Search Windsor Cottages

Compare 24 Cottages in Windsor with updated reviews, rates, and availability.

Lake
Lakefront Tranquility/Fishermans Delight
9.8 out of 10, Exceptional, (14)
"The cabin was just what we needed to escape the hustle and bustle of work!! Just the right size to sit and relax by the water and enjoy an early morning or late evening canoe ride while the Eagle flew above us. Perfect spot for day hikes or day drinking at the wineries. Then enjoy a bonfire with a glass of wine and talk about all you did and what you want to do the next day!! Definitely recommend and will be back"
Lakefront Tranquility/Fishermans Delight
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (7)
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Fridge, microwave, oven, stovetop
The Little Red Cottage
10.0 out of 10, Exceptional, (3)
"Just a couple miles from campus, great locale for a family stay. Bonus chocolate pretzels upon arrival appreciated. Very great communication from hosts. It is an older cottage w quirks of an older house w original bathroom w no mirror, steep staircase to basement off the kitchen, small TV, but great for playing some games and close place to sleep/shower."
The price is $209
$302 total
includes taxes & fees
Jun 10 - Jun 11
The Little Red Cottage
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Lake Getaway at Coventry Lake! close to Uconn
10.0 out of 10, Exceptional, (4)
"House was beautiful and well-accommodating. Minutes from campus. Proximity to lake was a plus! Owner responsive and pleasant. Would stay here again!"
Lake Getaway at Coventry Lake! close to Uconn
Fridge, microwave, stovetop, dishwasher
Lakefront Connecticut Retreat Near UConn
9.8 out of 10, Exceptional, (9)
"We had a wonderful weekend at our daughters graduation from U Conn & the house was perfect for our needs ,beautiful lakeside location ,clean & comfortable,the hot tub was a welcome bonus !! We really appreciated the lovely hospitality of the owner ,who left balloons & Prosecco out to greet us on our arrival !!"
Lakefront Connecticut Retreat Near UConn
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!
Beach nearby, sun loungers, beach towels
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (3)
"happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water."
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Property grounds
Lakefront Cottage w/ Covered Porch & Dock!
10.0 out of 10, Exceptional, (9)
"Everything about the cottage was perfect for our graduation weekend and family get together. Susan thought of every detail and made it a home away from home. We will definitely be back. The beauty and peacefulness of waking up to the sun on the lake will remain in my memory. Even the cloudy mornings and the light rain on the roof were delightful. "
Lakefront Cottage w/ Covered Porch & Dock!
Property grounds
Charming Cottage by the Lake♥️
Charming Cottage by the Lake♥️
Interior
Charming Farmhouse w/ Pool & Fishing Pond!
3.5 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Interior
Lakefront Connecticut Retreat Near Uconn
3.0 star property
Lakefront Connecticut Retreat Near Uconn
Interior
Lakefront Granby Escape w/ Private Dock & Kayaks!
3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Living area
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Interior
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Interior
Charming Windsor Home w/ Private Backyard!
3.0 star property
Charming Windsor Home w/ Private Backyard!
Interior
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
3.5 star property
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Interior
Springfield Vacation Rental: 1 Mi to Downtown
3.5 star property
Springfield Vacation Rental: 1 Mi to Downtown
Interior
Family-friendly Avon Home: 10 Mi to Hartford!
3.0 star property
Family-friendly Avon Home: 10 Mi to Hartford!
Interior
Connecticut Vacation Home Rental w/ Private Pool!
3.0 star property
Connecticut Vacation Home Rental w/ Private Pool!
Interior
Lakefront Home: 2 Mi to Air Line State Park Trail!
3.5 star property
Lakefront Home: 2 Mi to Air Line State Park Trail!
Don't see what you're looking for?
See all available properties in Windsor
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.

Other property types in Windsor

Paper towels
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, (2)
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Fridge, microwave, oven, stovetop
A “Wow” Experience
8.0 out of 10, Very Good, (1)
"We had a great stay at this property. Beds were very comfortable, which is not usually the case with many rentals. Good clean and hot showers and towels. Property had everything you need including a BBQ for grilling. My family of 6 was comfortable and plenty of room and space for everyone."
The price is $300
$580 total
includes taxes & fees
May 28 - May 29
A “Wow” Experience
Fridge, microwave, oven, stovetop
Bungalow House - Free Parking - 10 mins to Hartford & Airport
9.0 out of 10, Wonderful, (17)
"We were able to stay @ this location for several days just before the holidays. The space was perfect for the running around we needed to do and was a solid base of operation. The kitchen, bedroom, and bathroom are well-appointed. We did not spend any time in the living room or outside areas. The water pressure in the shower is amazing and I could spend hours there. :) The home is on a busy road at commute times so take the owner's advice and K turn in the driveway to make exiting the home...
The price is $107
$237 total
includes taxes & fees
May 29 - May 30
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.

Windsor Cottages information

Number of reviews
66
Accommodation
24 Cottages
Lowest Price
$209
Highest Price
$209

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start planning for a memorable stay close to nature. If you’re on a budget, click on how much you want to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a hot tub or a kitchen. We’ll help you find the right digs whatever your getaway looks like.
How can I find cheap cottages in Windsor?
With Expedia’s useful filter tool, scoring cheap cottages in Windsor couldn’t be easier. To discover accommodations that’ll make your hip pocket happy, narrow your search by budget, amenities and star rating.
What is there to do in Windsor near my cottage?
Windsor has enough activities and experiences to keep you busy for weeks (or months!), beginning with Xfinity Theatre. Connecticut Science Center, Nomads Adventure Quest and Talcott Mountain State Park are other well-known attractions. If you’re lingering longer, Broad Brook Opera House and Wadsworth Atheneum Museum of Art are worthwhile additions to your itinerary.

Recent reviews of Windsor hotels
Expedia verified reviews