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Compare 30 Cottages in Windsor with updated reviews, rates, and availability.

The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Lakefront Connecticut Retreat Near UConn
10.0 out of 10, Exceptional, (13)
"Amazing place and view. Entire stay was great to share while in for family weekend. Very welcoming and hospitality. 10!"
Lakefront Connecticut Retreat Near UConn
Charming Cottage by the Lake♥️
9.8 out of 10, Exceptional, (7)
"Very nice and clean cottage. Loved the coziness,and it was close to the university where went to a girls basketball game,go Huskies! Host was quick to respond back with questions I had. We had a very enjoyable time. Would definitely return."
Charming Cottage by the Lake♥️
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
9.4 out of 10, Exceptional, (23)
"We thoroughly enjoyed our stay. This cottage perfect for two people. The location has all the amenities you could ask for. Climbing up and down the 43 steps to cottage can be tiring especially for the elderly. There is Liquer store very close buy and grocery store within 5 miles. I must say that prices there very high, but in no way does that reflect on owner. We certainly are looking forward to coming back for another stay."
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
The Little Red Cottage
10.0 out of 10, Exceptional, (4)
"This place was so cute! The pictures don't do it justice. The layout of the house is perfect. The rooms are spread out so your not on top of each other with larger groups. Each room has an a/c which was so nice. This house is in a great location, in such privacy, but so close to stores, food, and shops. Will definitely be back. Thanks so much Jodi for being so communicative and opening your doors to my family and I. See ya soon!!!"
The Little Red Cottage
Lake Getaway at Coventry Lake! close to Uconn
10.0 out of 10, Exceptional, (13)
"Nice spot, close to campus and perfect size."
Lake Getaway at Coventry Lake! close to Uconn
Lakefront Cottage w/ Covered Porch & Dock!
10.0 out of 10, Exceptional, (13)
"Small quaint cottage on lake. Very peaceful. Owner was very attentive."
Lakefront Cottage w/ Covered Porch & Dock!
Lakefront Tranquility/Fishermans Delight
9.8 out of 10, Exceptional, (18)
"The cabin was simple, clean, and cozy. A great place to slow down, and enjoy a simpler lifestyle with a beautiful view of the lake. We hope to return during the summer when we can enjoy the lake fully. "
Lakefront Tranquility/Fishermans Delight
Charming Farmhouse w/ Pool & Fishing Pond!
3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Lakefront Connecticut Retreat Near Uconn
3.0 star property
Lakefront Connecticut Retreat Near Uconn
Lakefront Granby Escape w/ Private Dock & Kayaks!
3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Reel Simple on Bolton Lake
2.0 star property
9.6 out of 10, Exceptional, (20)
"Very nice house. Clean, nice backyard right on the lake. Nice and quiet at night!"
Reel Simple on Bolton Lake
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
2.0 star property
9.4 out of 10, Exceptional, (3)
"Our stay was super easy. Not a far walk to the beach. Communication was super fast and easy as well! Only a slight musty smell in the big bedroom, but not enough for me to take off any stars. "
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Charming Windsor Home w/ Private Backyard!
3.0 star property
Charming Windsor Home w/ Private Backyard!
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
3.0 star property
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Springfield Vacation Rental: 1 Mi to Downtown
3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Family Home w/ Deck & Grills in Southington!
3.0 star property
Family Home w/ Deck & Grills in Southington!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windsor

A “Wow” Experience everywhere there is something to stimulate your mind Interest
9.0 out of 10, Wonderful, (2)
"Great property and a great location. The host was more than welcoming and very easy to communicate to. This was our second visit to this location and we plan to stay again if availability allows. "
The price is SAR 1,078
SAR 2,094 total
includes taxes & fees
17 Nov - 18 Nov
A “Wow” Experience everywhere there is something to stimulate your mind Interest
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Bungalow House - Free Parking - 10 mins to Hartford & Airport
8.0 out of 10, Very Good, (22)
"House was very clean. Everything was as described and the Owner was very responsive to our requests pre checkin."
Bungalow House - Free Parking - 10 mins to Hartford & Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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