A rustic barn surrounded by autumn foliage and a field.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Windsor holiday homes

Dining

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
Windsor
9.4 out of 10, Exceptional, (12 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 HK$2,571
HK$5,646 total
includes taxes & fees
15 Sept - 16 Sept
Spacious Yard w/ Gazebo: Charming Windsor Retreat
Living area

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is HK$699
HK$960 total
includes taxes & fees
8 Sept - 9 Sept
Entire guest suite in South Windsor, Connecticut
Living area

3. The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (16 reviews)
"The property was clean and inviting. The basement game room was amazing"
United States
Michael P.
The price is HK$1,058
HK$2,782 total
includes taxes & fees
14 Sept - 15 Sept
The Serene Skyway Retreat
Interior

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 HK$1,058
HK$2,354 total
includes taxes & fees
14 Sept - 15 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Living area

5. 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 HK$974
HK$3,413 total
includes taxes & fees
14 Sept - 15 Sept
Willow Haven 2BR Cozy Retreat, Close to Hartford
Living area

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, (29 reviews)
"Was a great stay"
United States
John S.
The price is HK$1,168
HK$2,511 total
includes taxes & fees
20 Sept - 21 Sept
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Private kitchen

7. 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, (11 reviews)
"Great stay, home was comfortable and communication w owner was very smooth!"
United States
Stacey P.
The price is HK$1,976
HK$4,169 total
includes taxes & fees
9 Sept - 10 Sept
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Dining

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

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is HK$1,333
HK$2,709 total
includes taxes & fees
10 Sept - 11 Sept
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Exterior

9. Red Door Retreat

Red Door Retreat
Vernon
The price is HK$1,435
HK$2,407 total
includes taxes & fees
6 Oct - 7 Oct
Red Door Retreat
Dining

10. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 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 HK$2,108
HK$4,095 total
includes taxes & fees
14 Sept - 15 Sept
Prime West Hartford Center: Timeless Charm
Property grounds

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 HK$690
HK$2,256 total
includes taxes & fees
9 Sept - 10 Sept
Sun Filled Lake House Living
Interior

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

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is HK$1,470
HK$2,962 total
includes taxes & fees
13 Sept - 14 Sept
Linny's - Private Dock - Lake Access - Firepit
Outdoor dining

13. Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem
West Hartford
10.0 out of 10, Exceptional, (35 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 HK$2,701
HK$4,896 total
includes taxes & fees
15 Sept - 16 Sept
Prime West Hartford Center Location: Historic Gem
Terrace/patio

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 HK$1,482
HK$3,672 total
includes taxes & fees
10 Sept - 11 Sept
The Old Avon 1800 Manor
Room

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
9.6 out of 10, Exceptional, (8 reviews)
"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...
United States
Jenny
The price is HK$1,284
HK$2,933 total
includes taxes & fees
15 Sept - 16 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Private kitchen

16. Spacious & Newly Renovated Longmeadow Getaway

Spacious & Newly Renovated Longmeadow Getaway
Longmeadow
6.0 out of 10, (2 reviews)
"Great location. Comfortable beds. Good air conditioning."
United States
Matt K.
The price is HK$2,235
HK$4,029 total
includes taxes & fees
5 Oct - 6 Oct
Spacious & Newly Renovated Longmeadow Getaway
Property grounds

17. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is HK$1,669
HK$3,237 total
includes taxes & fees
28 Sept - 29 Sept
#24 Serenity A Lakefront Cottage Retreat
Outdoor dining

18. 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, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,446
HK$4,145 total
includes taxes & fees
10 Sept - 11 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Living area

19. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (46 reviews)
"It was nice stay!"
United States
Lorrie
The price is HK$1,411
HK$2,837 total
includes taxes & fees
7 Sept - 8 Sept
Cozy & Spacious Entire Home in 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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

8/10 Good
"Great overnight stay. Our room was clean and stocked with items."
Keion 1-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
281
Accommodation
220 Vacation Homes
Lowest Price
HK$960
Highest Price
HK$5,646

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