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Cottage from the bottom of the yard in the woods

Overview
Amenities
Policies
Location
Host

9.8

Exceptional

5 bedrooms1+ bathroomSleeps 8204 sq m

Popular amenities

Washer

Pet-friendly

Outdoor space

Kitchen

Dryer

Check-in time

4:00 PM

Check-out time

11:00 AM

Explore the area

Little Diamond Island, ME

Sand Beach4 min walk
Casco Bay Lines Ferry Terminal21 min drive
State Theatre22 min drive
Portland, ME (PWM-Portland Intl. Jetport)45 min drive

Most relevant reviews

10/10 Excellent

Truly special property and cottage. Very private at the top of the hill. Plenty of room for seven adults and two dogs, a...

Dan O.

Aug 9, 2021

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

Spaces

Deck or patio

Porch or lanai

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

Property manager

David Woodbury

Languages

English

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Outdoor space

Kitchen

Washer

Dryer

Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 21

Check out before 11:00 AM

Children

Adults only

Antiques in home, but careful children welcome

Events

No events allowed

Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)

One small behaved dog >30 lbs with prior approval

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. Notable landmarks in the area include State Theatre and Portland Head Light, and travellers wishing to experience a bit of culture can try Thompson's Point. Maine Sports Hall of Fame and Maine Narrow Gauge Railroad Company and Museum 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/biking trails nearby.

Little Diamond Island, ME

What's nearby

Sand Beach - 4 min walk
Casco Bay Lines Ferry Terminal - 21 min drive
Cross Insurance Arena - 22 min drive
State Theatre - 22 min drive
Thompson's Point - 26 min drive

Getting around

Portland Transportation Center - 38 min drive
Portland, ME (PWM-Portland Intl. Jetport) - 45 min drive

Restaurants

‪Lolita-Munjoy Hill - ‬22 min drive
‪Brickyard Hollow Brewing Company - ‬22 min drive
‪Twelve - ‬23 min drive
‪Evelyn's Tavern - ‬27 min drive
‪Saltwater Grille - ‬27 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.

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 Fort Gorges are also within 5 minutes.

9.8

Exceptional

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

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Dan O.

9 Aug 2021

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

10/10 Excellent

Betsy K.

1 Aug 2021

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

10/10 Excellent

Evelyn W., Easthampton, MA, USA

24 July 2021

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

10/10 Excellent

Bill G.

2 Sept 2020

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

10/10 Excellent

Bill G.

9 Oct 2019

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.

10/10 Excellent

Bill G.

28 Aug 2018

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

8/10 Good

Joseph P.

13 Aug 2018

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

10/10 Excellent

Scott U., New Orleans

28 July 2018

Decompression Central

Great place to relax, read and get away from modern life for awhile

Stayed 7 nights in Jul 2018

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Kenia G.

20 Sept 2017

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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Elizabeth S.

13 Sept 2017

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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Melissa G.

22 Aug 2017

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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Everett I.

27 July 2017

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.

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Peg E., Gulfport

26 July 2017

Lovely home

Lovely home and property. My only suggestion is to have larger or second garbage bin.

Stayed 9 nights in Jul 2017

This review was submitted before 2018 and has not been verified.

8/10 Good

Jodie F., New Hampshire

22 July 2014

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.

About the host

Hosted by 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.

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.