The Woodbury Cottage: An Oceanfront Maine Island Escape

3 bedrooms2 bathroomsSleeps 6

Popular amenities

Kitchen

Barbecue grill

Free WiFi

Washer

Dryer

Outdoor space

Explore the area

Portland, ME

Sand Beach4 min drive
Casco Bay Lines Ferry Terminal42 min drive
Cross Insurance Arena43 min drive
Portland, ME (PWM-Portland Intl. Jetport)49 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 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

Amenities

Kitchen

Washer

Dryer

Free WiFi

Outdoor space

Ocean view

Ocean view

Kitchen

Washer

Dryer

House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

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.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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. Casco Bay Lines Ferry Terminal and Children's Museum and Theatre of Maine are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Mackworth Island State Park and Casco Bay. 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.

Portland, ME

What's nearby

Sand Beach - 4 min drive
Casco Bay Lines Ferry Terminal - 42 min drive
Merrill Auditorium - 42 min drive
Cross Insurance Arena - 43 min drive
State Theatre - 43 min drive

Getting around

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

Restaurants

Lolita-Munjoy Hill - 32 min drive
Brickyard Hollow Brewing Company - 26 min drive
Twelve - 27 min drive
Saltwater Grille - 38 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 3:00 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 is 1.3 mi (2.1 km) away.

10

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

Samuel H.

30 July 2023

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.

30 June 2022

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.

11 Aug 2021

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

1 Aug 2019

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.

8 July 2019

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

About the host

Hosted by Jason O'Brien

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.

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