Windsor, CT Vacation Homes from ￥20,650

A rustic barn surrounded by autumn foliage and a field.

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Our top choices for Windsor vacation homes

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Windsor

Delores N.

￥115,285 total

includes taxes & fees

Sep 1 - Sep 2

2. Entire guest suite in South Windsor, Connecticut

South Windsor

Arthur

￥20,650 total

includes taxes & fees

Sep 8 - Sep 9

3. The Serene Skyway Retreat

Windsor Locks

Michael P.

￥56,487 total

includes taxes & fees

Aug 30 - Aug 31

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

Manchester

alissa

￥66,828 total

includes taxes & fees

Aug 30 - Aug 31

5. Modern & Cozy Cape | 4 Bedroom House | Central Location

Manchester Center

John S.

￥47,362 total

includes taxes & fees

Sep 14 - Sep 15

6. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

Matthew R.

￥83,344 total

includes taxes & fees

Sep 8 - Sep 9

7. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Manchester

John S.

￥50,522 total

includes taxes & fees

Sep 20 - Sep 21

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

Manchester

Kim A.

￥51,318 total

includes taxes & fees

Aug 30 - Aug 31

9. Prime West Hartford Center: Timeless Charm

West Hartford

Michael W.

￥86,659 total

includes taxes & fees

Sep 14 - Sep 15

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

West Suffield

Wendy C.

￥63,955 total

includes taxes & fees

Sep 13 - Sep 14

11. Sun Filled Lake House Living

Avon

Joseph C.

￥48,544 total

includes taxes & fees

Sep 9 - Sep 10

12. The Game House Arcade – West Hartford

West Hartford

Mike W.

￥85,284 total

includes taxes & fees

Aug 30 - Aug 31

13. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Somers

"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...

Jenny

￥55,623 total

includes taxes & fees

Sep 8 - Sep 9

14. The Old Avon 1800 Manor

Avon

Anonymous traveler

￥74,970 total

includes taxes & fees

Sep 1 - Sep 2

15. Charming New England Home in West Hartford Center

West Hartford

karen

￥95,326 total

includes taxes & fees

Aug 30 - Aug 31

16. Beautifully Renovated First-Floor Apartment Getaway

Forest Park

Alyssa A.

￥54,962 total

includes taxes & fees

Sep 7 - Sep 8

17. Spacious & Newly Renovated Longmeadow Getaway

Longmeadow

Matt K.

￥74,776 total

includes taxes & fees

Aug 28 - Aug 29

18. Cozy & Spacious Entire Home in Springfield

Forest Park

Lorrie

￥54,999 total

includes taxes & fees

Sep 7 - Sep 8

19. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

￥78,165 total

includes taxes & fees

Sep 10 - Sep 11

20. 1 Min to I-91 - Newly Renovated Modern 2 BR Home

Berlin

"This property is absolutely beautiful and well maintained. We stayed for three weeks with no problems or issues. Everything was clean and the kitchen has plenty of dishes, silverware, pots and pans. The dishwasher was a bonus making clean up easy and the grill was great allowing us to grill many meals. The owner was not only quick to respond but very helpful. Pet friendly was great for us so our medium size dog could travel with us. Excellent location in central CT with many stores and...

Diane W.

￥73,167 total

includes taxes & fees

Sep 6 - Sep 7

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Top Windsor Hotel Reviews

Ramada by Wyndham Hartford North / Bradley Airport

8/10 Good

"When we stayed, they were transitioning to new management. Someone"

Motel 6 Enfield, CT - Hartford

10/10 Excellent

"I was pleasantly surprised by the cleanliness and price point for a room with a comfortable king-sized bed, modernized bathroom, and relatively quiet air-conditioning unit. Although the room lacked a clock, refrigerator, microwave, and radio, it was perfect for an overnight where no extras were required. There was even a 24-hour manned check-in/out desk."

Best Western Hartford Hotel & Suites

8/10 Good

"The facilities amenities offer as the whirlpool was out of order, dryer in laundry room is out of order and the bathroom toilet bowl loose with a foul sewer smell at times. The bathtub very slippery no lower hand-bars for people with disabilities or elderly. The room was nice and spacious but too much humidity in the room with some mold stain on the ceiling. No USB outlets and outlet for charging computer, phones and etc. The staff were friendly and helpful. Overall rate a 9 out of 10."

HYATT house Hartford North/Windsor

10/10 Excellent

"Travelled with family, 2 teenagers and 2 younger kids for one night. We were treated with a very sincere and kind “welcome” from the receptionist. She was very efficient and friendly. The property and lobby were spotless and clean. We stayed in the 1 bedroom , double bed suite that was very spacious. It had a small kitchen area and was equipped with kitchen appliances. Very comfortable beds not so comfortable pull out couch. Pool water was chilly but area was clean with the exception of the hot tub. Although it was very warm and comfortable, it seemed to need some attention to the paint and walls surrounding it. We enjoyed the free breakfast of pancakes, scrambled eggs, sausages, home fries. Also variety of cereal, yogurt, fruit, juices, coffee, tea, and breads. I always enjoy Hyatt House and definitely will stay again."

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews	324
Accommodation	226 Vacation Homes
Lowest Price	￥20,650
Highest Price	￥115,285

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation homes

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

2. Entire guest suite in South Windsor, Connecticut

3. The Serene Skyway Retreat

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

5. Modern & Cozy Cape | 4 Bedroom House | Central Location

6. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

7. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

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

9. Prime West Hartford Center: Timeless Charm

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

11. Sun Filled Lake House Living

12. The Game House Arcade – West Hartford

13. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

14. The Old Avon 1800 Manor

15. Charming New England Home in West Hartford Center

16. Beautifully Renovated First-Floor Apartment Getaway

17. Spacious & Newly Renovated Longmeadow Getaway

18. Cozy & Spacious Entire Home in Springfield

19. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

20. 1 Min to I-91 - Newly Renovated Modern 2 BR Home

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Ramada by Wyndham Hartford North / Bradley Airport

Holiday Inn Express Springfield Downtown by IHG

The Capitol Hotel

Motel 6 Enfield, CT - Hartford

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Best Western Hartford Hotel & Suites

MGM Springfield

Holiday Inn Express Southington by IHG

HYATT house Hartford North/Windsor

Find out more about Windsor

Windsor Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Windsor

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation homes

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

2. Entire guest suite in South Windsor, Connecticut

3. The Serene Skyway Retreat

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

5. Modern & Cozy Cape | 4 Bedroom House | Central Location

6. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

7. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

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

9. Prime West Hartford Center: Timeless Charm

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

11. Sun Filled Lake House Living

12. The Game House Arcade – West Hartford

13. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

14. The Old Avon 1800 Manor

15. Charming New England Home in West Hartford Center

16. Beautifully Renovated First-Floor Apartment Getaway

17. Spacious & Newly Renovated Longmeadow Getaway

18. Cozy & Spacious Entire Home in Springfield

19. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

20. 1 Min to I-91 - Newly Renovated Modern 2 BR Home

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Ramada by Wyndham Hartford North / Bradley Airport

Find out more about Windsor

Windsor Vacation Homes information

Explore a world of travel with Expedia