A rustic barn surrounded by autumn foliage and a field.

Holiday Homes in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday homes

A two-story house with a red front door, stone steps, and two deer statues.

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (13 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$959
includes taxes & fees
23 Nov - 24 Nov
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
10.0 out of 10, Exceptional, (12 reviews)
"Good location"
United States
Arthur
The price is AU$160
includes taxes & fees
3 Nov - 4 Nov
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, (18 reviews)
"Very clean, the host was very responsive in a timely manner. The location was a nice suburban neighborhood, huge yard, on the end of a cul-de-sac. The kids loved the pool table & downstairs apartment. There are lots of stairs so maybe not the best for an older person, but they did have a ramp entry into the house. The house was very nicely decorated and comfortable furnishings."
United States
Jeanne J.
The price is AU$405
includes taxes & fees
30 Nov - 1 Dec
The Serene Skyway 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.

4. 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, (12 reviews)
"Great location for our six flags visit (about 15 minutes away)."
United States
Stacey B.
The price is AU$641
includes taxes & fees
15 Nov - 16 Nov
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

5. 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, (31 reviews)
"Was a great stay"
United States
John S.
The price is AU$418
includes taxes & fees
1 Nov - 2 Nov
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A modern dining area with a marble table, white chairs, and a chandelier.

6. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is AU$418
includes taxes & fees
1 Nov - 2 Nov
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Dining

7. Prime West Hartford Center | Timeless Charm

Prime West Hartford Center | Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (27 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$666
includes taxes & fees
1 Nov - 2 Nov
Prime West Hartford Center | Timeless Charm
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

8. 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$416
includes taxes & fees
1 Nov - 2 Nov
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a blue sofa, a round coffee table, and a staircase.

9. 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$563
includes taxes & fees
1 Nov - 2 Nov
The Game House Arcade | West Hartford
A modern living room with a grey sectional sofa, a coffee table, decorative mirrors, and a flat-screen TV mounted on the wall.

10. Red Door Retreat

Red Door Retreat
Vernon
The price is AU$501
includes taxes & fees
3 Nov - 4 Nov
Red Door Retreat
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$632
includes taxes & fees
1 Nov - 2 Nov
Charming New England Home in West Hartford Center
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

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 AU$357
includes taxes & fees
17 Nov - 18 Nov
Sun Filled Lake House Living
A covered patio with a dining table, chairs, and a grill.

13. Prime West Hartford Center Location | Historic Gem

Prime West Hartford Center Location | Historic Gem
West Hartford
10.0 out of 10, Exceptional, (37 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$1,062
includes taxes & fees
23 Nov - 24 Nov
Prime West Hartford Center Location | Historic Gem
A patio area with wicker furniture and a brick floor.

14. 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$610
includes taxes & fees
4 Nov - 5 Nov
The Old Avon 1800 Manor
A white building with a porch and a stone border.

15. 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
9.8 out of 10, Exceptional, (12 reviews)
"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"
United States
John
The price is AU$470
includes taxes & fees
2 Nov - 3 Nov
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A wooden deck with a railing, overlooking a calm lake with autumn foliage.

16. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (26 reviews)
"It was great "
United States
Rodrigo C.
#24 *Serenity* A Lakefront Cottage Retreat
A modern kitchen with stainless steel appliances, a wooden dining table, and a ceiling fan.

17. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
The price is AU$462
includes taxes & fees
2 Nov - 3 Nov
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
Property grounds

18. Lakefront Property with Scenic View - All Seasons!

Lakefront Property with Scenic View - All Seasons!
Enfield
10.0 out of 10, Exceptional, (2 reviews)
"My family and I stayed in this lovely cottage the night before our son’s graduation from UConn (approx 49 mins from campus). It was very clean, in a quiet neighborhood and perfect for our needs. Communication with the host was great. We look forward to staying here again in the future."
United States
Diana M.
The price is AU$608
includes taxes & fees
3 Nov - 4 Nov
Lakefront Property with Scenic View - All Seasons!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

19. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AU$342
includes taxes & fees
3 Nov - 4 Nov
Cozy 2-Bedroom Springfield Home 1.5 Baths
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

20. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.4 out of 10, Exceptional, (3 reviews)
"This was a great weekend away in CT! The house was comfortable and clean. Very cozy setup and good communication with the host. The weather wasn’t amazing but we still enjoyed our stay for the weekend."
United States
Brandon R.
The price is AU$287
includes taxes & fees
4 Nov - 5 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"While the hotel is not flashy or modern by any standard, the room I got was clean. And when I opened the curtains - I had a view of the Connecticut State Capitol & Bushnell Park. So it's a great location. I used their underground parking and found the staff to be very helpful. I was in town for a concert - but I could see this as a very handy location for anyone with business in Downtown Hartford."
Theodore 1-night trip
Posted less than an hour ago
The Capitol Hotel

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
242
Accommodation
222 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$1,062