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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

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

Charming Cottage by the Lake❤️
Outdoor dining

Charming Cottage by the Lake❤️

9.6 out of 10, Exceptional, (8)
"Very cozy little home. "
Charming Cottage by the Lake❤️
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Fridge, microwave, stovetop, cookware/dishes/utensils

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!
Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Lakefront Connecticut Retreat Near UConn
Fridge, microwave, stovetop, dishwasher

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (14)
"We stayed for 2 nights while my daughter was swimming at UCONN. Place was clean and warm and had everything we could need. Short drive to campus and beautiful views of the frozen lake!"
Lakefront Connecticut Retreat Near UConn
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beach nearby, sun loungers, beach towels

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
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous

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!
Reel Simple on Bolton Lake
Outdoor dining

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (22)
"We were a little nervous upon arrival, it was exceptionally cold that day Dec 22nd, 2 deg at night ,and we were afraid it wouldn't heat up. However, between the heat pumps and the electric fireplace, it became toasty! Very convenient, 2 bathrooms great !We would definitely book again !"
Reel Simple on Bolton Lake
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Shower, hair dryer, towels, soap

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.
Lakefront Tranquility/Fishermans Delight
Lake

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
Lake Getaway at Coventry Lake! close to Uconn
Exterior

Lake Getaway at Coventry Lake! close to Uconn

10.0 out of 10, Exceptional, (17)
"This cottage is adorable-beautifully decorated and well appointed. I seriously want to hire whoever decorated this house for my house! Excellent communication with the owner. We stayed in January and it was cold!! The gas logs made it nice and toasty, but it took us a while to figure them out, written instructions on how to turn on the fireplace would have been helpful-but other than that we had a great stay! "
Lake Getaway at Coventry Lake! close to Uconn
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Lakefront Connecticut Retreat Near Uconn
Cottage (2 Bedrooms) | Interior

Lakefront Connecticut Retreat Near Uconn

3.0 star property
Lakefront Connecticut Retreat Near Uconn
Lakefront Cottage w/ Covered Porch & Dock!
Miscellaneous

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!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Living area

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Lakefront Granby Escape w/ Private Dock & Kayaks!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Cottage (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, cookware/dishes/utensils

Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!

3.0 star property
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!
Charming Farmington Home ~ 5 Mi to Uconn Health!
Interior

Charming Farmington Home ~ 5 Mi to Uconn Health!

3.0 star property
Charming Farmington Home ~ 5 Mi to Uconn Health!
Family Home w/ Deck & Grills in Southington!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Family Home w/ Deck & Grills in Southington!

3.0 star property
Family Home w/ Deck & Grills in Southington!
Springfield Vacation Rental: 1 Mi to Downtown
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
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

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (13)
"I had such a good time here that I actually added three more weeks so this is the first of three reviews as I booked them separately. The host was really nice working with me and the associate that supports any household requests as well. Everything works perfectly, but the host associate was nice to come and anticipate the batteries on the smart lock would be running low and came and changed them along with leaving me extra snow melt, and a shovel after clearing the walkways. The house is well...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Fridge, microwave, oven, stovetop

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Island Vibes Home
Interior

Island Vibes Home

9.2 out of 10, Wonderful, (14)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home
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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