Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
Cottage in Peaks Island, ME
14 guests · 6 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
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.
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
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Peaks Island, ME
Reviews
10.0
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.
10.0
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!
10.0
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.
10.0
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.
10.0
Everyone loved the location!
House was perfect!
10.0
We were guests at a wedding at the TEIA and it was so great to stay on Island. We had our own parking spot at the house and still room for our rented golf carts. Location was fantastic to ferry and only a 10 minute golf cart cruise to venue. Views were amazing from both houses and we had plenty of room to gather. Greg was very accessible and responsive to all our questions. Cindy's place is a very special place and I'm already trying to figure out when we can return.
10.0
Everything at Cindy’s place was absolutely perfect!
10.0
The location is amazing. Views in every direction, sailboats passing by and keeping time with the ferry. Quiet, peaceful, but a quick walk to town. This property is ideal for a family group. We had the grownup’s house and the parents and kid’s house. Plenty of room for gathering and sunset meals by the water. Remarkably well appointed with everything from toys for the beach to a futuristic toaster! Very comfortable and thoughtfully designed. We were there for a wedding right next door at the Lion’s Club so couldn’t have been better. Thank you, Greg!
10.0
A group of 10 of us stayed for a weekend at Greg’s place - fantastic location right on the water, only minutes to walk to the beach, ferry, golf cart rentals, and a restaurant with unbelievable lobster rolls. Fantastic weekend - definitely will be back!
10.0
Beautiful property literally on the water. Everything was exactly as listed or better. We will be back. Thanks for having us!
10.0
My husband and I are Portland residents but we needed a larger space to host our family for a long weekend. Cindy’s place was gorgeous and functional. The view is everything you imagine when visiting maine. My dad got a kick out of watching the lobsterman drop their traps in the morning and my mom was awed by the gorgeous sunset each night. The two separate houses were perfect so the grandparents could sneak away for some quiet time. There is so much to do right there. The kids went hunting for sea glass on the little beach and the adults had a glass of wine on the patio. We are big cooks, and the kitchen and grill had everything you could need for some awesome family meals. Thank you for hosting my Family and I, it was exceptional.
10.0
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.
5.0
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.
5.0
Highly recommend. Beautiful place!
5.0
Very smooth process and great and rare upgraded property for rent on Peaks. The main room is like being on a boat in the ocean with spectacular sunset views. Fully equipped and very nice outdoor seating.
I wasn’t crazy about the request to wash sheets and towels when check out time was 10 am. One of the bedrooms in the main cottage is bunk beds that will only work for v small children. The property is adjacent to an events hall so is likely to be used and loud on weekends in summer; this did not disturb us but worth noting.
5.0
We had a fantastic stay at “Cindy’s Place.”
We were on the island for a family wedding and had 5 adults and 5 teens. The location could not be more perfect- close to the ferry, restaurant’s and shops with views of Portland and gorgeous sunsets. As for the houses, they are updated, clean, and well stocked with comfortable beds and linens. There are multiple places to gather including a neatly designed patio overlooking the water and an upper deck off the main house. When the tide is out there’s plenty of beach for gathering sea glass and other ocean treasures. Really can’t say enough about this house- we hope to visit again!
5.0
Perfect rental for 4 couples. Very well appointed. Views are unbelievable .
5.0
My extended family (4 young adult cousins, several aunts and uncle and a grandmother) recently stayed at this gorgeous ocean front compound and I’m not sure I have words to express just how wonderful this place is. . . But I will try! We have been renting on Peaks for a number of years and this was by far the best place ever - as others have noted - and the first time for us that reality far surpassed the online photos. Everything seemed much bigger and more beautiful than the photos. In the main house, the feeling of floating over the water is almost fantasy-like. From inside in the glassed- in living room, from the upstairs deck literally hanging over the water, from the large stone patio, and even from the living room and loft of the Captain’s Quarters - one can while away the time just watching the constant boat activity surrounding the island, viewing seacoast birds, and even just watching the weather change, with binoculars (kindly provided) handy. There is a small beach (sandy at low tide) where we were able to launch the kayaks we brought with ease, and comb for shells and interesting rocks. The beautifully constructed large stone patio - built right into the small hillside between houses and right off the kitchen of the main house, has 4 sunset viewing “chairs” built right into its wall, along with the large table and chairs and a few Adirondack chairs in their own little nook. So thoughtfully designed for the NIGHTLY live color show that comes free of charge as you watch the sun sink into the ocean. We have a long list of activities we enjoy on Peaks, and all are easily accessed from the house - biking the circumference of Peaks and finding new little dirt lanes to explore, hiking in the preserve in the center of the island, exploring the old WWII battery and watchtower, jumping off the ferry pier (if one can summon the courage!), buying lobsters from Forest City Seafood - right on the dock, and our new tradition - spending a live-music filled afternoon of laughing and dancing at Raggae Sunday at Jones Landing near the pier - esp fun this year now that our young adults can sip drinks with us! The lawn space of this property is quite expansive for playing outside, and the landscaping is very nicely done. The hosts are responsive and very easy to work with. There is just nothing bad to say. We LOVED it and have already booked for next summer. Highly recommend!
5.0
The 2 buildings game us the ability to put the young adults in the upper quarter with the remaining in the main house. The quality of the buildings were second to none and the outside landscaping was all anyone could ask for. Nice Job Greg Carter!!!!!!!!!!!!! Facing Portland and the closeness to he ferry was a bonus.
5.0
Great stay, great communication with the owner, home has all you can ask for including an incredible view and property!
5.0
This is a beautiful property on Peaks Island with an amazing view! Greg is a great host and is very responsive. We’ve been visiting Peaks for over 30 years and this was the best house, by far, in a perfect location. We would love to return!
5.0
Went smoothly. Enjoyed biking around Island. View from both houses picturous.
5.0
We rented both houses for my family, they were in my opinion the nicest on the island!! Great views, appeared new, very clean and owner was very accommodating. Close to the downtown area. My soon to be wife and I had our “first look” on the shoreline at the house, very pretty!!!
5.0
Wonderful, perfect for our larger group
5.0
The property including the two houses and the little beach is a real gem. We really enjoyed being right on the water watching all the sailboats and other boats zigzagging around the bay, the sunsets, the clouds and changing light throughout the day. Everything about the houses and amenities including the numerous outdoor sitting areas and furniture is first class.
5.0
Cindy's Place on Peak's Island, ME is the perfect spot for experiencing island life. It's close to the main street with shops and grocery, but also far enough to feel like your own private hideaway. Nestled right on the rocks of Casco Bay, you can sit and watch the boats come and go and experience stunning sunsets every night. The landscaping is beautiful and sitting outside is like being in a park. The two houses were perfect for a group or family that likes some space. Both were very clean and well-equipped.
The owner was very nice and extremely easy to communicate with and responsive whenever I had questions, both before we left and during our stay. The main house is well equipped with kitchen items and its own coffee/drink bar. The owner was generous with leaving things from prior guests that we could also use- it's nice to have spices, ketchup, etc. The upper cottage had its own kitchenette as well and was well stocked- a great place to wake up and have a cup of coffee before joining the others in the main house. The beds were very comfortable as well!
In fact, the house was so nice that we rarely left it. We only went into Portland twice! They had 2 bikes we could use and a kayak. We walked around the island every day and met locals wherever we went. We rented a golf cart from Mike's Carts for the week so we could explore the island. We ate ice cream and watched the ferry. We ate lobster and more lobster!
I highly recommend staying at Cindy's Place. It's a gorgeous place to spend your vacation!! We will definitely be back!
5.0
The property is a few minutes walk from the Peaks Island ferry, and is feet from the water. The main living room is surrounded by amazing views; we spent a lot of time just relaxing and watching the waves. There are tables to sit at outside, and a hammock, and comfy chairs and sofas inside. (For the extra-hot day we got, the AC inside was well appreciated).
The second "Captain's Quarters" house was perfect for a family with kids that was part of our group, to keep naptime from being disrupted by everyone else (or vice versa).
All of us very much enjoyed our stay and hope to return in the future!
5.0
Perfect property for a family weekend. The 2 houses were absolutely beautiful with a perfect view. Loved every minute!
5.0
This is a beautiful property with 180-degree views of Casco bay and a bit of sandy beach at low tide. I would go on about the wonderful layout and amenities inside (everything is so nice, right down to the oversize beach towels in the downstairs bathroom) but we spent almost the entire week on the patio or outdoor decks. Our children spent hours exploring at the water's edge and on the rainy days, played with the toys found in cabinets inside. We took sunset kayak and canoe rides out to a tiny spit of island close by and puttered around the back shore on a golf cart (arrange in advance for a weekly rental from one of two golf-cart rental places on the island). We had friends for dinner on the large and gorgeous patio, and had a surprise few drinks left for us in the drinks fridge by whoever the kind prior guests were.
10.0
The cottage was renovated earlier this year and the owners did an amazing job. The cottage is beautifully appointed and equipped and the views are breathtaking. It's just a short walk from the ferry and you can see the ferry come and go, as well as all the other harbor activity. Portland and other islands are visible from the front decks and you see sailboats, lobster boats and even cruise ships! The living areas are light and comfortable and the downstairs areas as well as the two main bedrooms upstairs look out on the water view. The floor in the upstairs bathroom is even heated....a delightful luxury on a cold morning. All of the appliances are new (including a wine cooler) and the furniture is island casual and conducive to relaxing and enjoying a quiet vacation. The island is not large and provides easy walking and exploring. There are also bicycles and golf carts available for rent. That said, Portland is just a 20 minute ferry ride away so, if you want more action or an afternoon or evening about town, it's an easy option. We had a GREAT time!
PW in Chesapeake Beach, MD
FAQs
How much does this cottage cost compared to others in Peaks Island?
The average price for a rental in Peaks Island is R 8,824 per night. This rental is R 6,663 above the average.
Is parking included with this cottage?
Yes, parking is listed as an 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 10 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
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