Search Cottages in Windsor

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 34 Cottages in Windsor with updated reviews, rates, and availability.

Lakefront Connecticut Retreat Near UConn
Fridge, microwave, stovetop, dishwasher

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (17)
"This house on the lake was absolutely perfect! The location, view, and charming appointments made this one of our very best vacations. The owner cares deeply about this home and for the comfort of those who visit -- this shows in its cleanliness and thoughtful furnishings. We hope to return soon to this lovely home!"
Lakefront Connecticut Retreat Near UConn
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, (14)
"The place was great and we enjoyed the fishing."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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, (6)
"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
Reel Simple on Bolton Lake
Outdoor dining

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (23)
"Very nice house. Clean, nice backyard right on the lake. Nice and quiet at night!"
Reel Simple on Bolton 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)
"Nice cabin with great views of the lake. Enjoyed kayaks provided and the deck area. Well decorated and comfortable."
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Charming Cottage by the Lake❤️
Outdoor dining

Charming Cottage by the Lake❤️

9.8 out of 10, Exceptional, (11)
"Very cozy little home. "
Charming Cottage by the Lake❤️
Lake Getaway at Coventry Lake! close to Uconn
Exterior

Lake Getaway at Coventry Lake! close to Uconn

10.0 out of 10, Exceptional, (17)
"Nice spot, close to campus and perfect size."
Lake Getaway at Coventry Lake! close to 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!
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)
"Host were super friendly and very communicative"
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)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
Lakefront Connecticut Retreat Near Uconn
Cottage (2 Bedrooms) | Interior

Lakefront Connecticut Retreat Near Uconn

3.0 star property
Lakefront Connecticut Retreat Near Uconn
Our Cottage - Small in size, Big in character, On beautiful Highland Lake

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

10.0 out of 10, Exceptional, (43)
"Excellent place with modern decor inside and beautiful view of lake from very nice deck. Will definitely stay again! "
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Lakefront Granby Escape w/ Private Dock & Kayaks!
House (2 Bedrooms) | Front of property

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
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 Cottage w/ Covered Porch & Dock!
Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
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.
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
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
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!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start packing for a memorable vacay close to nature. If you have a certain budget, select how much you want to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect digs whatever your getaway looks like.
How can I find cheap cottages in Windsor?
The best way to locate cheap cottages in Windsor is with Expedia’s convenient filter tool. Refine your search results by star rating, amenities and budget to take advantage of awesome prices in a couple of clicks.