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Historic Island Cottage, 5BR

Photo gallery for Historic Island Cottage, 5BR

Cottage in early autumn
Approaching the Cottage
Cottage from the side yard
Cottage from the bottom of the yard in the woods
Property grounds

Reviews

9.8 out of 10
Exceptional
5 bedrooms1+ bathroomSleeps 8204.4 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Outdoor space

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

About this property

Historic Island Cottage, 5BR

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, 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

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Adults only
Antiques in home, but careful children welcome
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)
One small behaved dog >30 lbs with prior approval
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Smoking

Smoking is not permitted
* Approved small dog not allowed on furniture, not allowed in house when wet or sandy from beach, and must be kept from scratching at screen doors.

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 not indicated whether there is a smoke detector on the property

About the area

Portland

Located in Portland, this cottage is near the beach. N.W. Barrett Gallery and Maine Jewish Museum are cultural highlights, and some of the area's attractions include Maine Narrow Gauge Railroad and Portland Observatory. Bayside Bowl and Center for Cultural Exchange are also worth visiting. Discover the area's water adventures with kayaking, power boating and fishing nearby, or enjoy the great outdoors with hiking/biking trails.
View more Cottages in PortlandOpens in a new window
Map
Little Diamond Island, ME

What's nearby

  • Little Diamond Island - 1 min walk - 0.0 km
  • Sand Beach - 6 min walk - 0.6 km
  • Fort Gorges - 6 min walk - 0.6 km
  • Casco Bay Lines Ferry Terminal - 21 min drive - 4.1 km
  • Fore Street Gallery - 22 min drive - 4.4 km

Getting around

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

Restaurants

  • ‪Second Rodeo Coffee - ‬28 min drive
  • ‪Twelve - ‬23 min drive
  • ‪North43Bistro - ‬27 min drive
  • ‪Brickyard Hollow Brewing Company - ‬22 min drive
  • ‪Double Great Coffee - ‬24 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 4 Apr 2026, prices found for a 1-night stay for 2 adults at Historic Island Cottage, 5BR on 5 Apr 2026 start from AU$528, 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

Verified

10/10 Excellent

Dan O.

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

10/10 Excellent

Betsy K.

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

10/10 Excellent

Evelyn W.

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

10/10 Excellent

Bill G.

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

10/10 Excellent

Bill G.

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

10/10 Excellent

Bill G.

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

8/10 Good

Joseph P.

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

10/10 Excellent

Scott U.

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

Kenia G.

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

Elizabeth S.

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

Melissa G.

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

Everett I.

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

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
Archival

8/10 Good

Jodie F.

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! :-)

About the host

Hosted by David Woodbury

Host profile image
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.

Why they chose this property

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 property 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.

Languages:

English
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