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

Historic Island Cottage, 5BR

Bedrooms 5
Half Baths1
Space 2,200 sq ft
Property type cottage
Minimum Stay 7 nights


About the property

Cottage, 5 Bedrooms + Sunroom, 1.5 Baths, (Sleeps 7 - 9)

Spacious Victorian cottage built in 1885 by celebrated architect John Calvin Stevens, located on Little Diamond Island, a 15 minute ferry ride from the vibrant city of Portland, Maine, but worlds away from the hustle and bustle of everyday life.

Our family owned home has five bedrooms with full/double beds, plus a sunporch which can become an extra bedroom. The house is supplied with linens and cooking utensils, washer/dryer, a picnic table and an outdoor shower that is a delightful summer experience!

The house is situated next to conservation woods, on an acre lot, with privacy that is wonderful for quality family time. It offers a wrap-around front porch with hammock, a screened-in back porch, ample yard space for croquet or bocce, and a tree swing for kids of all ages. Choice island beaches are only minutes away for swimming and beach combing.

With no cars on the island, the pace is peaceful and relaxing. At low tide, you can walk across the sandbar to Great Diamond Island, stop for ice cream or a few staples at the store, and ride the ferry back to Little Diamond for free. Inter-island ferry is free of charge for exploring down the bay. The short ferry ride into town provides easy access to Portland restaurants, museums, shopping, and a rich array of other off-island activities in Southern Maine.

Keywords: island cottage, house, wrap around porch, yard, tree swing, beach access

More Details

David Woodbury
Member since: 2011
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
April 20, 2018

About David Woodbury

Our family has owned this property for 50+ yrs. My Great Aunt first signed the guestbook in 1914, and multiple generations have enjoyed it since my Grandparents' purchase in the late 1950s. Many reunions and celebrations have been held here, creating wonderful memories for our family and friends. It has been 'home' for people living overseas or moving frequently and is dear to us all.

David Woodbury purchased this cottage in 1959

Why David Woodbury chose Little Diamond Island Landing

My Grandmother and Great Aunt knew the previous owners since childhood and my Father and Uncle came here often to visit. There was a strong attachment to this house before it became 'ours.'

What makes this cottage unique

There is nothing like an island with no cars, hearing the bell buoys, listening to the summer night. The community includes many families who have been on the island for generations as well as newcomers to the joys of island living.


Little Diamond Island Landing Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 2200 sq ft
House Rules:
  • Check-in: 4:30 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 9
  • Children welcome ...
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only
  • * Approved pets are not allowed on furniture, or in house when wet or sandy from the beach, and must be kept from scratching at screen doors.
  • Clothes Dryer
  • Internet
  • Linens Provided
  • Living Room
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining
  • Dining Room
  • seating for 8 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 2 - toilet
    Bathroom 1 - toilet , tub
    Outdoor shower - outdoor shower
  • 1.5
  • 5 Bedrooms, Sleeps 9
  • Bedroom 1 - 1 double
    Bedroom 2 - 1 double
    Bedroom 3 - 1 queen
    Bedroom 4 - 1 double
    Bedroom 5 - 1 double
    Upstairs Sunroom - 1 baby crib
  • Queen size Beds (1), Double Beds (4), Baby Cribs (1)
  • Deck / Patio
  • Lawn / Garden
  • cinemas
  • live theater
  • museums
  • restaurants
Leisure Activities:
  • boating
  • shelling
  • shopping
  • sight seeing
  • walking
Sports & Adventure Activities:
  • fishing
  • hiking
  • kayaking
  • swimming


Wonderful! 4.8/5 -
(6 traveler reviews)

83% Complete
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Historic Island Cottage, 5BR
average rating of 4.8333335 based on 6 reviews

Lovely and Interesting

  • 5 of 5

The Historic Cottage is very spacious and comfortable. It has a big yard and the people there are lovely and friendly. The house has old things that is interesting to see... I really did enjoy my stay with my family !

  • Submitted: Sep 5, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Beautiful site and charming house.

  • 5 of 5

Near a beautiful beach, 15 minutes from Portland by ferry, and very nice people. Gorgeous gardens. Small island - - runners needed to go around several times to get a good few miles in! No TV, Radio. Kids could use Netflix to watch programs on computers at the end once or twice. PERFECT weather. Bring a book or two, a deck of cards, and some good walking shoes. Amazing birds. Saw a mink, turkeys, other wildlife. VERY quiet at night. Slept like a log. Baked and cooked like mad. It was just right. Owner very nice.

  • Submitted: Aug 29, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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A Step Back in Time

  • 5 of 5

This charming cottage is spacious and well appointed. For those who appreciate historical architecture, your stay is like a step back in time to days of romance and relaxation.

Melissa and Bill

  • Submitted: Aug 17, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Exactly what we wanted!

  • 5 of 5

We have a cottage on Little Diamond Island already. We needed a second place to house my family for a week. The Woodbury cottage fit our needs to a T. We were lucky to get it. The cottage was charming, well-kept, well-appointed, and well-stocked. The five bedrooms were a real plus. Everyone who stayed there loved the place. David has done a lot of work on the cottage recently, and it shows.

  • Submitted: Jul 27, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Lovely home

  • 5 of 5

Lovely home and property.

My only suggestion is to have larger or second garbage bin.

  • Submitted: Jul 25, 2017
  • Stayed: July 2017
  • Source: HomeAway
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New Hampshire

Treasured memories

  • 4 of 5

This authentic historic home is a perfect place for family and friends to gather. It offers one of the most private cottages on the island! The cottage takes you back in time. The one missing element is a golf cart. Although everything is within walking is cumbersome for lugging supplies, etc.

  • Submitted: Jul 19, 2014
  • Stayed: July 2014
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for your comments, Jodie! We have loved having you at our home for the past 3 summers! We love the walking environment on the island and want to retain that as much as possible. The hand carts are better than the wheelbarrows my father used to use! :-)
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Nearest Airport
6 Miles
Portland International Jetport (PWM)
Nearest Ferry
400 Metres
Casco Bay Lines
Nearest Train
5 Miles
Amtrak (Downeaster)
Nearest Beach
400 Metres
Little Diamond Island Beaches


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Property Damage Protection $59
Tax Rate 9.0%

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 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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