Cottage in Winchester, CT
6 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this cottage rental
Escape to our cozy, completely renovated cottage on beautiful Highland Lake. Small in size but big in character, it’s a peaceful waterfront getaway that’s especially loved by couples and perfect for friends or a small family.
Wake up to quiet lake views and enjoy coffee on the deck, spend the day exploring the Litchfield Hills, and come home to some truly spectacular sunsets.
Inside you’ll find two bedrooms with full-size beds, a queen sleeper sofa with memory-foam topper, and a fully equipped kitchen with double oven and full spice rack. Outside, enjoy the spacious walk-out deck, private dock, gas and charcoal grills, and—during the warmer season—kayaks, fishing and boating.
We also provide a complimentary coffee & tea setup with assorted K-Cups, ground coffee, assorted teas and chilled bottled water.
Fall is a beautiful time at Highland Lake. The summer crowds disappear, the surrounding hills change color and the lake becomes wonderfully peaceful—perfect for a romantic getaway, girls’ weekend or simply a few days away.
PLEASE NOTE: Highland Lake’s scheduled 2026/2027 drawdown begins November 1, 2026, with a maximum drawdown of 36 inches. Water levels and some lake activities may be affected.
All fees are included. No hidden fees.
Wake up to quiet lake views and enjoy coffee on the deck, spend the day exploring the Litchfield Hills, and come home to some truly spectacular sunsets.
Inside you’ll find two bedrooms with full-size beds, a queen sleeper sofa with memory-foam topper, and a fully equipped kitchen with double oven and full spice rack. Outside, enjoy the spacious walk-out deck, private dock, gas and charcoal grills, and—during the warmer season—kayaks, fishing and boating.
We also provide a complimentary coffee & tea setup with assorted K-Cups, ground coffee, assorted teas and chilled bottled water.
Fall is a beautiful time at Highland Lake. The summer crowds disappear, the surrounding hills change color and the lake becomes wonderfully peaceful—perfect for a romantic getaway, girls’ weekend or simply a few days away.
PLEASE NOTE: Highland Lake’s scheduled 2026/2027 drawdown begins November 1, 2026, with a maximum drawdown of 36 inches. Water levels and some lake activities may be affected.
All fees are included. No hidden fees.
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Winchester, CT
Ratings and reviews
10 / 10Outstanding·Nov 2025
Such an amazing modern cottage. The lake view was spectacular amd the warm vibe of the cottage itself was amazing. We will for sure look to book this property again in the near future to see our cousins again.
10 / 10Outstanding·Nov 2025
Beautiful cottage. Host was very helpful and accommodating.
10 / 10Outstanding·Oct 2025
This place was spotless. Newly rebuilt I would guess. So well stocked that I cannot even imagine something that was not there. We came in the Fall so it was very quiet. The host was fantastic and offered to let us come in early. When we got a flat tire from in town on our last morning she offered to let us stay inside all day as we waited for AAA. She could not have been more accommodating. We would easily stay here again.
10 / 10Outstanding·Sep 2025
Very good
$$$$
Top rated by guests
10Outstanding
(49 Ratings)
"Such an amazing modern cottage. The lake view was spectacular amd the warm vibe of the cottage itself was amazing. We will for sure look to book this property again in the near future to see our cousi..."
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