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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for South Windsor holiday homes

Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is £91
includes taxes & fees
28 Apr - 29 Apr
Entire guest suite in South Windsor, Connecticut
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.4 out of 10, Exceptional, (20 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is £242
includes taxes & fees
28 Apr - 29 Apr
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Interior

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (38 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is £187
includes taxes & fees
28 Apr - 29 Apr
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Fridge, microwave, oven, stovetop

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is £311
includes taxes & fees
28 Apr - 29 Apr
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (22 reviews)
"Great place"
United States
John S.
The price is £236
includes taxes & fees
28 Apr - 29 Apr
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (13 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is £207
includes taxes & fees
5 May - 6 May
The Serene Skyway Retreat
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (22 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is £309
includes taxes & fees
19 May - 20 May
#24 *Serenity* A Lakefront Cottage Retreat
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (8 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is £228
includes taxes & fees
12 May - 13 May
Modern & Cozy Cape | 4 Bedroom House | Central Location
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
7.6 out of 10, Good, (4 reviews)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is £459
includes taxes & fees
28 Apr - 29 Apr
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Smart TV

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
West Hartford
7.8 out of 10, Good, (11 reviews)
"everything was good but there was a few things that needed fix up on I contacted the host and let them know about a few things and so on other then that i enjoyed my stay "
United States
Shaheym J.
The price is £193
includes taxes & fees
28 Apr - 29 Apr
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (25 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is £185
includes taxes & fees
18 May - 19 May
Family Stays: Middletown, CT
Smart TV

Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
8.8 out of 10, Excellent, (3 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is £232
includes taxes & fees
28 Apr - 29 Apr
Newly Beautiful renovated first floor apartment getaway
Fridge, microwave, stovetop, dishwasher

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (5 reviews)
"The house was perfect for a weekend wedding trip. "
United States
Liane V.
The price is £339
includes taxes & fees
13 May - 14 May
Newly Renovated 4 Bedroom House
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (64 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is £388
includes taxes & fees
14 May - 15 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

Charming 3 bed/2 bath town home with gorgeous back yard

Charming 3 bed/2 bath town home with gorgeous back yard
Forest Park
9.8 out of 10, Exceptional, (13 reviews)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
United States
Barbara W.
The price is £186
includes taxes & fees
24 May - 25 May
Charming 3 bed/2 bath town home with gorgeous back yard
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is £295
includes taxes & fees
3 May - 4 May
Willow Haven 2BR Cozy Retreat, Close to Hartford
Living area

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Sixteen Acres
8.8 out of 10, Excellent, (5 reviews)
"Great place to stay. It was clean and organized. Our family enjoyed this location, what it had to provide, and the host was great. "
United States
Diana P.
The price is £269
includes taxes & fees
4 May - 5 May
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is £369
includes taxes & fees
28 Apr - 29 Apr
Cozy basement apartment with private bathroom, kitchen and entrance.
Fridge, microwave, oven, stovetop

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
9.6 out of 10, Exceptional, (5 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is £302
includes taxes & fees
28 Apr - 29 Apr
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Smart TV, fireplace, video games, books

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (37 reviews)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is £254
includes taxes & fees
28 Apr - 29 Apr
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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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Top South Windsor Hotel Reviews

Quality Inn West Springfield

Quality Inn West Springfield

2/10 Terrible
"I feel like the picture has nothing to do with the place. The place was nothing like the picture but when you need something last minute, it is what it is."
Latasha 2-night trip
Posted 3 hours ago
Quality Inn West Springfield

Find out more about South Windsor

South Windsor Holiday Homes information

Number of reviews
255
Accommodation
221 Holiday Homes
Lowest Price
£91
Highest Price
£459