Old tobacco barn with oak trees

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
3 July - 5 July
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Windsor holiday homes

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 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 AU$499
includes taxes & fees
17 June - 18 June
#24 *Serenity* A Lakefront Cottage Retreat
Interior

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 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 AU$461
includes taxes & fees
24 June - 25 June
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (4 reviews)
"I had a great one night stay. Place was super clean and fresh. If I’m ever in the area I’ll stay there again for sure. It was a pleasure."
United States
debo9412
The price is AU$187
includes taxes & fees
7 July - 8 July
Entire guest suite in South Windsor, Connecticut
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)
"Was a great stay"
United States
John S.
The price is AU$453
includes taxes & fees
29 June - 30 June
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Interior

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is AU$447
includes taxes & fees
23 June - 24 June
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is AU$450
includes taxes & fees
30 June - 1 July
Modern & Cozy Cape | 4 Bedroom House | Central Location
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
9.8 out of 10, Exceptional, (7 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is AU$612
includes taxes & fees
17 June - 18 June
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is AU$585
includes taxes & fees
23 June - 24 June
Willow Haven 2BR Cozy Retreat, Close to Hartford
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (14 reviews)
"We loved the home. "
United States
Karen D.
The price is AU$424
includes taxes & fees
23 June - 24 June
The Serene Skyway Retreat
Smart TV, offices

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is AU$297
includes taxes & fees
17 June - 18 June
Crested One Place - with Free Parking, Heat & AC
Fridge, microwave, stovetop, dishwasher

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (5 reviews)
"Had a great experience. The house feels like a home, and we enjoyed our stay. Thanks very much. "
United States
Seth G.
The price is AU$642
includes taxes & fees
28 June - 29 June
Newly Renovated 4 Bedroom House
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AU$498
includes taxes & fees
17 June - 18 June
Big farmhouse in the foothills of the Berkshires
Dining

Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse

Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse
Vernon
The price is AU$382
includes taxes & fees
20 June - 21 June
Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse
Fridge, microwave, oven, stovetop

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is AU$839
includes taxes & fees
24 June - 25 June
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (28 reviews)
"House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!"
United States
Diana C.
The price is AU$461
includes taxes & fees
6 July - 7 July
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 AU$477
includes taxes & fees
23 June - 24 June
Newly Beautiful renovated first floor apartment getaway
2 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
10.0 out of 10, Exceptional, (1 review)
"This place was perfect for our needs! It was about 5 minutes from the event we came for which was great. Seeing it was a new listing without any reviews I was slightly skeptical but traveling with a 5 year old, a hotel is always a struggle. This place was everything it was advertised and then some. Absolutely spacious, nicely decorated and plenty plenty plenty of little extras like snacks, toiletries, and a very nice and accommodating host! The furniture was all comfortable and good quality,...
United States
Colleen S.
The price is AU$497
includes taxes & fees
22 June - 23 June
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is AU$693
includes taxes & fees
17 June - 18 June
Cozy basement apartment with private bathroom, kitchen and entrance.
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is AU$405
includes taxes & fees
21 June - 22 June
#26 Beautifully Renovated 2 BR Home
TV

Safe & Quiet 3BR Cape: Sunroom Office + Yard

Safe & Quiet 3BR Cape: Sunroom Office + Yard
East Forest Park
10.0 out of 10, Exceptional, (1 review)
"Very clean and spacious in a very quite residential neighborhood Will go back it was perfect for our visit"
United States
Jackie C.
The price is AU$349
includes taxes & fees
23 June - 24 June
Safe & Quiet 3BR Cape: Sunroom Office + 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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Top Windsor Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent
"Todo de show"
Roberto 3-night trip
Posted 8 hours ago
Holiday Inn Express Springfield Downtown by IHG

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
15,736
Accommodation
227 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$428