A rustic barn surrounded by autumn foliage and a field.

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Windsor holiday homes

Dining

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 reviews)
"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."
United States
Delores N.
The price is €633
includes taxes & fees
14 Sept - 15 Sept
Spacious Yard w/ Gazebo: Charming Windsor Retreat
Smart TV

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (9 reviews)
"Good location"
United States
Arthur
The price is €116
includes taxes & fees
28 Sept - 29 Sept
Entire guest suite in South Windsor, Connecticut
Smart TV, fireplace

3. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is €299
includes taxes & fees
20 Sept - 21 Sept
The Serene Skyway Retreat
TV, fireplace

4. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is €381
includes taxes & fees
14 Sept - 15 Sept
Willow Haven 2BR Cozy Retreat, Close to Hartford
Interior

5. 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 €262
includes taxes & fees
14 Sept - 15 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Coffee/tea maker, fridge, microwave, oven

6. 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, (11 reviews)
"Great stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
The price is €472
includes taxes & fees
16 Sept - 17 Sept
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Smart TV

7. 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, (30 reviews)
"Was a great stay"
United States
John S.
The price is €273
includes taxes & fees
20 Sept - 21 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Exterior

8. Red Door Retreat

Red Door Retreat
Vernon
The price is €263
includes taxes & fees
14 Sept - 15 Sept
Red Door Retreat
Dining

9. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is €429
includes taxes & fees
30 Sept - 1 Oct
Prime West Hartford Center: Timeless Charm
Interior

10. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is €362
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
TV, books

11. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The Game House Arcade – West Hartford
Property grounds

12. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 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 €266
includes taxes & fees
28 Sept - 29 Sept
Sun Filled Lake House Living
Outdoor dining

13. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (35 reviews)
"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."
United States
Trish
Prime West Hartford Center Location: Historic Gem
2 bedrooms, iron/ironing board, WiFi, bed sheets

14. 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
9.6 out of 10, Exceptional, (9 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 €310
includes taxes & fees
15 Sept - 16 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Terrace/patio

15. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is €404
includes taxes & fees
23 Sept - 24 Sept
The Old Avon 1800 Manor
Outdoor dining

16. 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, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is €459
includes taxes & fees
20 Sept - 21 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds

17. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is €350
includes taxes & fees
28 Sept - 29 Sept
#24 Serenity A Lakefront Cottage Retreat
Smart TV, fireplace, video games, books

18. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (46 reviews)
"It was nice stay!"
United States
Lorrie
The price is €316
includes taxes & fees
14 Sept - 15 Sept
Cozy & Spacious Entire Home in Springfield
Smart TV

19. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.2 out of 10, Wonderful, (5 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 €334
includes taxes & fees
14 Sept - 15 Sept
Beautifully Renovated First-Floor Apartment Getaway
Exterior

20. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is €219
includes taxes & fees
14 Oct - 15 Oct
Family Stays: Middletown, CT
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

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

8/10 Good
"For the price margin and star rating - I was very pleased with my stay. The bed was very comfortable. The room clean and with decent furniture. The bathroom had a updated sliding glass door for shower. I decided to eat breakfast next door because of the rating of the diner, but they did offer breakfast as well. I would stay there again."
Craig 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
309
Accommodation
226 Holiday Homes
Lowest Price
€116
Highest Price
€633