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The Woodbury Cottage: An Oceanfront Maine Island Escape

Bedrooms 3
Property type cottage
Minimum Stay 2 - 6 nights


About the property

The Woodbury Cottage is the perfect place to unplug, unwind and relax! Located on Great Diamond Island, in Casco Bay off Portland, Maine, it is a quick ferry ride down the bay. The cottage can accommodate 8 guests between three bedrooms and one bathroom. Guests can enjoy complete quiet relaxation and solitude at the cottage which is located on a private corner of the island or head out and explore what the island has to offer, which includes walking trails, a tennis court, a basketball court, General Store and Diamond's Edge--a bar and restaurant located on the opposite side of the island.

Property Manager
Jason O'Brien
Member since: 2015
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
September 19, 2018


Great Diamond Island Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
House Rules:
  • Check-in: 3:00 PM / Check-out: 10:00 AM
  • Max. occupancy: 8
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Ocean View
  • Oceanfront
  • Water View
  • Waterfront
  • Away From It All
  • Family
  • Clothes Dryer ...
  • Fireplace ...
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Towels Provided
  • Coffee Maker ...
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower
    Bathroom 2 - toilet , shower
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 double
    Bedroom 2 - 1 double
    Bedroom 3 - 3 twin/ single , 1 bunk bed
  • Books
  • Games
  • Stereo ...
  • Balcony ...
  • Deck / Patio
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • playground
  • restaurants
Leisure Activities:
  • walking
Sports & Adventure Activities:
  • fishing
  • tennis
Owner has contacts for a private chef, private yoga instructor and massage therapist that can travel to the island. All is based on availability and not guaranteed.


Exceptional! 5/5 -
(16 traveler reviews)

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The Woodbury Cottage: An Oceanfront Maine Island Escape
average rating of 5.0 based on 16 reviews

Overall, this property is well maintained and perfect for an escape from the city.

  • 5 of 5

Owner was great to work with. They don’t allow cars on the island, so you need to either walk or use the golf cart (provided). Being on the ferry schedule was a challenge, but very easy to use and affordable. Neighbors are sweet, they invited us to watch an outdoor movie with them. The property is right on the water with a wonderful wrap around porch you can enjoy a cup of coffee or a glass of wine on. We want to come back and bring our boys for a getaway from all the noise of the city!

  • Submitted: Sep 18, 2018
  • Stayed: September 2018
  • Source: VRBO, from HomeAway
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Amherst, MA

Beautiful island, beautiful house

  • 5 of 5

The house was very clean, organized, well decorated and cute. Beds were very comfortable. The porch is awesome with an unparalleled view of the boats, the osprey and Peaks Island. We played tennis and used the relaxing hammocks. The kitchen was well stocked and we had all the cookware we needed. The island is beautiful and you can walk to Little Diamond Island at low tide. Our teenagers loved jumping off the ferry dock. It was truly a perfect vacation.

  • Submitted: Aug 19, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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Beautiful, quaint New England Island retreat.

  • 5 of 5

Comfortable and fully stocked. The island is lovely and the views from the cottage are beautiful. We liked everything about the property.

The comfort of the beds was outstanding. We rent homes all over the world and I have not had a good night sleep. However, thus cottage was different. We felt cozy, comfortable, pillows were amazing. I slept 9 hours every night. This never happens. I can't wait to go back.

  • Submitted: Sep 4, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Boston, MA


  • 5 of 5

Beautiful cottage, gorgeous views. Couldn't have asked for a better place to relax for the week.

  • Submitted: Aug 31, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Relaxing, comfortable, beautiful location!

  • 5 of 5

We very much enjoyed our week on Great Diamond. The ferry was convienient and we had a great mix of relaxation on the island, time in Portland, and a day in Acadia. Great property! Highly recommend.

  • Submitted: Aug 5, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Dreamy New England Island Retreat

  • 5 of 5

The Woodbury Cottage couldn't have been more idyllic and relaxing. Visiting Maine during peak fall foliage has been a bucket list item for us, and I decided to surprise my husband with this mini vaca to celebrate our 15-year wedding anniversary. So glad I did! This home is a true gem and a must-do if you're visiting Portland. It's on an island (let me say that's on an island!), oozing with New England charm, impeccably decorated, and just a short ferry ride to the mainland.

During our stay, the island was extremely quiet and peaceful since most things shut down by Columbus Day, but we welcomed that. We love the crisp, cool weather, and welcomed the chance to unplug. Although relaxed, this stay most definitely packed in the adventure. Everything was a first for us...first stay on an island, first ferry ride, first water taxi, first lobster boil...and we'll never forget it.

Every convenience had been thought of, and Jason (owner/manager) was so accommodating and helpful! He took the time to provide recommendations to try during our stay, including fresh lobster from a local fisherman and having groceries delivered by ferry. All necessary amenities were provided along with the basic pantry items for cooking.

When we return, we plan to go just before Columbus Day to take advantage of more shops and activities in Portland, but we were thrilled with our stay. The locals on Great Diamond Island were extremely kind and welcoming, and we just can't wait to go back.

Best. Trip. Ever.

  • Submitted: Mar 31, 2017
  • Stayed: October 2016
  • Source: HomeAway
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $100
Refundable damage deposit $500

Rates are subject to change until reservation is confirmed.

Manager'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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