Entire home

Historic Island Cottage, 5BR

Photo gallery for Historic Island Cottage, 5BR

A red house with a porch and a chimney.
A room with wicker furniture and red cushions, a wooden coffee table with magazines, and a view of trees through large windows.
A snow-covered landscape with a red house surrounded by trees.
A dining room with a table set for four, surrounded by chairs, with a window and curtains on one side.
A room with a piano, a door, a chair, and a table with a lamp.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Discover nearby landmarks
    Near Casco Bay

Popular amenities

  • Patio
  • Dog-friendly
  • Refrigerator
  • Internet
  • Washing machine
  • Bathtub

Explore the area

View map
Little Diamond Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Little Diamond Island
    ‪1 min walk‬
  • Place, Sand Beach
    ‪8 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪36 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Double Bed

Bedroom 5

1 Single Bed

1 bathroom, 1 half bathroom

Bathroom 1

Bathtub · Toilet

Bathroom 2

Toilet

Outdoor shower

Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Separate dining area
Garden

Add dates for prices

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About the area

Portland

Located in Portland, this cottage is near the beach. State Theatre and Thompson's Point are cultural highlights, and travellers looking to shop may want to visit Maine Mall. Maine Sports Hall of Fame and Maine Narrow Gauge Railroad are also worth visiting. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
View more Cottages in PortlandOpens in a new window
Map
Little Diamond Island, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Little Diamond Island - 1 min walk - 0.0 km
  • Sand Beach - 8 min walk - 0.7 km
  • Fort Gorges - 8 min walk - 0.7 km
  • Maine Sports Hall of Fame - 21 min drive - 4.1 km

Getting around

  • Freeport Station - 40 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 49 min drive

Restaurants

  • ‪7-Eleven - ‬23 min drive
  • ‪Brickyard Hollow Brewing Company - ‬22 min drive
  • ‪Duoro - ‬23 min drive
  • ‪Twelve - ‬23 min drive
  • ‪Second Rodeo Coffee - ‬28 min drive

Frequently asked questions

Is Historic Island Cottage, 5BR pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

How much does it cost to stay at Historic Island Cottage, 5BR?

As of 5 Nov 2026, prices found for a 1-night stay for 2 adults at Historic Island Cottage, 5BR on 1 Jan 2027 start from AU$8,513, 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.

What time is check-in at Historic Island Cottage, 5BR?

Check-in begins at 4:00 PM.

What time is check-out at Historic Island Cottage, 5BR?

Checkout is at 11:00 AM.

Where is Historic Island Cottage, 5BR located?

Situated by the ocean, this cottage is steps away from Casco Bay and Little Diamond Island. Sand Beach and Casco Bay Lines Ferry Terminal are also within 3 miles (5 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. 12 out of 14 reviews
Rating 8 - Good. 2 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Archival

10/10 Excellent

Lovely home

Lovely home and property. My only suggestion is to have larger or second garbage bin.
Stayed 9 nights in Jul 2017
Verified review

10/10 Excellent

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

Island Bliss - Great way to unplug

Truly special property and cottage. Very private at the top of the hill. Plenty of room for seven adults and two dogs, and we all enjoyed the large yard and spacious accommodations. Historical 1885 cottage with all the antiquities, but also the creature comforts. First time in long time that a vacation truly allowed us all to unplug, enjoy nature, the simple life, and each other's company. Easy access to quiet beaches, walks to adjoining island, short ferries into Portland for eateries/shopping/sightseeing. We live only 20 minutes away, but Casco Bay and Portland offer the best vacationing we know of.... It's true....Maine, the way life should be.
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

Beautiful week on Little Diamond

Absolutely lovely, thank you! The house has everything we needed, especially well-equipped kitchen, outdoor space, gorgeous little island.
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

Beautiful stay on Little Diamond

My family and I (all adults) spent a week at the Woodbury house on Little Diamond Island. With David’s instructions we easily made it to the island and ordered our food for the week from Portland. We spent lots of time with our dog at the beach, cooked dinners, and enjoyed the beautiful house. Would love to come back!
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

This was our fourth year in this cottage. We love it and plan to be back again next year.

Lots of room, well equipped, very clean, private location, beaches, views.
Stayed 14 nights in Aug 2020
Verified review

10/10 Excellent

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

Wonderful Cottage Experience

Our stay at the Woodbury Cottage was excellent! From nicely furnished rooms to large kitchen with all the tools to sounds of boats all around us, we thoroughly enjoyed our return trip to the cottage. Looking forward to next year already.
Verified review

10/10 Excellent

Beautiful historic cottage. Quiet friendly island. Convenient to Portland yet a world away.

We love and appreciate the fresh touches and improvements that have gone into the cottage and grounds. It is the right size for our family. Friendly people on the island. The short ferry ride to Portland is fun and convenient. The walk to Great Diamond during low tide provides exercise and different views. The cottage and island are very conducive to relaxing and leaving your cares behind.
Stayed 14 nights in Aug 2018
Verified review

8/10 Good

Great location on beautiful little diamond island

The house accommodated 9 of us without trouble and had everything we needed for a great vacation. The island is really beautiful. The home is historic and has some great outdoor and porch space. There are a lot of antiques (including the furniture) which did make us nervous with younger children. Overall, we had a wonderful stay. David was very responsive to any questions that we had and so are the other islanders.
Stayed 7 nights in Aug 2018
Verified review

10/10 Excellent

Decompression Central

Great place to relax, read and get away from modern life for awhile
Stayed 7 nights in Jul 2018
Archival

10/10 Excellent

Lovely and Interesting

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 !
Stayed 4 nights in Sep 2017
Archival

10/10 Excellent

Beautiful site and charming house.

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.
Stayed 9 nights in Aug 2017
Archival

10/10 Excellent

A Step Back in Time

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
Stayed 12 nights in Aug 2017
Archival

10/10 Excellent

Exactly what we wanted!

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.
Archival

8/10 Good

Treasured memories

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 distance...it is cumbersome for lugging supplies, etc.
Response from VrboOwner on 17 Mar 2020
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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