Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families

Top rated by guests
Arial View of House
Kitchen view as Main Cottage is entered
Kitchen main cottage
Coffee bar with beverage fridge.
Captian's Quarters Dining Room
review stars
9.8Outstanding
(46 Ratings)
"We stayed 5 nights for our daughter's wedding. Family enjoyed sitting on the patio watching the activity in the bay. My only suggestion for the host would be to stock coffee pods and water at each bui..."
laura l.
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9.8 / 10
Outstanding(46 Ratings)

Cottage in Peaks Island, ME

14 guests · 5 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this cottage rental

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.

Amenities at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families

Non-smoking
No pets allowed
Family friendly

Map of Peaks Island, ME


Ratings and reviews

9.8 / 10
Outstanding(46 Ratings)
10 / 10Outstanding·Oct 2025
We stayed 5 nights for our daughter's wedding. Family enjoyed sitting on the patio watching the activity in the bay. My only suggestion for the host would be to stock coffee pods and water at each building. Overall, a great experience. I would recommend for you stay!
10 / 10Outstanding·Sep 2025
Words cannot properly describe how beautiful this house was. The host was very communicative and accommodating. This house was a dream come true for our girls trip
10 / 10Outstanding·Jun 2025
This property is gorgeous! The location and set up was perfect for our family of 8. Greg the host was welcoming and accommodating, going as far as making recommendations for our stay. We will be visiting the island again!
5 / 10·Sep 2021
Cindy’s Place is wonderful and was a perfect spot for 4 good friends (all women) to get together. Both cottages are lovely, clean, and well-equipped. We didn’t have a single problem during our stay and we’re looking forward to coming back. The owner was a pleasure to work with…responsive, informative, and kind. Peaks Island is a great option place if you’re visiting Portland or the surrounding area. Quiet, quaint, and charming. And, the ferry to Portland was easy and on schedule. I highly recommend Cindy’s Place and Peaks Island to anyone planning a trip to Maine.

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families pet friendly?

Unfortunately, this cottage is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.