Southport Island, Maine: Finding The Perfect Rental

By Kent E. St. John

The author's cozy cottage on Southport Island, Cozy Harbor Maine
The author’s cozy cottage on Cozy Harbor – photos by Kent E. St. John.

I wasn’t asking for much when I looked into renting a place on the coast of Maine. Only that it be reasonably priced, on the water, full of charm, fully stocked, and near a town with activity; in other words a fantasy rental.

Determination and hours online paid off when I came across Cozy Cottage on Cozy Harbor on Southport Island, Maine. I went through the pictures several times until I realized that I better jump and quickly; the chance of an opening in July was tenuous at best.

The next morning I received an email from the cottage’s owner that my desired week was still open. Bingo! A chance to be a summer person near one of Maine’s prettiest costal villages, a carefree week by the ocean, so the check was in the mail.

Not very long after, I was awaiting John and Ellen Blois at the Hannaford Store in Boothbay Harbor to get the keys to my home on the coast of Maine.

Love at First Sight

We trailed the Blois through Boothbay Harbor and then came to the swinging bridge that took us to Southport Island; the four short miles to the cottage took us far from Boothbay’s busy visitor packed streets.

As Lil and I followed to the small, heavily wooded peninsula the turn of the century cottage greeted us with the sun gleaming off its coat of fresh white paint. After a quick tour from John and Ellen we quickly did our own tour of the Cozy, followed by a stroll of the massive green lawn down to the waterfront.

The rental on Southport Island was a perfect place for sea kayaking.
The rental on Southport Island was a perfect place for sea kayaking.

The smile on my wife’s face said it all — I was a travel god! After pulling our kayaks down to the water’s edge, we immediately knew that dinner that night was going to be at HOME. Part of the fun of renting is the ability to make that very choice.

The Benefits of a Complete Package

The second factor of my fantasy rental was covered; all supplies and needs were met. Make sure to find out what is included and what isn’t: Who wants to lug pots, pans, linen and towels in a jeep filled with kayaking gear?

The cottage had two bedrooms, kitchen, living room and bathroom. The second bedroom came in handy for visitors. Just as important is to be very sure about what is expected of you as a renter: If Fido isn’t allowed board him. If smoking isn’t allowed inside, don’t.

People who rent out homes have a vast amount of money involved. Put yourself in their place—what if you went home and found caca everywhere? There is only so much coast of Maine available, so news of bad renters is shared.

Think of Axel Rose and hotels now not available to him. Build a relationship with the real owners of your summer retreat. In my case, I already know that I will return next season and I got all of my deposit back!

Cozy Harbor
Cozy Harbor, Maine.

Southport: Location, Location, and Location

If it sounds like I am selling you real estate I must admit I am not licensed, but the rental game is the same. If you really want to enjoy a rental, know the area. Before you commit, check online to see what is nearby.

In my case, I wanted a place to kayak without loading the jeep again. Of course, I knew from the site that I could just drag them in but was happily surprised that I had a picturesque harbor a few strokes away. Depending on the tides I could watch lobstermen gear up or future yachtsmen sail in bathtub size crafts.

We also had several other nearby necessities that made those hours of searching pay off. The walk to a nature trek was on my list, and from Cozy on Southport Island, it was a two-minute walk to one of Boothbay Harbor’s Trust Nature Walk trails.

Henndrick's Head lighthouse on southport island Maine.
Hendrick’s Head lighthouse

Better yet was the five-minute stroll to Hendricks Head Beach and lighthouse, perfect for hot sunny days and used by locals. The nearby Southport Country Store had everything needed for any occasion.

By far the activity we enjoyed most was just sitting on the massive lawn and watching Cozy Harbor life. That would’ve been the case except for a list of activities made before we arrived.

Out and About on Southport Island

One my favorite activities is kayaking, and one of the best places to do it is the coast of Maine. We had our own but if you don’t, there are many available for rent in Boothbay. One of the best companies in the area is situated right on the harbor in East Boothbay.

The East Boothbay Kayak Company offers both rentals and guided tours for both beginners and advanced. If renting a place consider a weekly rental, they will deliver kayaks for an extra $20 charge. The thrill of gliding over the rolling tides is unbeatable and for our next adventure, a kayak is necessary. The East Boothbay Kayaking Company is on Rte. 96, East Boothbay, 207 633- 7140.

If exploring an island filled with natural and supernatural wonders, you’ll be glad to know about the East Boothbay kayaking Company. The only way to get to Damariscove Island is by water.

This 209-acre island was the home to Damerill’s fishermen; they supplied cod to the starving settlers at Plymouth Plantation, well before the turkey carving days! For years stories about the ghost of Captain Richard Pattishall, beheaded by Native Americans in 1689, have captivated those who have wandered the island in the fog.

In summers Southport island is covered with wildflowers, raspberries, and rugosa roses. The Island is owned by the Nature Conservancy and information can be found at

For a controlled island experience with a great peek into the past, Burnt Island is the ticket. On the tour, you will get a look into the life of a lighthouse keeper and his family in the 1936-1951 period. It is a three-hour tour done with costumed guides that include a trip to the lighthouse tower, not hokey at all! The program was designed and run by the Maine Department of Marine Resources and is run twice daily.

Lobsterboats in Cozy Harbor
Lobster boats in Cozy Harbor

You’ll find yourself screaming, “Thar she blows!” when massive mammals known as whales peak up from far below. Cap’n Fish’s Whale Watching trips are on modern and comfortable crafts and ended the 2005 season with a 98% success rate of sightings.

If you happen to be in that 2% that was unlucky they offer a rain check on another trip. It can get cold out on the ocean so bring layers of clothes.

The Finer Side of Southport

There is a saying in Maine that if you don’t like the weather, wait five minutes and it will change. On the one rainy day we had we spent time strolling and shopping in Boothbay Harbor. While there is an abundance of tacky tee shops, there are also some fine shops and galleries. Two of my favorites were the Abacus on 12 Mckown Street and Edgecomb Potters Gallery on Rt. 27; we spent hours picking up various mementos.

Perhaps because Cozy Cottage was so cozy, we shopped at farmers’ markets and lobster co-ops and cooked at our rental home often; beating our own waterfront setting was hard to do!

There were, however, two places to dine that were stellar and both were on Southport Island. Top of my short list is the Newagen Inn on Rt. 27. The dishes were a wonderful blend of Asian and local catches from the ocean. It was relaxed and sends you back to a period of time that has passed by elsewhere.

The second was the Lawnmeer Inn also on Rt. 27 in Southport. Water views and a vast menu make for a happy traveler. The place was bustling and lively so reservations, at least in July, are a must.

Often as a travel writer, I share some places I wish I could keep a secret and Cozy Harbor Cottage is one. I absolutely will be back there next summer and if possible for two weeks so be forewarned, book soon.

For other Maine rentals go to

For info on Boothbay click on 

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