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

Peaks Island, Maine
$993 avg/night
Minimum Stay 3 Nights
Bed 5

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 14

Max Sleeps

Night 3 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2400 Sq Ft (223 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Electric Kettle Lobster/crab Pot Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Barbecue Grill Garden Outdoor Furniture Yard
  • BATHROOMS

    2.5 Bathrooms Hair Dryer Shower Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Fishing Nearby Kayak On Site Power Boating Nearby Sailing Nearby Swimming Nearby Whale Watching Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books DVD Player Games Stereo Video Library Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games Children's Toys Highchair
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near The Ocean Near The Sea On The Bay On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Availability

Review Review

  • laura l.

    Submitted Oct 12, 2025

    Stayed Oct 2, 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!

  • Hillary L.

    Submitted Sep 28, 2025

    Stayed Sep 25, 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

  • Kassie S.

    Submitted Jun 5, 2025

    Stayed Jun 1, 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!

  • Marlena L.

    Submitted Jun 3, 2025

    Stayed May 23, 2025

    The house is absolutely beautiful and the location can’t be beat. Perfect place to spend the weekend!

  • Rhonda Y.

    Submitted Sep 9, 2024

    Stayed Sep 6, 2024

    My husband, daughter and her friend, along with my sisters in law and brother in law stayed at Cindy's place for 3 nights. It was more beautiful than the pictures showed and very well appointed with everything you need. We loved the privacy and convenience of the location and also having two houses. My daughter and friend loved the loft and stayed in the Captains quarters with the extended family while my husband and I enjoyed the main house. I slept with the slider and window open to hear the ocean waves and smell the salty air; I slept like a baby. We were able to walk along the beach/rocks and make our way to picnic point to explore that sweet little island too. Greg was easy to communicate with and we hope to get back to Cindy's place again in the coming years. Greg, well done preserving your family's home and thank you for sharing it with us.

  • John H.

    Submitted Sep 2, 2024

    Stayed Aug 16, 2024

    5-star property with room for 14 adults and children. Right on the water, all amenities, and a 5 minute walk from the Ferry. You cannot do better than to select Cindy's Place for your next family vacation.

  • Nancy R.

    Submitted Aug 31, 2024

    Stayed Aug 24, 2024

    What a fantastic property for an extended family, 70yo grands, 2 couples, 7, 8, 9 yo kids. 2 houses made it easy to have get-away space, plus a place to gather and cook together. Beautiful views with constantly changing bay. Kids especially loved exploring the adjacent beach during low tide. Everyone was able to climb down to it. Nice short walk into town. Everyone said they wished we had a second week. Things to know: live, loud, band in town Saturday til 10:30 and Sunday til 8. Not terrible but glad it wasn’t 6 days. After that it was a very quiet and peaceful location. A sloped hill leads from parking lot to main house but there is a little red wagon to load and pull your stuff. The main house was comfortable for 2 couples and one kid. The 3rd bedroom is small and would be tight for a couple. Owner is very responsive with info and addressing issues. We all wished for more time here.

  • Brian B.

    Submitted May 27, 2024

    Stayed May 23, 2024

    We celebrated our wedding on Peaks Island Inn and the house was perfectly located for us. We were able to walk into town. Our friends and family could stop by and sit by the water. Could’ve been better!

  • paul m.

    Submitted Oct 17, 2023

    Stayed Oct 13, 2023

    We were up for our son's wedding in October at Peaks Island Inn. This was the absolute perfect VRBO rental for the occasion. Plenty of open concept room with beautiful views out over the bay. The outdoor decks are inviting and comfortable, the indoor spaces are warm and open. Distance to the Inn is about 1/4 mile, so an easy walk for those that wish, but there is also plenty of parking at both the inn and the VRBO if needed. Kitchen is well stocked, bathrooms are clean, washer and dryer on premise. We had plenty of wedding guests on the Island, many of whom came over for day after wedding brunch. I guess that is when you realize you have the nicest VRBO on the island... because everyone at a different place says so when they visit :) You will not go wrong with this VRBO, and if you are trying to figure which one to rent, this is it. The pictures on line are nice, the actual experience is better. Some VRBO's post nice pictures, and when you get there the unit does not hold up to the online presentation. This is the opposite, even better than you anticipate. Owner is very nice, receptive to all questions, and clearly takes great pride in both the home and your positive experience.

  • Liz and Joe G.

    Submitted Sep 9, 2023

    Stayed Sep 1, 2023

    This was a great property for our group. The views from the house are stunning and the whole property is very well maintained. We appreciated the comfortable seating in both houses and the beds were also comfortable. The location is easily walkable from the ferry. We had no need for a car while there. A few quirks—none of the bedrooms in the main house have closets or any place for hanging clothes so pack accordingly. Check in/out instructions were a bit more arduous than what is typical, You do have to make the beds when you arrive and they ask that you wash and dry sheets, towels if possible. We did the best we could. Overall a wonderful property.

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Total

Includes taxes and fees
$1,058+
View details