Holiday Homes in Windsor

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Windsor holiday homes

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, (36 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 €246
includes taxes & fees
20 Jan - 21 Jan
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Interior

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12 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 €239
includes taxes & fees
30 Jan - 31 Jan
The Serene Skyway Retreat
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is €260
includes taxes & fees
18 Jan - 19 Jan
Private Apartment in Berlin
Private kitchen

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is €295
includes taxes & fees
25 Jan - 26 Jan
Welcoming 3-bedroom house- Gardner home
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, (5 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 €248
includes taxes & fees
20 Jan - 21 Jan
Modern & Cozy Cape | 4 Bedroom House | Central Location
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 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 €208
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is €189
includes taxes & fees
19 Jan - 20 Jan
Cozy Guest Suite in Historic Home
Smart TV

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
2.0 star property
West Hartford
8.6 out of 10, Excellent, (9 reviews)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is €277
includes taxes & fees
14 Feb - 15 Feb
Charming 3-Bedroom Home with Modern Comforts in West Hartford
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, (15 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is €246
includes taxes & fees
28 Jan - 29 Jan
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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
10.0 out of 10, Exceptional, (4 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is €391
includes taxes & fees
20 Jan - 21 Jan
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
The price is €87
includes taxes & fees
25 Jan - 26 Jan
Entire guest suite in South Windsor, Connecticut
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is €199
includes taxes & fees
25 Jan - 26 Jan
#26 Beautifully Renovated 2 BR Home
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
2.0 star property
Manchester
The price is €335
includes taxes & fees
19 Jan - 20 Jan
Willow Haven 2BR Cozy Retreat, Close to Hartford
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 €302
includes taxes & fees
18 Jan - 19 Jan
Newly Beautiful renovated first floor apartment getaway
Microwave, oven, stovetop, dishwasher

One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.
Rocky Hill
The price is €122
includes taxes & fees
17 Jan - 18 Jan
One private bedroom with work space and shared home with spa.
Exterior detail

Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (1 review)
"Great house. Very spacious. Perfect for friends gathering for a local event. "
United States
Marcy Z.
The price is €658
includes taxes & fees
14 Feb - 15 Feb
Modern Victorian 3BR 2BA Apt with Parking
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
2.0 star property
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 €221
includes taxes & fees
17 Jan - 18 Jan
Sun Filled Lake House Living
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
2.0 star property
Bloomfield
10.0 out of 10, Exceptional, (4 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is €618
includes taxes & fees
18 Jan - 19 Jan
Stylish Townhome | Perfect for Family Gatherings & Events
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, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is €320
includes taxes & fees
18 Jan - 19 Jan
Big farmhouse in the foothills of the Berkshires
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)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
The price is €463
includes taxes & fees
31 Jan - 1 Feb
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
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 Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"The room was drafty around the heating unit. Additionally, this hotel, like most newly built hotels, uses an automatic thermostat for the heat and cool. When the thermostat is set and it gets a little too warm in the room, and you turn it down a couple degrees the AC kicks on rather than just allowing the ambient temp drop. When the outside temp is 18 degrees having the AC running is not a pleasant experience. Overall, this is a really nice place to stay. Staff is friendly and its clean."
Mark 4-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
256
Accommodation
204 Holiday Homes
Lowest Price
€122
Highest Price
€658