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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Windsor holiday homes

A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

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 AU$996
includes taxes & fees
29 Sept - 30 Sept
Spacious Yard w/ Gazebo: Charming Windsor Retreat
A modern living room with a sofa, a coffee table, and a rug.

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is AU$170
includes taxes & fees
29 Sept - 30 Sept
Entire guest suite in South Windsor, Connecticut
A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

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 AU$494
includes taxes & fees
20 Sept - 21 Sept
The Serene Skyway Retreat
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

4. 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 AU$433
includes taxes & fees
21 Sept - 22 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a TV, sofas, armchairs, and a fireplace.

5. 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 AU$651
includes taxes & fees
20 Sept - 21 Sept
Willow Haven 2BR Cozy Retreat, Close to Hartford
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

6. 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 AU$420
includes taxes & fees
20 Sept - 21 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A small house with a red door, white shutters, and a brick chimney.

7. Red Door Retreat

Red Door Retreat
Vernon
The price is AU$402
includes taxes & fees
17 Sept - 18 Sept
Red Door Retreat
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a coffee maker on the table.

8. 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 AU$779
includes taxes & fees
21 Sept - 22 Sept
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

9. 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 AU$503
includes taxes & fees
29 Sept - 30 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

10. 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 AU$756
includes taxes & fees
13 Oct - 14 Oct
Prime West Hartford Center: Timeless Charm
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

11. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
The price is AU$861
includes taxes & fees
22 Sept - 23 Sept
Charming New England Home in West Hartford Center
A living room with a blue sofa, a round coffee table, and a staircase.

12. 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 price is AU$746
includes taxes & fees
20 Sept - 21 Sept
The Game House Arcade – West Hartford
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

13. #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 AU$481
includes taxes & fees
20 Sept - 21 Sept
#24 Serenity A Lakefront Cottage Retreat
A covered patio with a dining table, chairs, and a grill.

14. 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
The price is AU$995
includes taxes & fees
4 Oct - 5 Oct
Prime West Hartford Center Location: Historic Gem
A spacious kitchen with a large island, wooden beams, and pendant lighting.

15. 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 AU$534
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

16. 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 AU$420
includes taxes & fees
5 Oct - 6 Oct
Sun Filled Lake House Living
A patio area with wicker furniture and a brick floor.

17. 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 AU$646
includes taxes & fees
23 Sept - 24 Sept
The Old Avon 1800 Manor
A modern living room with a white sofa, a coffee table, and a red and black rug. There is a staircase with a white railing leading to a second floor.

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 AU$482
includes taxes & fees
21 Sept - 22 Sept
Cozy & Spacious Entire Home in Springfield
A modern living room with two sofas, a glass coffee table, and a decorative cake.

19. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AU$361
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-Bedroom Springfield Home 1.5 Baths
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

20. 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 AU$538
includes taxes & fees
17 Sept - 18 Sept
Beautifully 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

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

10/10 Excellent
"So so"
Scarleth 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
14,450
Accommodation
209 Holiday Homes
Lowest Price
AU$112
Highest Price
AU$337