Maine Places

Cushing Glass House

You Could Stay Here

Maine Places

When I was a kid, my happiest summer week was the one when we packed up our minivan and headed for a rental on Long or Sebago Lake. Rather than invest in a camp, my parents liked to try out different spots — and leave at the end of our stay without worrying about paying the mortgage or closing up the place. Our first stop on such trips was always Krainin Real Estate in Raymond, where we picked up keys, got directions to “our camp,” and advice on where to eat out and acquire provisions. While researching this story, I was delighted to discover that Krainin and many other Maine vacation rental agencies are still thriving in the age of Airbnb, Home Away, and VRBO. According to our recent article, Home Advantage, these companies help homeowners and renters by streamlining the booking process, ensuring that properties are clean and in compliance with safety codes, and providing the kind of concierge service my family experienced all those years ago. As for the rentals they offer, I found everything from an adorable Crescent Lake cottage that was pictured in an L.L. Bean catalog to a contemporary marvel on Muscongus Bay (above) designed by internationally acclaimed architect Toshiko Mori. Here’s the lowdown on those properties and a few more of my favorites.

Crescent Lake cottage

Crescent Lake cottage
Crescent Lake cottage
Crescent Lake cottage
Crescent Lake cottage

Haskell Avenue, Raymond

Setting: Cottage and guest house on Crescent Lake. 3 bedrooms, 1 ½ baths, fireplace, screened porch, dock, canoe, kayak.

Sleeps: 8

Weekly rate: $900-$1,600

Photos courtesy of Krainin Real Estate

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Northport cottage

Northport cottage
Northport cottage
Northport cottage
Northport cottage

North Avenue, Northport

Setting: Oceanview cottage in quaint Bayside neighborhood. 3 bedrooms, 2 baths, gas stove, wraparound porch.

Sleeps: 5

Weekly rate: $1,075-$1,550

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Photos courtesy of Bayside Cottage Rentals

Higgins Beach cottage

Higgins Beach cottage
Higgins Beach cottage
Higgins Beach cottage
Higgins Beach cottage

Champion Street, Scarborough 

Setting: Bungalow near Higgins Beach. 2 bedrooms plus a loft, 1 bath, fireplace, deck.

Sleeps: 6

Weekly Rate: $1,300-$2,400

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Photos courtesy of Scott & Sunny Townsend Team

West Bath cottage

West Bath cottage
West Bath cottage
West Bath cottage
West Bath cottage

Birch Ledges Drive, West Bath 

Setting: Oceanfront cottage designed by a sailor to evoke living on a boat. 2 bedrooms, 1 bath, gas stove, deck.

Sleeps: 4

Weekly Rate: $1,475-$1,575

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Photos courtesy of Cottage Connection of Maine

Westport Island home

Westport Island home
Westport Island home
Westport Island home
Westport Island home

Tarbox Road, Westport Island

Setting: Oceanfront 19th-century Greek Revival farmhouse. 3 bedrooms, 2 baths, woodstove, hiking trails.

Sleeps: 6

Weekly Rate: $1,475-$1,925

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Photos courtesy of Cottage Connection of Maine

Deer Isle camp

Deer Isle camp
Deer Isle camp
Deer Isle camp
Deer Isle camp

French Camp Road, Deer Isle

Setting: 1930s-era former French camp on Penobscot Bay. 4 bedrooms, 2 baths, fireplace, deck, dock, rowboat.

Sleeps: 8

Weekly Rate: $1,500-$1,900

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Photos courtesy of The Island Agency

Cushing Glass House

Cushing Glass House
Cushing Glass House
Cushing Glass House
Cushing Glass House

Davis Point Road, Cushing

Setting: Toshiko Mori-designed “Glass House” on Muscongus Bay. 3 bedrooms, 2 baths, gas stove, boat mooring.

Sleeps: 6

Weekly Rate: $1,500- $2,500

Learn More

Photos, including cover image, courtesy of On the Water in Maine

See any place you’d like to stay? The prime booking season for summer rentals in Maine is January through May, so now’s the time to plan your trip! Good luck and let me know where you end up.


3 Comments

  1. Sarah:

    Literally, strange but true:

    The Dr. Robert and Regina Chisholm did the same thing on/ at Sebago Lake, with my five brothers, until we bought land in Spruce Head, and then the cottage on Timber Point Road in Friendship ( which we enjoyed some 40 plus years).

    I put a call in on the Portland property. The call got dropped. Of course, I will call again.

    Steve Chisholm

  2. Sarah Stebbins

    How cool, Steve! You really do have deep roots here and I can see why you want to move back. Re: the property, try this number, too. I think it may be the agent’s cell: 207.838.1050. Best of luck and let me know how it turns out!

  3. Serena Joyce

    A big part of the rental experience are the people from whom you rent. Ease and transparency of communication are key in addition to being as present or absent as you wish. I was DELIGHTED to see the Scott and Sunny Townsend Team included in your selections. They have assisted me for the past decade and I cannot recommend them highly enough.

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