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Our top choices for South Windsor vacation homes

1. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is ¥13,694
¥17,650 total
includes taxes & fees
Nov 16 - Nov 17
Entire guest suite in South Windsor, Connecticut

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

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
6.8 out of 10, (3 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 ¥20,049
¥74,181 total
includes taxes & fees
Nov 6 - Nov 7
Willow Haven 2BR Cozy Retreat, Close to Hartford

3. 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 ¥26,151
¥51,628 total
includes taxes & fees
Nov 22 - Nov 23
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

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 ¥22,030
¥44,987 total
includes taxes & fees
Nov 8 - Nov 9
Modern & Cozy Cape | 4 Bedroom House | Central Location

5. Red Door Retreat

Red Door Retreat
Vernon
The price is ¥29,955
¥56,534 total
includes taxes & fees
Nov 16 - Nov 17
Red Door Retreat

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, (31 reviews)
"Was a great stay"
United States
John S.
The price is ¥22,189
¥46,755 total
includes taxes & fees
Nov 8 - Nov 9
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

7. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (18 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is ¥14,106
¥43,902 total
includes taxes & fees
Nov 30 - Dec 1
The Serene Skyway Retreat

8. 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 ¥47,705
¥113,573 total
includes taxes & fees
Nov 23 - Nov 24
Spacious Yard w/ Gazebo: Charming Windsor Retreat

9. 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 ¥29,812
¥67,726 total
includes taxes & fees
Nov 15 - Nov 16
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

10. 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 ¥24,962
¥55,452 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

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 price is ¥30,073
¥63,538 total
includes taxes & fees
Nov 5 - Nov 6
The Game House Arcade | West Hartford

12. 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 ¥39,187
¥74,928 total
includes taxes & fees
Nov 9 - Nov 10
Prime West Hartford Center | Timeless Charm

13. 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 ¥10,777
¥39,705 total
includes taxes & fees
Nov 16 - Nov 17
Sun Filled Lake House Living

14. 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 ¥45,930
¥80,506 total
includes taxes & fees
Nov 11 - Nov 12
Charming New England Home in West Hartford Center

15. 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 ¥39,623
¥68,072 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Property with Scenic View - All Seasons!

16. 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 ¥60,329
¥97,974 total
includes taxes & fees
Nov 8 - Nov 9
Prime West Hartford Center Location | Historic Gem

17. Saint James Manor - Sleeps 24 in Style & Comfort with Parking

Saint James Manor - Sleeps 24 in Style & Comfort with Parking
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"Our team was traveling together, it was great to have plenty of beds and lots of space in close proximity to Springfield College."
United States
Zachary R.
The price is ¥149,462
¥257,311 total
includes taxes & fees
Nov 9 - Nov 10
Saint James Manor - Sleeps 24 in Style & Comfort with Parking

18. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.6 out of 10, Exceptional, (7 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 ¥26,289
¥51,501 total
includes taxes & fees
Nov 9 - Nov 10
Beautifully Renovated First-Floor Apartment Getaway

19. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is ¥23,774
¥42,793 total
includes taxes & fees
Nov 16 - Nov 17
Family Stays: Middletown, CT

20. #22- 4 Br 2 Ba house-Central CT

#22- 4 Br 2 Ba house-Central CT
New Britain
9.0 out of 10, Wonderful, (2 reviews)
"Host was great and responsive and the property was perfect for what we needed."
United States
Hilda C.
The price is ¥36,437
¥70,273 total
includes taxes & fees
Nov 7 - Nov 8
#22- 4 Br 2 Ba house-Central 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.

Learn more about South Windsor

Stroll through Nevers Road Park's lush trails or catch a show at the historic Wood Memorial Library. Hop over to nearby Hartford for world-class museums or explore the charming shops along Main Street in South Windsor's town center.

A city skyline at dusk with illuminated buildings and a prominent tower.

Top reviews in South Windsor