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

5 bedrooms2+ bathroomsSleeps 14223 sq m

Popular amenities

Kitchen

Barbecue grill

Washer

Dryer

Air conditioning

Outdoor space

Check out the area

Peaks Island, ME

Casco Bay Lines Ferry Terminal26 min drive
Cross Insurance Arena28 min drive
State Theatre28 min drive
Portland, ME (PWM-Portland Intl. Jetport)42 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

About this property

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.

Property manager

Greg Carter

Amenities

Kitchen

Washer

Dryer

Air conditioning

Outdoor space

Ocean view

Welcome to our unique Maine seaside island cottage rental Selkies Rest: Portland

Hot tub

Kitchen

Washer

Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

The house(s) and property cannot be used for any type of function or gathering beyond the people staying at the property.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Peaks Island

Located in Peaks Island, this cottage is in the city centre and on the beach. Thompson's Point and Umbrella Cover Museum are cultural highlights, and some of the area's attractions include Maine Sports Hall of Fame and Maine Narrow Gauge Railroad Company and Museum. Travelling with kids? Consider Portland Observatory, or check out an event or a game at Merrill Auditorium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Peaks Island, ME

What's nearby

Sand Beach - 6 min drive
Casco Bay Lines Ferry Terminal - 26 min drive
Cross Insurance Arena - 28 min drive
State Theatre - 28 min drive
Thompson's Point - 32 min drive

Getting around

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

Restaurants

Luke's Lobster Portland Pier - 27 min drive
Lolita-Munjoy Hill - 28 min drive
Brickyard Hollow Brewing Company - 27 min drive
The Porthole - 27 min drive
Twelve - 28 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.

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 Casco Bay Lines Ferry Terminal are also within 3 miles (5 km).

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

paul m.

17 Oct 2023

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

10/10 Excellent

Liz and Joe G.

9 Sept 2023

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

10/10 Excellent

Martha C.

1 Sept 2023

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

Family Wedding

Everyone loved the location! House was perfect!

Stayed 7 nights in Aug 2023

10/10 Excellent

Katie H.

19 Sept 2022

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

10/10 Excellent

Nancy F.

12 Sept 2022

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

Beautiful

Everything at Cindy’s place was absolutely perfect!

Stayed 3 nights in Sep 2022

About the host

Hosted by Greg Carter

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.

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