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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

A two-story house with a balcony, surrounded by trees and rocks.
A room with a large window overlooking a body of water, a ceiling fan, and a dining table with chairs.
A dining area with a wooden table and white chairs, a bowl of apples, a coffee cup, and a microwave.
A room with a view of a body of water, a white sofa with anchor pillows, a white armchair with a crab pillow, and a blue patterned rug.
A modern two-story house with a balcony, a stone pathway, and a patio area with outdoor furniture.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Casco Bay

Popular amenities

  • Balcony or patio
  • On beach
  • Kitchenette
  • Toys
  • Barbecue grill
  • Air-conditioning

Explore the area

View in a map
Peaks Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Umbrella Cover Museum
    ‪8 min walk‬
  • Place, Fifth Maine Museum
    ‪8 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪41 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

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9.8 out of 10, Exceptional, (43 reviews)
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About the area

Peaks Island

Located in Peaks Island, this cottage is in the city centre and on the beach. State Theatre and Thompson's Point are cultural highlights, and travellers looking to shop may want to visit Maine Mall. Travelling with kids? Consider Maine Sports Hall of Fame and Maine Narrow Gauge Railroad. Kayaking, power boating and sailing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
View more Cottages in Peaks IslandOpens in a new window
Map
Peaks Island, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Umbrella Cover Museum - 8 min walk - 0.7 km
  • Fifth Maine Museum - 8 min walk - 0.7 km
  • Richard Boyd Art Gallery - 10 min walk - 0.9 km
  • Battery Steele - 4 min drive - 2.6 km

Getting around

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

Restaurants

  • ‪Luke’s Lobster - ‬27 min drive
  • ‪Brickyard Hollow Brewing Company - ‬27 min drive
  • ‪Twelve - ‬27 min drive
  • ‪Second Rodeo Coffee - ‬32 min drive
  • ‪Saltwater Grille - ‬33 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 is parking at Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families?

On-site 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?

Checkout 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 centre and within a 10-minute walk of Casco Bay, Umbrella Cover Museum and Fifth Maine Museum. House Island and Battery Steele are also within 1 mile (2 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 48 out of 50 reviews
Rating 8 - Good. 1 out of 50 reviews
Rating 6 - Okay. 0 out of 50 reviews
Rating 4 - Poor. 0 out of 50 reviews
Rating 2 - Terrible. 1 out of 50 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The views from both houses were absolutely beautiful. The view of the ocean and the sunset was absolutely gorgeous. The captain Quarter’s house was my favorite as well as being able to hang out by the main house outside on a very large table with friends. We had an amazing time celebrating our friends’s wedding. The only thing I would recommend is bringing your own sheets as it was difficult to wash all of them prior to leaving. I would certainly rent again with a large party of people.
Stayed 3 nights in Sep 2026
Verified review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Family Wedding

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 14 Oct, 2021
Thank you so much for the review. I've never heard anyone use the boat analogy but very accurate, hope you don't mind if I use that in the future! I am sorry about the need for towels and linens to be put in washer and run. With quick turnover, it is so helpful and we really appreciate the help we get from the renters. Lastly, I just wanted to be sure, while the renter did indicate the property is next to a wedding venue, that all future guests know that all venues on the island must stop music by 10 so that venders and guests can make the last boat. Noise is never an issue. Again thank you for your wonderful review.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely water front location. The two houses were perfect for our group of 13 (including 3 children). Well stocked kitchen. Enjoyed by all.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location. Beautiful spaces with a great layout for groups. Highly recommend and would stay again!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

Beautiful

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Loved it!

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

10/10 Excellent

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
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