See all properties
Entire home

The Woodbury Cottage: An Oceanfront Maine Island Escape

Photo gallery for The Woodbury Cottage: An Oceanfront Maine Island Escape

Exterior
Beach
Beach
Miscellaneous
Property grounds

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Kitchen
  • Barbecue grill
  • Air conditioning

Explore the area

Map
Portland, ME
  • Sand Beach
    ‪5 min drive‬
  • Casco Bay Lines Ferry Terminal
    ‪26 min drive‬
  • East End Beach
    ‪28 min drive‬
  • Portland, ME (PWM-Portland Intl. Jetport)
    ‪34 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed and 1 Single Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

The Woodbury Cottage: An Oceanfront Maine Island Escape

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

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Exterior

Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants.

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
9.6 out of 10, (5 reviews)
Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants.

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted
Security cameras must remain plugged in at all time.
Departure checklist must be followed to receive full refund of security deposit.
Guests should not go through owner's property.

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Portland

Located in Portland, this cottage is on the waterfront. State Theatre and Thompson's Point are cultural highlights, and travellers looking to shop may want to visit Maine Mall. Maine Narrow Gauge Railroad Company and Museum and Portland Observatory are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
Map
Portland, ME

What's nearby

  • Sand Beach - 5 min drive - 2.2 km
  • Casco Bay Lines Ferry Terminal - 26 min drive - 5.9 km
  • State Theatre - 27 min drive - 7.0 km
  • East End Beach - 28 min drive - 7.3 km
  • Thompson's Point - 30 min drive - 10.2 km

Getting around

  • Portland Transportation Center - 35 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 50 min drive

Restaurants

  • ‪Brickyard Hollow Brewing Company - ‬26 min drive
  • ‪North43Bistro - ‬37 min drive
  • ‪Twelve - ‬27 min drive
  • ‪Speckled Ax - ‬31 min drive
  • ‪Duckfat - ‬31 min drive

Frequently asked questions

Is The Woodbury Cottage: An Oceanfront Maine Island Escape pet-friendly?

No, pets are not allowed at this property.

What time is check-in at The Woodbury Cottage: An Oceanfront Maine Island Escape?

Check-in begins at 4:00 PM.

What time is check-out at The Woodbury Cottage: An Oceanfront Maine Island Escape?

Checkout is at 10:00 AM.

Where is The Woodbury Cottage: An Oceanfront Maine Island Escape located?

Situated on the waterfront, this cottage is within a 15-minute walk of Casco Bay and Little Diamond Island. Sand Beach and Fort Gorges are also within 2 miles (3 km).

Reviews

10

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. 22 out of 22 reviews
Rating 8 - Good. 0 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

10/10 Excellent

Melinda Dore A.

The best of everything

This was the perfect getaway for two families to relax and unwind with plenty of room for everyone...the kids commandeered the large upstairs room and couldn't have been happier. Our families took advantage of shell collecting, swimming, long walks, the beach on Long Island, and the restaurants in Portland, all just an easy walk or ferry ride away. Living car free made the vacation extra special and we look forward to returning. How lucky for us that the thoughtful and attentive owners are willing to share the Woodbury Cottage through VRBO!
Stayed 7 nights in Aug 2016

10/10 Excellent

Samuel H.

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

Beautiful and peaceful!

We loved our stay - the property is beautiful and peaceful. The view is paradise, and we could sit in the huge back porch all day watching the boats from up on the hill. The rock beach at the bottom of the hill is great for a dip or hunting sea glass. Eric and Jason were great hosts all around. The island is very quiet, with two restaurants, including one called Crown Jewel, which has the best food I’ve had in a long time - I only wish we could have gotten a reservation more than twice! Truly a great way to spend a couple weeks!!
Stayed 14 nights in Jul 2023

10/10 Excellent

Jenny B.

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

Maine Paradise!

Jason was very organized, detailed, and kind in all of his dealings with us! This cottage was absolutely magical with how beautiful inside and outside that it was! The island was fun to explore and everyone we met was very friendly! Only a short ferry ride to Portland…but we missed the cottage so much when we left that we only spent a couple hours in the city and came back haha!
Stayed 4 nights in Jun 2022

10/10 Excellent

Laura F.

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

Paradise in Maine

Jason is an excellent host. The cottage was perfect. We couldn’t have asked for a better vacation!
Stayed 21 nights in Jul 2021

10/10 Excellent

Alethea O., Amherst, MA

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

Another great week

We came back to this property for another 8 nights after enjoying it so much last summer. The rental was perfect again. The setting is so relaxing and we love the quiet island, with the ability to go into Portland so easily. Jason has thought of everything a guest could need. We love GDI and hope to return next year.
Stayed 8 nights in Jul 2019

10/10 Excellent

Nathan N.

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

Maine retreat

We had a lovely three-night stay at The Woodbury. Communication with Jason, the manager, was excellent, and everything was as advertised. Would absolutely recommend, and hope to come back soon.
Stayed 3 nights in Jun 2019

10/10 Excellent

Marcella B.

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

Perfect Getaway

We just had a most perfect getaway for my husband’s 60th birthday! My husband, daughters and 2 year old grandson spent a long weekend together at Woodbury Cottage. The cottage was the most well-appointed rentals I have ever been to. Every detail was attended to. The bedsheets were high quality & soft. The decor was super-cute. There was a beer cooler on the porch, 3 separate tables to gather around & eat at, plenty of utensils, dishes, pots/pans...there was even a huge basket of “supplies” in the bathroom for use by the renters. All-in-all, we had a beautiful time enjoying the view, the island and each other. Thank you for sharing your lovely cottage, Jason.
Stayed 3 nights in Jun 2019

10/10 Excellent

Catherine B.

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

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!
Stayed 2 nights in Sep 2018

10/10 Excellent

Alethea O., Amherst, MA

Beautiful island, beautiful house

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.
Stayed 7 nights in Aug 2018
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Terry R.

Beautiful, quaint New England Island retreat.

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.
Stayed 3 nights in Sep 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Katherine B., Boston, MA

Perfection

Beautiful cottage, gorgeous views. Couldn't have asked for a better place to relax for the week.
Stayed 7 nights in Aug 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Susan G.

Relaxing, comfortable, beautiful location!

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.
Stayed 7 nights in Jul 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Crystal A.

Dreamy New England Island Retreat

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

10/10 Excellent

Chrissy G.

Wonderful cottage with amazing views

We just returned from a long Labor Day Weekend on Great Diamond Island - what a treat! This cottage is absolutely adorable and fully stocked with everything you can imagine - and so nice not to have to bring linens. Jason, the owner, is an incredible host who made us feel right at home with a lovely welcome basket filled with all kinds of treats. The view from the front porch is stunning and we so enjoyed watching all the activity on the water. We brought three teenagers who spent their days swimming, and playing basketball and tennis...they also took the ferry to Portland for one afternoon. We took Jason's advice and had lobsters delivered right to our door for our last evening on the Island. We would strongly recommend this cottage and hope to return next year! Truly a very special place.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Amazing cottage

I had such a good time at the Woodbury Cottage. It's a beautiful house, and was well equipped with everything we needed. I'd definitely recommend it to anyone!
Stayed 3 nights in Aug 2016
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Paula S.

A true 'Maine style Cottage'

Spent a week with a couple from the west coast visiting Maine for the first time. They occupied the upstairs suite as we referred to it , while my husband and I took the downstairs. Another couple visiting two nights occupied the third bedroom downstairs. Just note these rooms are aimed at the ' light traveler '. This is a true Maine style cottage. Very impressive homeowner and punctual in responding. Thankfully there was no TV so we watched the boat traffic all day. As two couples traveling from the DC and San Francisco areas, this was a real treat ! We parked our car for the week and rented a locally built 'Foggcraft' in Portland. Pack accordingly as there is no washer or dryer. Kitchen well stocked with spices , oils and wonderful lobster dinner accessories. Love the red plastic trays. Nice white fluffy towels . The " things I forgot " Basket came in handy as I forgot a lot. Great walking Island. So glad we didn't get kicked off and look forward to returning next year! It was perfect. Thank you Jason !
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Meagan Z.

idyllic island get away spot

We had a wonderful stay at the Woodbury cottage this summer. The property is peaceful and beautiful, with a lovely porch overlooking the water, where we had dinner each night watching the boats go by. I've rented several different homes in Casco Bay and the Woodbury Cottage had the best amenities by far! The kitchen has all the tools you need to cook and entertain, along with a fully stocked pantry of cooking essentials (which is very helpful when you're bringing a week's worth of groceries out on the ferry boat - no need to bring a bottle of olive oil, ketchup, mustard etc). Each corner of the house was comfy + cozy, showers were great with lovely towels and linens. The owners were gracious, quick and easy to communicate with - a great experience over all.
Stayed 5 nights in Jul 2016
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Gorgeous Getaway

Not only is this house and property charming, clean and neat, it is really the thought, effort and hospitality that go into guests’ stays that make this property truly exceptional. We rented last year and had an amazing time. There was a gift basket waiting for us with Maine specific products. The house was immaculately clean upon our arrival as well. There was also a basket of travel items in the bathroom in case we had forgot to pack anything. We were planning on returning this year anyways, but the owners reached out to us to let us know that the same week we rented last year was still available this year and wanted to know if they should hold it for us. The personal invitation back was just very special and much appreciated. Can’t wait to get back there this summer!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

John J.

Casco Bay Island Hideaway

Maine in the summer is pure magic, and I cannot think of a better place to enjoy a late summer family getaway than the Woodbury Cottage. Just a short ferry ride from Portland, you can enjoy total isolation at the cottage or all that the Maine city has to offer. It is the best of both worlds. The cottage is cute and private. It is decorated tastefully in a minimalist New England style. It is very comfortable place to decompress and relax. The home is devoid of the usual tacky second hand furniture and linens found in other rentals. The location (in the woods overlooking the water) and amenities on the Island (sandy beach, wooded areas, and friendly Mainers) offer a unique and relaxed setting. I have a six year old child and she really enjoyed the surrounding woods, coastline and wildlife of the island. It was very refreshing from the confines of NYC. Together we saw deer, osprey, snakes, grasshoppers and whole host of other critters from the sea. In the evenings, we dined on local fare and played the various board games in the rental owner’s provide collection. One small bit of advice is to plan in advance for groceries and getting your stuff (luggage and provisions) to the cottage. It is off a bit from the ferry (3-5 minute walk) and it is not an easy hike with children, provisions and baggage. Final note of endorsement is we are playing to rent this location again next summer.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Jill G.

Beautiful house, magnificent view, very thoughtful owner

My wife and I and our children stayed in the Woodbury for a week. The location of this cottage could not have been better. It is on a bluff over Casco Bay with magnificent, unobstructed views. One of my friends who visited us commented that she had never seen a house where the owner had been so thoughtful about supplying everything that we might have needed. The kitchen was well equipped and the owner provided a basket of personal items (shampoo, toothpaste, etc) in case we had forgotten anything.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

A true reboot!

We rented this house last summer. Quiet cabin in the woods! The views were incredible! It is a very nice clean and simple house. We have rented other houses through VRBO that are junked up with trinkets and this one definitely wasn’t. The owners were great about communicating things we might need and what the house already had—i.e. mentioned the tennis courts to bring our rackets, but was very thorough with what the kitchen had so we didn’t have to carry as much on the ferry. We would totally rent this house again—and probably will this year if our schedules line up!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Great Island Vacation Rental

We rented this house last year at the last minute. A few families that we knew were renting other houses on the island and we wanted to tag along, but there were no open rentals on the island. By word of mouth, we were put in contact with the owners who graciously agreed to rent to us. It is such an amazing retreat! It was perfect for us. We were able to get up in the morning, enjoy some quiet down time. We would have breakfast on the porch, enjoy our coffee and watch the boats go by. After that we would meet up with our friends and enjoy the island. Having the restaurant on the island was a huge bonus. We are so grateful that the owner shared their house with us! We are definitely going to go back this year!

About the host

Hosted by Jason O'Brien

Host profile image
Great Diamond Island is my favorite place on Earth. My grandfather bought The Woodbury Cottage with the intention of his family enjoying the island as much as he did and to continue to pass it down through the generations. While I get there as much as possible, unfortunately, I can't be there full time. So instead of letting it sit empty, I want to share this special place with others.

Why they chose this property

Not only is Great Diamond Island an amazing place, but The Woodbury Cottage is also located in one of the best spots on the entire island. It sits on the water's edge and is surrounded by 80 acres of wooded land. It's a quick 25-minute ferry ride from Portland but you feel like you're worlds away. So it's easy to get into Portland to explore if you want a break from island life. The cottage is secluded on Echo Point but Diamond Cove is located on the opposite of the island has 3 restaurants. It's the best of both worlds as you can out to eat but retreat back to total privacy and seclusion.

What makes this property unique

Situated on one of two adjacent family compounds, the seclusion and privacy that this property offers is unmatched by most. The cottage sits on waterfront property that offers unobstructed water views and is buffered by 80 acres of woods behind it. We have worked really hard to make it is stocked with everything guests need for an island escape. From a fully stocked pantry to all the best board games, there is everything you'll need so you don't have to worry about stressing over what to pack or waste time going back in town to get something.

Languages:

English
Tell us how we can improve our siteShare feedback