Holiday Homes in Windsor

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Windsor holiday homes

Dining

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (11 reviews)
"Everything was seamless - we enjoyed the location close to downtown hartford and six flags. the listing was clean and accurate and the beds were comfortable."
United States
AJ P.
The price is NZ$1,187
includes taxes & fees
25 May - 26 May
Spacious Yard w/ Gazebo: Charming Windsor Retreat
Interior

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (39 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 NZ$593
includes taxes & fees
26 May - 27 May
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
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 NZ$577
includes taxes & fees
18 May - 19 May
#24 *Serenity* A Lakefront Cottage Retreat
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 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 NZ$535
includes taxes & fees
19 May - 20 May
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Exterior

15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed
Manchester
9.2 out of 10, Wonderful, (7 reviews)
"Great location, spacious, comfortable and clean. The host was very responsive and easy to work with, Definitely deserves 5 stars for quality and price."
Singapore
Angelo N.
15mins to Hartford, Home in Manchester w/ King Bed
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 NZ$486
includes taxes & fees
18 May - 19 May
The Serene Skyway Retreat
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (27 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 NZ$389
includes taxes & fees
18 May - 19 May
Family Stays: Middletown, CT
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 NZ$201
includes taxes & fees
26 May - 27 May
Entire guest suite in South Windsor, Connecticut
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
The price is NZ$671
includes taxes & fees
19 May - 20 May
Willow Haven 2BR Cozy Retreat, Close to Hartford
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 NZ$766
includes taxes & fees
14 May - 15 May
Newly Renovated 4 Bedroom House
Smart TV

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (9 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 NZ$496
includes taxes & fees
19 May - 20 May
Modern & Cozy Cape | 4 Bedroom House | Central Location
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 NZ$592
includes taxes & fees
19 May - 20 May
Charming 3-Bedroom Home with Modern Comforts in West Hartford
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
The price is NZ$583
includes taxes & fees
21 May - 22 May
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Combined shower/bathtub, hair dryer, towels, toilet paper

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 NZ$373
includes taxes & fees
24 May - 25 May
Charming 3 bed/2 bath town home with gorgeous back yard
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 NZ$809
includes taxes & fees
14 May - 15 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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 NZ$599
includes taxes & fees
21 May - 22 May
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Interior

#28- *Modern Bungalow*

#28- *Modern Bungalow*
New Britain
8.8 out of 10, Excellent, (3 reviews)
"This stay was very comfortable and also not too fat from the Convention Center either "
United States
Vicente B.
The price is NZ$466
includes taxes & fees
17 May - 18 May
#28- *Modern Bungalow*
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 NZ$1,281
includes taxes & fees
17 May - 18 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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 NZ$553
includes taxes & fees
21 May - 22 May
Newly Beautiful renovated first floor apartment getaway
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
"Excellent hotel. Good value. Excellent location with nice woods in the back with a patio with picnic tables plus they had a grill. The hotel is a little outdated and could use an upgrade, but the room was very comfortable and clean. The breakfast was good and the coffee was great. Met some great people there. Will be staying there again in a few weeks."
Paul 2-night trip
Posted 8 hours ago
Holiday Inn Express Southington by IHG

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
256
Accommodation
217 Holiday Homes
Lowest Price
NZ$201
Highest Price
NZ$1,281