A rustic barn surrounded by autumn foliage and a field.

Search Vacation 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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Windsor vacation homes

A modern living room with a sofa, a coffee table, and a rug.

1. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (12 reviews)
"Very clean and spacious! Would definitely recommend."
United States
Husam
The price is ￥13,678
￥18,896 total
includes taxes & fees
Oct 18 - Oct 19
Entire guest suite in South Windsor, Connecticut
A hotel room with a bed, a nightstand, a lamp, and a wardrobe.

2. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Windsor Locks
The price is ￥12,352
￥14,205 total
includes taxes & fees
Nov 1 - Nov 2
1 Queen Bed | Micfridge
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.

3. 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 stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
The price is ￥39,752
￥83,710 total
includes taxes & fees
Oct 20 - Oct 21
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.

4. 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 ￥22,163
￥48,917 total
includes taxes & fees
Nov 1 - Nov 2
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

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 ￥22,005
￥48,736 total
includes taxes & fees
Oct 13 - Oct 14
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a TV, sofas, armchairs, and a fireplace.

6. 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 ￥17,946
￥74,738 total
includes taxes & fees
Oct 19 - Oct 20
Willow Haven 2BR Cozy Retreat, Close to Hartford
Dining

7. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (25 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 ￥53,857
￥97,430 total
includes taxes & fees
Oct 25 - Oct 26
Prime West Hartford Center: Timeless Charm
A bedroom with a bed, a bedside table, a lamp, and two framed pictures on the wall.

8. Red Door Retreat

Red Door Retreat
Vernon
The price is ￥26,319
￥53,753 total
includes taxes & fees
Oct 13 - Oct 14
Red Door Retreat
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 ￥32,998
￥70,125 total
includes taxes & fees
Oct 13 - Oct 14
The Game House Arcade – West Hartford
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

10. 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 ￥40,692
￥80,154 total
includes taxes & fees
Oct 13 - Oct 14
Charming New England Home in West Hartford Center
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

11. 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 ￥16,939
￥49,526 total
includes taxes & fees
Oct 22 - Oct 23
Sun Filled Lake House Living
A patio area with wicker furniture and a brick floor.

12. 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 traveler
The price is ￥28,496
￥72,099 total
includes taxes & fees
Oct 20 - Oct 21
The Old Avon 1800 Manor
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

13. 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, (11 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 ￥25,361
￥58,413 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

14. 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 ￥39,578
￥71,319 total
includes taxes & fees
Oct 13 - Oct 14
Lakefront Property with Scenic View - All Seasons!
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
The price is ￥28,781
￥36,264 total
includes taxes & fees
Nov 2 - Nov 3
Collinsville River Escape / Fall Foliage, Deck & Yard
A dining area with a round table, four chairs, and a kitchen in the background.

16. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is ￥28,353
￥39,352 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 2-Bedroom Springfield Home 1.5 Baths
A modern kitchen with a central island, wooden bar stools, and recessed lighting.

17. Spacious & Newly Renovated Longmeadow Getaway

Spacious & Newly Renovated Longmeadow Getaway
Longmeadow
6.0 out of 10, (3 reviews)
"Great location. Comfortable beds. Good air conditioning."
United States
Matt K.
The price is ￥64,116
￥105,394 total
includes taxes & fees
Oct 21 - Oct 22
Spacious & Newly Renovated Longmeadow Getaway
An outdoor seating area with a wood-burning stove, a chair, and a view of a lake.

18. Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (30 reviews)
"The lake house was charming, comfortable and well stocked with necessities like towels, blankets, dishes, etc"
United States
Martin G.
Spacious modern home on private lake
A modern living room with a sofa, a coffee table, and a red patterned rug.

19. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (51 reviews)
"House was super clean, coffee was a nice surprise. Comfy beds, quiet street. Super close to the Big E. Thanks Rose!"
United States
Brian
The price is ￥26,359
￥54,331 total
includes taxes & fees
Oct 13 - Oct 14
Cozy & Spacious Entire Home in Springfield
A patio with a table and chairs, a grill, and a view of a lake.

20. 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, (74 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥49,393
￥83,216 total
includes taxes & fees
Oct 19 - Oct 20
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

8/10 Good
"We liked that the room came with a small kitchen-net. That would have been convenient had we stayed longer than a night. The room and bathroom were roomie for two people. Though the room was nice, the room had a musty smell and one trash can had not been empty. Made us wondered how thoroughly clean it was😕"
Michael 2-night trip
Posted 2 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
299
Accommodation
216 Vacation Homes
Lowest Price
￥14,205
Highest Price
￥105,394