A rustic barn surrounded by autumn foliage and a field.

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for 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, (6 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 HK$677
HK$936 total
includes taxes & fees
23 Jul - 24 Jul
Entire guest suite in South Windsor, Connecticut
Interior

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (43 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 HK$1,583
HK$3,044 total
includes taxes & fees
5 Aug - 6 Aug
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.2 out of 10, Wonderful, (15 reviews)
"We loved the home. "
United States
Karen D.
The price is HK$800
HK$2,397 total
includes taxes & fees
19 Jul - 20 Jul
The Serene Skyway Retreat
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, (148 reviews)
"Great location"
United States
Will G.
The price is HK$1,489
HK$2,784 total
includes taxes & fees
27 Jul - 28 Jul
Big farmhouse in the foothills of the Berkshires
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is HK$1,543
HK$3,084 total
includes taxes & fees
22 Jul - 23 Jul
#24 *Serenity* A Lakefront Cottage Retreat
Interior

Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Everything was spectacular from the check in process to the personal experiences."
United States
leigh
The price is HK$1,514
HK$3,033 total
includes taxes & fees
5 Aug - 6 Aug
Linny's - Lakefront Retreat Private Dock & Firepit
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 HK$1,215
HK$2,573 total
includes taxes & fees
22 Jul - 23 Jul
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
9.2 out of 10, Wonderful, (25 reviews)
"Was a great stay"
United States
John S.
The price is HK$1,254
HK$2,626 total
includes taxes & fees
22 Jul - 23 Jul
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to 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
10.0 out of 10, Exceptional, (5 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is HK$1,432
HK$2,870 total
includes taxes & fees
22 Jul - 23 Jul
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Smart TV

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

15mins to Hartford, Home in Manchester w/ King Bed
Manchester
8.4 out of 10, Very good, (8 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
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 HK$800
HK$2,397 total
includes taxes & fees
30 Jul - 31 Jul
Sun Filled Lake House Living
Smart TV

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
West Hartford
7.6 out of 10, Good, (12 reviews)
"The owner was missing during check-in time. Ended up in a hotel with two rooms and spent double. VRBO has yet to reimburse the thousands of additional dollars spent."
United States
tony
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Smart TV, fireplace, video games, books

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

Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (44 reviews)
"It was nice stay!"
United States
Lorrie
The price is HK$1,411
HK$2,819 total
includes taxes & fees
22 Jul - 23 Jul
Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
TV, fireplace

Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (1 review)
"House was clean and very good communication with owners. I put 4 stars only because there was only one television which some families might not mind but was t a deal breaker we bought one and made it work. Also only window unit which is not shown in the photos so it was really cold in the front of the home vs. bedrooms but again not a deal breaker. Beautiful nature outside rabbits woodchuck birds raccoon & skunk!!! very convenient location close to grocery not far from restaurants, etc."
United States
Dionne V.
The price is HK$837
HK$3,262 total
includes taxes & fees
23 Jul - 24 Jul
Willow Haven 2BR Cozy Retreat, Close to Hartford
Coffee/tea maker, fridge, microwave, oven

#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, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is HK$1,921
HK$4,004 total
includes taxes & fees
28 Jul - 29 Jul
#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, (29 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is HK$1,254
HK$2,203 total
includes taxes & fees
10 Aug - 11 Aug
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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,445
HK$4,120 total
includes taxes & fees
13 Aug - 14 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Interior

Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is HK$1,305
HK$3,915 total
includes taxes & fees
22 Jul - 23 Jul
Cozy basement apartment with private bathroom, kitchen and entrance.
Coffee/tea maker, fridge, microwave, oven

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, (9 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is HK$1,834
HK$3,952 total
includes taxes & fees
5 Aug - 6 Aug
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
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

Quality Inn West Springfield

Quality Inn West Springfield

8/10 Good
"In Room 410 the sliding glass door is out of square therefore there is a gap 1-2 inches from top of door to the floor. Highway noise, bugs, heat and humidity is continuously enter the room. When I went out for the day the AC pauses so when I came back my clothes felt damp from humidity buildup. WiFi was not good in my room. Breakfast was better than expected. Staff was great."
Daniel 7-night trip
Posted less than an hour ago
Quality Inn West Springfield

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
458
Accommodation
220 Vacation Homes
Lowest Price
HK$936
Highest Price
HK$4,120

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