Winthrop Vacation Rentals Are Beautifully Situated on Annabessacook Lake

Imagine forested land surrounded by clear lake water, and you will start envisioning some of what you will find at Winthrop vacation rentals. Winthrop lodging is spread out over Kennebec County along Annabessacook Lake. When you take advantage of Winthrop cabins, you will be in one of the largest recreational areas in Maine because of the many lakes, villages, and hiking trails.

Viewing the Past Through Local Eyes near Winthrop Vacation Rentals


Historically, Winthrop vacation rentals have only been in the area for about 100 years, despite the area being settled in the 1700s. In 1765, a purchase was awarded by Plymouth Council for New England. The town was called Pondtown due to its lakes and ponds. Then John Winthrop settled in, calling it his home and during incorporation, the people changed the town’s name. It was mostly built on the industries of cattle, grain, apples, hay, and sawmills. Some of this can still be seen when you rent Winthrop lodging. Winthrop cottage rentals became popular as summer resorts after the Maine Central Railroad moved in.

Winthrop Lodging Offers Authentic Maine Vacations


Winthrop lodging varies from two bedrooms to four bedroom homes, with one or more bathrooms. Depending on the size of your group, you can find a romantic getaway or a reunion home. One option is an authentic Maine cottage with seven bedrooms and two bathrooms. Winthrop vacation rentals are on the waterfront with internet access and other modern amenities. All the rentals offer full kitchens with modern appliances, many with dishwashers. Televisions, VCRs, DVD players, books, and games may also be among the offerings for entertainment at the homes.

Enjoy Spending Time Outdoors at Winthrop Cabins


The idea of Winthrop cabins is to provide a wonderland of outdoor recreation. Visitors to Winthrop house rentals will be able to sit on a private beach, swim in the lake during summer, cruise around the lake or fish. Kayaking, hiking trails, and beautiful sunsets add to the attractions. Visitors are an hour from the ocean and mountains. In winter, skiing, both Alpine and Nordic, is possible near the rental of your choice.

Find more Kennebec vacation rentals and include Belgrade Lakes vacation rentals and Embden Lake rentals in your search.

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Winthrop: Cottages, Houses & More(18)

18 Results
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
1 Review
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 7
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
  • 3 BR,
  • 1 BA,
  • Sleeps 5
$1,155
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(6)
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
(8)
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 11
(15)
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
(7)
4 - 7 night minimum stay
  • 7 BR,
  • 2 BA,
  • Sleeps 15
1 Review
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 Reviews
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
$114 - $120
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
(8)
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(4)
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 10
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
(10)
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