Perfect island cottage on the water`s edge surrounded by nature.

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Guests 8
Bedrooms 3
Bathrooms 2
Allows Pets Yes


Serendipity is your perfect Maine getaway – a cottage by the water, on an island, yet reachable by car. Located on Montsweag Bay, it is surrounded by the Sheepscot River to the East and both Back River and the Sasanoa Rivers to the West, all of which are tidal salt water. Westport Island is a quiet and picture perfect small Maine community of about 800 year round residents. It was originally known as Jeremy Squam and noted to have flourished in the early 1800`s as a fishing and farming community; one of the most prosperous in Maine. Today it is home to a broad cross-section of residents from families who have lived there for generations to new residents and retirees who are proud to call Westport Island home.

The owners of this three bedroom, 2 bath cottage have thought of everything to make your vacation memorable. From comfortable seating in the living room and on the deck to a "mosquito-proof" screened gazebo at the water’s edge where you can enjoy the views, a glass of wine, or a meal without the addition of Maine`s "unofficial State bird." There is a dock and float from which you can swim, fish or launch either the kayak and canoe that are there for your enjoyment, a means to explore this wonderful area. Don`t be surprised to find eagles flying overhead or a Great Blue Heron fishing there at low tide. The Squire Tarbox Inn is a restaurant of local renown that serves dinner to the public and is just a short distance away. In the town of Wiscasset one can stop by for one of Red`s Eats famous lobster rolls, stop by Sarah's for soup and sandwich,  or do some shopping or antiquing. Boothbay Harbor is only a short drive to the East and LL Bean in Freeport is to the West. Go to the Maine State Musical Theater for a summer show or visit the state Capitol and buildings in Augusta (North of Wiscasset).  There is a lot to see and do and we have been told by our guests that they find themselves saying "We have to come back next year, there was not enough time to do everything we wanted."

Queen, Double, Queen, 2 singles (In a Trundle bed)

First Floor - Full
Lower Level - Full

Maine is famous for her coastal islands and Westport Island is a prime example. Located in the middle of the tidal, saltwater Sheepscot River, you will not tire of all there is to do and see! Rent a couple kayaks or even hire a guide and explore this rich and bountiful region of mid-coast Maine. Island living is its own kind of magic!

Water access is available from Wright Landing, less than a mile from the house. This public landing has a dock and float, boat launch and picnic areas with more incredible views! The MacNamara Foundation (summer artists’ colony) is close by as is the Clough Point Preserve for hiking, views and exploration! A short drive brings you to Wiscasset for great dining, Antiquing and shopping. Head the other direction and find yourself in historic Bath or head over to Popham State Beach or Reid State Park -both have long stretches of white sandy beaches! Boothbay Peninsula is also close by with shopping, walking trails, whale watching and more. Day trips via the Downeast Express from Wiscasset to Damarisoctta and on to Rockland or south to Boston with stops in Brunswick, Freeport and Portland are an option as well.

Peruse our web site for local vendors, eateries and activities. Replete with all things vacation; if you can think of it, our site most likely covers it! Be sure to reach out to us if you need any help creating the perfect vacation!

Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993.
Cottage Connection was one of the first vacation rental companies in the Mid-coast region of Maine. Jeff and Audrey Miller, who own three vacation rental homes themselves had an aha moment when they realized they could not find anyone who ‘got it’ to manage their rentals for them. Since 1993 they have been trusted by homeowners and vacationers to “connect” each family with the perfect cottage for their vacation. As Audrey puts it; “The home they stay in becomes a personality, a part of their lore, when a family connects with the right cottage. Whether they want a rustic cabin in the woods or a high-end ocean bungalow, the right setting sets the tone for the entire vacation.” Learn more about how Cottage Connection can help make your vacation perfect!

The Boothbay Peninsula is a beautiful region rich in culture, history, all things nautical and of course it’s own unique niche in nature. The area offers ample opportunities for biking, kayaking, canoeing, fishing, charters and guided cruises, spas, a championship golf course and country club, mini-golf, bowling, museums, antiquing, hiking and walking trails. We have the Maine State Aquarium, the Coastal Maine Botanical Gardens and the Boothbay Region Land Trust with its 30+ miles of pet friendly trails in protected areas. For a more comprehensive list of local offerings Click Here!

Westport Island is 14.2 square miles and has a population of just under 750 people and nestles in the Sheepscot, a tidal salt-water river. Accessible via bridge from Wiscasset, or via boat from just about anywhere, it is just off Route One which affords easy access to mid-coast Maine while still giving a sense of remote, peaceful tranquility. Still referred to by the locals as Jeremysquam, the island has a rich nautical history and a deep love of the sea’s bounty. The island has a couple distinguished eateries including the famed Squire Tar Box Inn. Also close by is the MacNamara Foundation where you can watch, or join, artists at work using various mediums. Within an easy drive, or scenic boat ride, are Wiscasset, Damariscotta, Boothbay and more! You can also make easy trips to the Maine Maritime Museum in Bath, Popham Beach and Reid State Park.


Pet Friendly
Full Kitchen
Gas Grill
Washer / Dryer
Working Wood Fireplace/ Wood provided
Private Dock and Float
Screened Gazebo at water's Edge
Flat Screen TV
Basic Cable
Canoe / Kayak
No room in your luggage or car for linens? Order them today for your stay.

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Write a Review
Tim & Tracy
Reviewed: Jul 8, 2015
Property Manager
Check in and check out was easy. The reservation and stay went smoothly.
Very comfortable beds. We would return, it was a sweet cottage to vacation at in a very quiet area. One of our favorite things to do while at Serendipity was kayaking with my kids. They loved getting around in the water and trying to go to other areas in the water.


Check-In Day:  FridaysJune 24-Sept 5, 2016 (Prime Season Week’s).  See below for shoulder season details

Check-In Time: BEGINS 4:00 PM during prime season

Check-Out Time:  no later than 10:00 AM
Town:    Westport Island

Body of water:    Montsweag Bay

Bays are usually a recess in the coastline that opens directly into the ocean.  

Type of Waterfront:   Rocky Ledge - Dock & Float

Swimming Area Rating for this property is a…,   1

5 – very easy water access, sandy or pebble beach, great for all ages!
4 – Easy water access, may be a pebble beach or grassy shoreline. Still good for all ages, but young children may want water shoes.
3 – Somewhat easy water access with a rocky shoreline, or rocky bottom, not suitable for young children, but fine for older children/adults, water shoes recommended.
2 – Water access only for agile young adults or adults, rocky shoreline or bottom, may be a hill down to the water or subject to strong currents.
1 – Swimming off dock only due to a seawall or rocky/wooded shoreline, owner has provided a swim ladder to make getting in and out of water easier. 
0 – not a waterfront property.

Privacy rating for this property is a…,   5

5 – very private, secluded location, lots of protection from trees, cannot see any neighbors from the house, not close to any roads, long driveway.
4 – Private location, protection from trees, neighbors a comfortable distance away, not close to any roads.
3 – Still in a quiet location, but one neighbor close by, little protection from trees, may be close to a road.
2 – Semi-quiet location, neighbors close by, may have road noise.
1 – in-town home, little or no privacy

# of Bedrooms:  3
Bed Sizes:  (2) Queens (1) Double (2) Singles (within a trundle bed)

# of Bathrooms:  2
Bathroom Type:  Full baths

Smoking AND/OR Fireworks Are Prohibited on EVERY Property

Cottage Connection of Maine represents a wide variety of quality vacation rentals throughout the Mid Coast Region of Maine. Individually and privately owned, each vacation rental reflects the taste of its property owners. Every effort has been made to ensure that the descriptions and amenities listed are accurate. However, occasionally changes are made by the owners to furnishings, amenities and equipment. Once a change that has occurred is brought to our attention, we will update that webpage. If you have any specific questions not addressed above or are in search of specific criteria, please contact us.

In other seasons (Spring or Fall), arrival dates may be flexible, speak to the reservationist.  Also, if you book a 7 night stay in the shoulder season, a 15% discount will be applied to your weekly rate.

This house is pet friendly   /  Linens (sheets and towels) are NOT provided for your stay - order them today from Cottage Connection to save room in your luggage or car  /  Canoe and Kayak for guests use - recommended that you bring your own flotation devices (life vests) to insure fit and condition.  

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