Search Cottages in South 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
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sep - 7 Sep

Cottages in South Windsor

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.8 out of 10, Exceptional, (13)
"Just a nice lake house!!"
The price is SAR 563
SAR 1,302 total
includes taxes & fees
31 Jul - 1 Aug
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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, (20)
"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
Go Jump in the Lake!

Go Jump in the Lake!

10.0 out of 10, Exceptional, (141)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Dining

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!
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!
Cozy 3 bd Cottage w/ access to private lake
Fridge, microwave, dishwasher, toaster

Cozy 3 bd Cottage w/ access to private lake

10.0 out of 10, Exceptional, (2)
"Beautiful place and excellent house."
Cozy 3 bd Cottage w/ access to private lake
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!
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!
Breathtaking Private, Lakefront Retreat.
Property grounds

Breathtaking Private, Lakefront Retreat.

Breathtaking Private, Lakefront Retreat.
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!
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.
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 South Windsor with Expedia?
Expedia has some excellent cottages in South Windsor, so get ready for a memorable vacation close to nature. If you have a set budget, click on how much you want to spend and your preferred property star rating. Or, use our handy filters to search for cottages with a pool or a hot tub. We'll help you find the perfect pad whatever your plans or style of travel.
How can I find cheap cottages in South Windsor?
A great way to find cheap cottages in South Windsor is with Expedia's useful filter tool. Fine-tune your search results by budget, amenities and star rating to access unbeatable bargains in a few clicks.