ's

Is this Portland house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Portland house have a swimming pool?

No, this Portland house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Portland house?

Best-rates for the Portland house starts from $657 per night with includes Child Friendly, Ocean View, Security/Safety, Bedding/Linens, Laundry, Hot Tub, Kitchen, Pet Friendly, View, Balcony/Terrace, Sports/Activities, Wellness Facilities, Barbecue/Outdoor Cooking, Entertainment, Internet with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Portland house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Portland house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Portland house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Portland house?

Based on the information reported by the owner or manager, the Portland house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Portland house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Portland house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability

Nightly rates from:

US $657