Old tobacco barn with oak trees

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 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 €310
includes taxes & fees
16 Jun - 17 Jun
#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 €296
includes taxes & fees
16 Jun - 17 Jun
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, (2 reviews)
"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 €117
includes taxes & fees
13 Jul - 14 Jul
Entire guest suite in South Windsor, Connecticut
Terrace/patio

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 €277
includes taxes & fees
16 Jun - 17 Jun
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (14 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 €268
includes taxes & fees
15 Jun - 16 Jun
The Serene Skyway Retreat
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 €351
includes taxes & fees
16 Jun - 17 Jun
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
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 €256
includes taxes & fees
16 Jun - 17 Jun
Modern & Cozy Cape | 4 Bedroom House | Central Location
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 €277
includes taxes & fees
16 Jun - 17 Jun
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Hair dryer

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is €387
includes taxes & fees
21 Jun - 22 Jun
Willow Haven 2BR Cozy Retreat, Close to Hartford
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 €765
includes taxes & fees
13 Jul - 14 Jul
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
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 €302
includes taxes & fees
17 Jun - 18 Jun
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 €237
includes taxes & fees
21 Jun - 22 Jun
Luxe Lady Executive & Family Retreat | 1 Bedroom Townhouse
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 €405
includes taxes & fees
15 Jun - 16 Jun
Newly Renovated 4 Bedroom House
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.
#26 Beautifully Renovated 2 BR Home
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is €281
includes taxes & fees
20 Jun - 21 Jun
Sun Filled Lake House Living
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 €249
includes taxes & fees
6 Jul - 7 Jul
Family Stays: Middletown, CT
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, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is €512
includes taxes & fees
20 Jun - 21 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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 €302
includes taxes & fees
22 Jun - 23 Jun
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
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 €287
includes taxes & fees
14 Jun - 15 Jun
Newly Beautiful renovated first floor apartment getaway
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 €214
includes taxes & fees
18 Jun - 19 Jun
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

Economy Inn

Economy Inn

6/10 Okay
"We left a party early so we could watch the NBA Finals ... The TV only picked up 2 channels ... no local channels, so we couldn't watch the game. Very, very disappointed ... I've never seen a hotel in a large city which did not offer any local channels, and only 2 channels, each of which I would never watch ... very disappointed ..."
Carol 1-night trip
Posted 2 hours ago
Economy Inn

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
383
Accommodation
232 Holiday Homes
Lowest Price
€117
Highest Price
€765