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Holiday rentals in Winthrop

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Top-rated holiday rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness, and more.

Island A-frame in Maine
SUPERHOST
Tiny house · 4 guests · 2 beds · 1 bathroom
Island A-frame in MaineWelcome to the A-frame at the Gazebo on our private island in Maine. Sleep comfortably, cook your favorite meals, hang in the hammock, sit by the fire, listen to the loons call, enjoy the hospitality of experienced Superhosts and Maine Guides, play on the rope swing, canoe or kayak the lake, and walk the trails of this 14 acre wooded island. We greet all guests in our safe parking area on the shore of the lake, help move you and your gear to the island. We'll guide you until you are settled.
Island Tree House in Maine
SUPERHOST
Treehouse · 4 guests · 2 beds · 1 bathroom
Island Tree House in MaineRest easy in the Oaktagon Tree Yurt of 1 Big Sustainable Island. This off the grid (no electricity) one-of-a-kind home is perched on a 14 acre, semi-private island 1/2 mile from shore on a Maine lake. The 900 sq. ft. octagonal home, built around a living Red Oak tree, is designed to make your stay comfortable, relaxing, and soothing. It has the sights & sounds of the best of Maine's natural beauty: fresh air, clean water, the nature of woods, and the sounds of loons on a quiet lake.
Private Island Log Cabin in Maine!
SUPERHOST
Island · 4 guests · 2 beds · Toilet with sink
Private Island Log Cabin in Maine!Little Cabin is on a small island on Annabessacook Lake in Maine. Enjoy pristine surroundings and a rustic, off-the-grid cedar log cabin. Take a blissful private adventure - swimming, boating, fishing, birding, and relaxing by the fire. NEW THIS YEAR - LIMITED SOLAR LIGHTING!

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Winthrop holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Winthrop

SUPERHOST
  1. Barn
  2. Winthrop
Definitely not glamping, but rustic building camp
₹2,925 per night
SUPERHOST
  1. Entire guest suite
  2. Wayne
Hooker's Point on west side of Pocasset Lake
₹7,650 per night
SUPERHOST
  1. Entire residential home
  2. Wayne
Peaceful Getaway at The Ledges
₹10,500 per night
SUPERHOST
  1. Entire rental unit
  2. Wayne
Serenity Lake House Apt Lake views from all rooms.
₹10,500 per night
SUPERHOST
  1. Hotel room
  2. Hallowell
Maple Hill Farm Inn, Room 5, Sauna+Outdoor Hot Tub
₹13,532 per night
SUPERHOST
  1. Tiny house
  2. Winthrop
Two Cedar Tiny House
₹7,125 per night
SUPERHOST
  1. Tent
  2. Monmouth
Island Luxury Tent in Maine Solitude
₹7,425 per night
SUPERHOST
  1. Dome house
  2. Readfield
Maranacook Lake home w/deck and dock
₹16,125 per night
SUPERHOST
  1. Entire residential home
  2. Monmouth
The Cottage at Red Top - Cozy Lakeside Charm
₹20,625 per night
SUPERHOST
  1. Entire residential home
  2. Monmouth
Spacious Lakeside Comfort - Maine's Finest
₹29,625 per night
SUPERHOST
  1. Entire cabin
  2. West Gardiner
Nature Lovers Paradise Lake Island
₹13,093 per night
  1. Entire cottage
  2. Monmouth
Relax, you're on the water!
₹11,625 per night