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Check prices for these dates

Next weekend
25 Jul - 27 Jul
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15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Windsor

Charming Cottage by the Lake❤️
Outdoor dining

Charming Cottage by the Lake❤️

9.8 out of 10, Exceptional, (14)
"My friends and I had a very lovely weekend. The cottage is well equipped, well maintained, very clean. I loved being able to bring my doggie with me. "
Charming Cottage by the Lake❤️
Lakefront Connecticut Retreat Near UConn
Fridge, microwave, stovetop, dishwasher

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (21)
"The house is beautiful and had everything we needed for the weekend. Since it was cooler and a bit rainy we only availed ourselves to the outside table for peaceful and quiet times. Our NYC family really enjoyed the quiet! We will be looking at this house in our future visits. "
Lakefront Connecticut Retreat Near UConn
Lakefront Tranquility/Fishermans Delight
Interior

Lakefront Tranquility/Fishermans Delight

9.8 out of 10, Exceptional, (19)
"Great cabin very relaxing"
Lakefront Tranquility/Fishermans Delight
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Exterior

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
Property grounds

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"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
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Interior

Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.

2.0 star property
9.6 out of 10, Exceptional, (4)
"Host were super friendly and very communicative"
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Lake Getaway at Coventry Lake! close to Uconn
Exterior

Lake Getaway at Coventry Lake! close to Uconn

10.0 out of 10, Exceptional, (19)
"Nice spot, close to campus and perfect size."
Lake Getaway at Coventry Lake! close to Uconn
Lakefront Connecticut Retreat Near Uconn
Cottage (2 Bedrooms) | Interior

Lakefront Connecticut Retreat Near Uconn

3.0 star property
Lakefront Connecticut Retreat Near Uconn
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
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!
Reel Simple on Bolton Lake
Outdoor dining

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (24)
"We stayed here while visiting our family during a stressful time. It was wonderful to come back to this cozy quiet cottage each night."
Reel Simple on Bolton Lake
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard

10.0 out of 10, Exceptional, (1)
"Nice to have a Vrbo versus hotel in a quiet neighborhood. Heater wasn’t working and owner had someone there within a hour to fix it. We left our laptop and owner notified us immediately. Placed worked out great for our business trip."
Charming 2-bedroom cottage in fantastic Longmeadow with AC, WiFi & fenced yard
Lakefront Cottage w/ Covered Porch & Dock!
Terrace/patio

Lakefront Cottage w/ Covered Porch & Dock!

10.0 out of 10, Exceptional, (15)
"Wonderful stay"
Lakefront Cottage w/ Covered Porch & Dock!
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, (44)
"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!
Lakefront Cottage w/ Covered Porch & Dock!
Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Interior

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Property grounds

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

Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
7 Mi to Forest Park: Springfield Home w/ Yard
Interior

7 Mi to Forest Park: Springfield Home w/ Yard

3.0 star property
7 Mi to Forest Park: Springfield Home w/ Yard
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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Frequently asked questions

Why book your cottage in Windsor with Expedia?
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