Entire home
Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
Beachfront cottage for sun and fun
Photo gallery for Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families





Reviews
9.8 out of 10
Exceptional
5 bedrooms 2+ bathrooms Sleeps 14 223.0 sq m
Popular amenities
Explore the area

Peaks Island, ME
- Place, Casco Bay Lines Ferry Terminal27 min drive
- Place, State Theatre28 min drive
- Place, Sand Beach46 min drive
- Airport, Portland, ME (PWM-Portland Intl. Jetport)35 min drive
Rooms & beds
5 bedrooms (sleeps 14)
Captain's Quarters Loft
2 Double Beds
Captains Quarters Master Bedroom
1 King Bed
Catain's Quarters 2nd Bedroom
1 Queen Bed
Main House 2nd Bedroom
1 Queen Bed
Main House 3rd Bedroom
1 Single Bunk Bed
Main House Master
1 King Bed
2 bathrooms, 1 half bathroom
Captain's Quarters
Toilet · Shower only
Main House First Floor Bathroom
Toilet
Main House Upstairs Bathroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden
Dining area
About this property
Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
Cindy's Place is a hidden gem located on the rocky shoreline of Peaks Island overlooking the Casco Bay and the Portland skyline, House Island, and Fort Gorges. The property is located a quarter mile from the passenger ferry, the Inn on Peaks, the Downfront ice cream shop, and two restaurants. Within a half mile is the Post Office, Hannigan's Market, a third restaurant, and other Island businesses, including outfitters for renting bikes, golf carts, kayaks, and paddleboards. On the property you will find the Main Cottage located 12 feet from the water; the Captain's Quarters, a separate cottage with 2 bedrooms, a large sleeping loft, and a full bathroom and kitchenette; two patios with tables, chairs, and umbrellas overlooking the water; access to the rocky shoreline; and a beautifully landscaped yard. The Main Cottage was fully renovated in 2015 and includes a full kitchen, a full bath upstairs, a main-level half bath, a laundry area, a coffee and wine bar, and an airy open-concept main level. Upstairs are 2 bedrooms, each featuring a queen bed, chest of drawers, and television, and 1 bedroom containing a twin over full bunk bed with storage drawers underneath. Each of the queen bedrooms has access to a large furnished deck overlooking Casco Bay. The Captain's Quarters is an open-concept space with a kitchenette (including a sink, refrigerator, and Keurig coffee machine), a full bath, one queen bedroom, one king bedroom, and a sleeping loft with two queen beds.
The Island offers an array of activities, from walking or jogging the three-mile seashore perimeter to biking, kayaking, paddle boarding and sailing to visiting the historic Fifth Maine Regiment Museum. If your plans include the mainland, the restaurants, shops, tour operators and landmarks of Portland's lively waterfront district are only a 15 minute ferry ride away.
Casco Bay Lines operates passenger and car ferries all day from Monday through Sunday, along with narrated tours of the Bay and it's Islands. Visit for more information on the ferry schedule.
All Cindy's Place rentals include the Captain's Quarters unless otherwise stipulated. The rental price will not be adjusted for groups who choose not to use the Captain's Quarters.
The Island offers an array of activities, from walking or jogging the three-mile seashore perimeter to biking, kayaking, paddle boarding and sailing to visiting the historic Fifth Maine Regiment Museum. If your plans include the mainland, the restaurants, shops, tour operators and landmarks of Portland's lively waterfront district are only a 15 minute ferry ride away.
Casco Bay Lines operates passenger and car ferries all day from Monday through Sunday, along with narrated tours of the Bay and it's Islands. Visit for more information on the ferry schedule.
All Cindy's Place rentals include the Captain's Quarters unless otherwise stipulated. The rental price will not be adjusted for groups who choose not to use the Captain's Quarters.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Ocean view
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items and take out the rubbish
Start a load of sheets prior to leaving.
Failure to complete these may result in a negative review from the host.
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Peaks Island
Located in Peaks Island, this cottage is in the city centre and on the beach. Thompson's Point and Umbrella Cover Museum are cultural highlights, and some of the area's attractions include Maine Narrow Gauge Railroad Company and Museum and Portland Observatory. Travelling with kids? Consider Bayside Bowl, or check out an event or a game at Merrill Auditorium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Peaks Island, ME
What's nearby
- Casco Bay Lines Ferry Terminal - 27 min drive - 5.2 km
- Cross Insurance Arena - 27 min drive - 5.6 km
- State Theatre - 28 min drive - 6.3 km
- East End Beach - 29 min drive - 6.6 km
- Sand Beach - 46 min drive - 8.5 km
Getting around
Restaurants
- North43Bistro - 33 min drive
- Scratch Baking Co. - 33 min drive
- Second Rodeo Coffee - 32 min drive
- A&C Soda Shop - 32 min drive
- DiPietro's - 32 min drive
Frequently asked questions
About the host
Hosted by Greg Carter

My brother and I purchased this family home from our uncles 3 years ago. This property has been in our family for 80 years. We have recently upgraded and renovated the entire thing to accommodate our two families occupancy at the same time. This house has huge sentimental value to us as this was where we summered as kids. Due to life however, our jobs have taken both my brother and I out of Maine and to Connecticut and North Carolina. Because of this we are unable to reside in this property for the entire summer. So we decided to rent this to people and allow them to experience what we have known for years, this location can transport you to a place of serenity and wonder.
Why they chose this property
Simply put, there are few summer homes in Maine that rival the location of Cindy's Place. Situated beside a classic rocky Maine beach only steps from the water, our home enjoys expansive views of Casco Bay, House Island, and Fort Gorges. Cindy's Place is within easy walking distance of many of the Island's landmarks including Sandy Beach, the three-mile seashore perimeter path, and the Fifth Maine Regiment Museum. You will also have easy access to the Island's grocery store, restaurants, and shops, including Downfront, Peaks Island's beloved ice cream and souvenir shop, and the ferry landing, which is a short 15-minute ferry ride from the restaurants, shops, and tour opportunities of the Portland waterfront district.
What makes this property unique
With two cottages on site, Cindy's Place is perfect for families and friends looking for a vacation property that allows them to both spend time together and spread out and enjoy their own space. The property's proximity to the water and all of the amenities of the Island means that it's never a challenge to reach out and enjoy all that summer in Maine has to offer, whether that means beachcombing, swimming, sailing, biking or setting off to explore the mainland.
Languages:
English
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