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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076

Spacious Island Home, Walk to Beach, Private Baths!

Bedrooms 7
Half Baths1
Space 5,000 sq. ft.
Property type house
Minimum Stay 0 - 7 nights


About the property

7 bedrooms/5.5 baths (sleeps 13)

Smell the fresh air as you stroll on the magnificent sandy beaches of Long Island collecting sea glass or explore the rocky shoreline with your family and friends. This small, friendly island is just a 45 minute ferry ride from Portland, Maine and has approximately 200 year round residents. Our guests often comment about the beauty and tranquility of Long Island and how truly peaceful and relaxing a vacation here can be.

Chestnut Hill Cottage is a very spacious and charming 100 year old island home offering 7 bedrooms and 5.5 baths. Our maximum occupancy is 13 guests.

Just a short walk to the beach, this charming turn of the century home has been lovingly restored and updated to provide maximum comfort for those looking for a relaxing vacation retreat. We offer lots of amenities - 4 of our bedrooms have private baths - one of those with a private screened porch, two refrigerators in our large kitchen, laundry room, wet bar, three season room, dining room, double living room and a large screened porch on first floor. We also have a large open front porch where you can sip your coffee and listen to the rolling waves of South Beach as well as the lobster boats chugging along. Another large open side porch abuts the lawn where croquet can be played by day and marshmallows are roasted by night. Our second floor also has a common screened porch and additional sitting room.

The cozy island offers two stores (The Long Island Store and Boathouse Beverage and Variety) , a post office, gift shop, tennis courts, and library. Just about everything you need is within walking distance from this island gem, however, golf cart rentals are nearby - contact us for information. Your car can also be brought over with you but require arrangements in advance of your arrival - please contact Casco Bay Lines for additional information. Just be prepared to smile and wave as you pass your neighbors because that is the Long Island way!

Bedroom arrangements are as follows -

The Cove - Queen with private bath and screened porch

The Seaglass Room - Queen with private bath

The Garden Room - Queen with private bath

Cottage Square - Queen with private bath

The following rooms have a shared bath -

Beachside - Queen bed

Chestnut Grove - Two Twin beds

La Petite- one twin bed

Additional photos and information can be found on our Facebook page- Chestnut Hill Cottage-Long Island

Former Inn Keepers quarters are located in the back of the home with a separate entrance and may be occupied during the summer to assist with maintenance.

Day trips to historic Portland afford visitors the opportunity to walk around the famous Old Port where you will find fantastic restaurants, unique stores and other activities such as cinemas, The Portland Museum of Art, The Children's Museum, the Portland Observatory, the Longfellow House, the Victoria Mansion and many summer outdoor concerts. The Freeport shopping outlets are a 20 minute ride and is the location of Maine’s LL Bean store.

Keywords: large, island home, walk to beach, private baths, amenities, charming, family gatherings, peaceful, relaxing

More Details

Jane Babineau
Member since: 2011
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
February 10, 2018


Long Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 5000 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 13
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • Cancellation Policy per rental agreement
  • Away From It All
  • Family
  • Clothes Dryer
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking Off Street
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker ...
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Refrigerator ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Room
  • seating for 12 people
  • 5 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
  • 5.5
  • 7 Bedrooms, Sleeps 13
  • The Cove - 1 queen , w/ private bath and screened porch
    The Seaglass - 1 queen , with private bath
    The Garden - 1 queen , with private bath
    Cottage Square - 1 queen , with private bath
    Chestnut Grove - 2 twin/ single , with shared bath
    Beachside - 1 queen , with shared bath
    Bedroom 7 - 1 twin/ single , La Petite
  • Queen size Beds (5), Twin or Single Beds (2)One room with 2 twin beds
  • Books
  • CD Player
  • DVD Player
  • Games
  • Stereo
  • Television
  • VCR
  • Video Library
  • Balcony
  • Deck / Patio ...
  • Outdoor Grill
  • Tennis ...
  • wheelchair inaccessible
  • churches
  • library
  • marina
  • playground
  • recreation center
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • shelling
  • shopping
  • sight seeing
  • walking
Sports & Adventure Activities:
  • basketball court
  • cross country skiing
  • cycling
  • deepsea fishing
  • fishing
  • kayaking
  • mountain biking
  • pier fishing
  • sailing
  • surf fishing
  • surfing
  • swimming
  • tennis
Four bedrooms have private baths, large three season room on first floor, open front porch, large screened side porch, second floor screened porch, two refrigerators in kitchen, wet bar, double living room, dining room, short walk to beautiful beach, sand chairs, outdoor firepit


Exceptional! 5/5 -
(10 traveler reviews)

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Spacious Island Home, Walk to Beach, Private Baths!
average rating of 5.0 based on 10 reviews
Alexandria, VA

Birthday Bash!

  • 5 of 5

We stayed at Chestnut Hill this August and LOVED it! We had anything from 7 to 12 people over night, fed up to 20 at dinner and never felt crowed. The property is ideal for anything from a quiet afternoon with a book to a raucous gathering of good friends. Beach is beautiful, rooms are great! Would definitely go back.

  • Submitted: Sep 6, 2014
  • Stayed: August 2014
  • Source: VRBO, from HomeAway
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0 0

Massachusetts family

  • 5 of 5

This was our second year of a three generation family vacation at Chestnut Hill and again it was a wonderful relaxing time. Everything we needed was there, clean and in working condition. There is lots for kids to do, beaches, bikes, tennis, playground and library and downtown Portland is a 20 minute ferry ride away for more off-island family activities. We have already booked our 2015 vacation at Chestnut Hill.

  • Submitted: Jul 19, 2014
  • Stayed: July 2014
  • Source: VRBO, from HomeAway
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1 0

Big family

  • 5 of 5

Great spot for a family reunion, with a very well-equipped and spacious kitchen. The bedrooms (most with up-to date private bath) are attractive and spacious. Good beaches are close by within easy walking distance, and the whole island is easily accessible by bike.

  • Submitted: Aug 23, 2012
  • Stayed: July 2012
  • Source: VRBO, from HomeAway
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1 0
Winthrop Maine


  • 5 of 5

We celebrated our 25th wedding anniversary at Chestnut for a long weekend in June. Our entire family came out and were stunned by the beautiful decor, cleanliness, and spaciousness. We all agreed that we should have rented it for the entire week because the weekend wasn't long enough!

The Babineau's were gracious hosts and tended to our every need.

We will be back!!

  • Submitted: Jul 19, 2012
  • Stayed: June 2012
  • Source: VRBO, from HomeAway
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1 0
Cumberland, RI

Weekend of Relaxation and Luxury

  • 5 of 5

I recently stayed at the Chestnut Hill Cottage in early June for a "girls getaway." The property and amenities were absolutely beautiful, well taken care of, and very spacious. I could have stayed in the kitchen the entire time I was there! No stone was left unturned, and the owners of the cottage covered everything from linens to towels to a Keurig machine and full dishware! This is a perfect getaway for a family, groups of friends, or even a staff retreat. I am truly looking forward to going back again! The island itself was beautiful, charming, and the perfect setting for a quiet, relaxing vacation away from home.

  • Submitted: Jul 16, 2012
  • Stayed: May 2012
  • Source: VRBO, from HomeAway
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2 0
Templeton, MA

Summer 2012

  • 5 of 5

Just gone done staying at chestnut hill with my wife, my parents, part of my wife's family, my brother and his family, and my aunt and uncle. We had a full house, but it never felt crowded. This is definitely a great spot. It's only a few minutes walk to the beach, and even shorter walk to the library/basketball courts/tennis court. We rented a golf cart to get around, but you don't need to if you don't mind a little walking. The rooms are all beautiful and comfortable, and bigger than they look in the pictures. Many nooks to hide out in and read a book, and many different porches. I think long island Is the best place to vacation ive ever been to, and this may be the best place on long island. I very highly recommend it!

  • Submitted: Jul 15, 2012
  • Stayed: July 2012
  • Source: VRBO, from HomeAway
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3 0


Long Island South Beach
Car: recommended

Shopping in Portland's Old Port, excellent restaurants in Portland area, Freeport shopping outlets including LL Bean




Additional information about rental rates

Refundable damage deposit $250

Cancellations are per our rental agreement. We offer weekly, seasonal rentals but can be more flexible in early Summer and Fall. Please contact us for additional information.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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