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

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

Arial View of House
Arial view from water of Main House, Captain's Quarters and Side Patio
Main House, Captains Quarters & Side Patio
Main House and Captain's Quarters from the Water
Arial View of House from Water (Pre Construction of New Captian's Quarters

Reviews

9.8 out of 10
Exceptional
5 bedrooms2+ bathroomsSleeps 142400 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Peaks Island, ME
  • Place, Umbrella Cover Museum
    ‪6 min walk‬
  • Place, Fifth Maine Museum
    ‪7 min walk‬
  • Place, Richard Boyd Art Gallery
    ‪8 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪37 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 Twin 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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you 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 trash
Start a load of sheets prior to leaving.
Failure to complete these may result in a negative review from the host.
The house(s) and property cannot be used for any type of function or gathering beyond the people staying at the property.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Peaks Island

Located in Peaks Island, this cottage is in the city center and on the beach. Umbrella Cover Museum and Richard Boyd Art Gallery are cultural highlights, and some of the area's attractions include Maine Narrow Gauge Railroad and Portland Observatory. Traveling with kids? Consider Bayside Bowl, or check out an event or a game at Merrill Auditorium. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Cottages in Peaks IslandOpens in a new window
Map
Peaks Island, ME

What's nearby

  • Umbrella Cover Museum - 6 min walk - 0.6 km
  • Fifth Maine Museum - 7 min walk - 0.6 km
  • Richard Boyd Art Gallery - 8 min walk - 0.7 km
  • Battery Steele - 3 min drive - 1.9 km
  • Battery Steele - 3 min drive - 1.9 km

Getting around

  • Portland Transportation Center - 41 min drive
  • Portland Intl. Jetport Airport (PWM) - 49 min drive

Restaurants

  • ‪Second Rodeo Coffee - ‬32 min drive
  • ‪Twelve - ‬27 min drive
  • ‪North43Bistro - ‬33 min drive
  • ‪Scratch Baking Co. - ‬33 min drive
  • ‪Angoor Wine Bar - ‬27 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families?

As of Mar 27, 2026, prices found for a 1-night stay for 2 adults at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families on Sep 7, 2026 start from $850, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families?

Check-out is at 10:00 AM.

Where is Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families located?

Located in Peaks Island, this beachfront cottage is in the city center and within a 10-minute walk of Casco Bay, Umbrella Cover Museum, and Richard Boyd Art Gallery. Casco Bay Lines Ferry Terminal and Fifth Maine Museum are also within 3 mi (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 44 out of 46 reviews
Rating 8 - Good. 1 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 1 out of 46 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

8/10 Good

Marlena L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect weekend getaway

The house is absolutely beautiful and the location can’t be beat. Perfect place to spend the weekend!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Hillary L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

laura l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Kassie S.

Liked: Check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

John H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Best Place to Stay in Portland

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.
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Martha C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Wedding

Everyone loved the location! House was perfect!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Brian B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Picture Perfect

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!
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Andrea N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house!!

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!!!
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

Amanda G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible location, updated property

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.
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Liz and Joe G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house on the water

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.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Rhonda Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just Wow!

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.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Nancy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful for family

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.
Stayed 6 nights in Aug 2024
Verified

10/10 Excellent

paul m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

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.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Katie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Weekend on Peaks

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.
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

Nancy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

Everything at Cindy’s place was absolutely perfect!
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

Eliza S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just book it!

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!
Stayed 7 nights in Sep 2022
Verified

10/10 Excellent

Tom M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Couldn’t ask for better

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!
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

Erik R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional

Beautiful property literally on the water. Everything was exactly as listed or better. We will be back. Thanks for having us!
Stayed 4 nights in Nov 2021
Verified

10/10 Excellent

Erin T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Staycation

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.
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property and great owner

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.
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Elizabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

Highly recommend. Beautiful place!
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Heather R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding weekend on Peaks!

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!
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Gerry N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends week.

Perfect rental for 4 couples. Very well appointed. Views are unbelievable .
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Melissa K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unforgettable Vacation

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!
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Laddie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

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.
Stayed 7 nights in Jul 2021

About the host

Hosted by Greg Carter

Host profile image
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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