A rustic barn surrounded by autumn foliage and a field.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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)
"Good location"
United States
Arthur
Entire guest suite in South Windsor, Connecticut
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.

2. 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 AED 1,627
AED 2,830 total
includes taxes & fees
25 Nov - 26 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.

3. 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 AED 514
AED 1,135 total
includes taxes & fees
1 Nov - 2 Nov
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.

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 AED 511
AED 1,131 total
includes taxes & fees
1 Nov - 2 Nov
Modern & Cozy Cape | 4 Bedroom House | Central Location
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

5. 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 AED 833
AED 1,725 total
includes taxes & fees
26 Oct - 27 Oct
Charming New England Home in West Hartford Center
Dining

6. 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.
Prime West Hartford Center | Timeless Charm
A hallway with a wooden door, a gray couch, a dining table with chairs, and a trash can.

7. Red Door Retreat

Red Door Retreat
Vernon
Red Door Retreat
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

8. 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 AED 250
AED 964 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A patio area with wicker furniture and a brick floor.

9. 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 AED 654
AED 1,664 total
includes taxes & fees
4 Nov - 5 Nov
The Old Avon 1800 Manor
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

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, (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 AED 569
AED 1,325 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Property grounds

11. 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 AED 918
AED 1,655 total
includes taxes & fees
3 Nov - 4 Nov
Lakefront Property with Scenic View - All Seasons!
A bedroom with a bed, dresser, and floor lamp.

12. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AED 658
AED 913 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-Bedroom Springfield Home 1.5 Baths
A stone fire pit with two Adirondack chairs and a wooden bench, surrounded by a white fence and trees.

13. 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 AED 612
AED 777 total
includes taxes & fees
4 Nov - 5 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
A modern living room with a sofa, a coffee table, and a red patterned rug.

14. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (52 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 AED 612
AED 1,265 total
includes taxes & fees
26 Oct - 27 Oct
Cozy & Spacious Entire Home in Springfield
A patio with a table and chairs, a grill, and a view of a lake.

15. 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 AED 1,146
AED 1,931 total
includes taxes & fees
29 Oct - 30 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a porch, a large tree in front, and a mailbox.

16. 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.
Saint James Manor - Sleeps 24 in Style & Comfort with Parking
Veterans Park, near the house

17. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is AED 470
AED 910 total
includes taxes & fees
3 Nov - 4 Nov
Family Stays: Middletown, CT
A covered porch with two black wicker chairs and a small table, a striped rug, and a view of neighboring houses and a fire truck.

18. Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
9.8 out of 10, Exceptional, (16 reviews)
"The hosts were super accommodating. The house was very clean with towels and shower stuff available."
United States
Julia S.
The price is AED 1,396
AED 2,742 total
includes taxes & fees
22 Nov - 23 Nov
Beautiful 4BR 2 Bathroom House with Parking
A living room with a green sofa, a fireplace, and a television.

19. Stylish 4BR 2 Bathroom Home in Forest Park

Stylish 4BR 2 Bathroom Home in Forest Park
Forest Park
10.0 out of 10, Exceptional, (5 reviews)
"The house was in a great location it was minutes away from the Big E Fairgrounds and MGM Casino."
United States
HEATHER D.
The price is AED 1,469
AED 2,838 total
includes taxes & fees
22 Nov - 23 Nov
Stylish 4BR 2 Bathroom Home in Forest Park
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

20. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.8 out of 10, Excellent, (23 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is AED 661
AED 1,446 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"Good breakfast Clean room Perfect for a stay"
Guillaume 1-night trip
Posted 15 hours ago
Holiday Inn Express Southington by IHG