Holiday Packages in Windsor, Connecticut

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Tips for booking hotels in Windsor

Gain useful insights to help choose a hotel in Windsor. Data was last updated on Fri Aug 14 2026.

Cheapest month:February
Most expensive month:June
Average price in Windsor:£126/night
Cheapest price found:£100/night
Cheapest day:Sunday
Most expensive day:Monday
£100 - £180
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£109 - £137
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Windsor vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Fri Aug 14 2026.
Marriott Hartford/Windsor Airport
Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

28 Day Hill Road, Windsor, CT, United States
0.0 mi from city centre
Pool
Parking
£1,078
Avg. per night
View Deal
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

555 Corporate Drive, Windsor, CT, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,104
Avg. per night
View Deal
Hampton Inn Hartford-Airport
Hampton Inn Hartford-Airport

Hampton Inn Hartford-Airport

2168 Poquonock Avenue, Windsor, CT, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£1,104
Avg. per night
View Deal
Homewood Suites by Hilton Windsor Locks Hartford
Homewood Suites by Hilton Windsor Locks Hartford

Homewood Suites by Hilton Windsor Locks Hartford

65 Ella Grasso Turnpike, Windsor Locks, CT, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,156
Avg. per night
View Deal
Residence Inn by Marriott Hartford Windsor
Residence Inn by Marriott Hartford Windsor

Residence Inn by Marriott Hartford Windsor

100 Dunfey Lane, Windsor, CT, United States
0.0 mi from city centre
Free Wi-Fi
£1,254
Avg. per night
View Deal
Sheraton Hartford Hotel at Bradley Airport
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

1 Bradley International Airport, Windsor Locks, CT, United States
0.0 mi from city centre
Free Wi-Fi
£1,242
Avg. per night
View Deal
DoubleTree by Hilton Hartford - Bradley Airport
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

16 Ella T. Grasso Turnpike, Windsor Locks, CT, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£1,130
Avg. per night
View Deal
Hyatt House Hartford North Windsor
Hyatt House Hartford North Windsor

Hyatt House Hartford North Windsor

200 Corporate Drive, Windsor, CT, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£1,047
Avg. per night
View Deal
SpringHill Suites by Marriott Hartford Airport/Windsor Locks
SpringHill Suites by Marriott Hartford Airport/Windsor Locks

SpringHill Suites by Marriott Hartford Airport/Windsor Locks

225 Ella Grasso Tpke, Windsor Locks, CT, United States
0.0 mi from city centre
Pool
£1,197
Avg. per night
View Deal
Courtyard by Marriott Hartford/Windsor Airport
Courtyard by Marriott Hartford/Windsor Airport

Courtyard by Marriott Hartford/Windsor Airport

1 Day Hill Road, Windsor, CT, United States
0.0 mi from city centre
Free Wi-Fi
£990
Avg. per night
View Deal
See all

Where to stay in Windsor

Utilise the map to find the perfect place to stay for your trip to Windsor. There are 11 hotels to choose from in Windsor.

FAQ about Windsor holiday packages

Find answers to frequently asked questions Cheapflights users have about Windsor holiday deals.

  • How much are vacation packages to Windsor?

    The cheapest price of a Windsor flight+hotel is currently £990.

  • What is the cheapest time of year to travel to Windsor?

    If you're looking for the cheapest month of the year to book a holiday package to Windsor, March is ideal.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Yes! Holidays on Cheapflights are designed to help users save money by bundling their flight, car rental, and hotel.

  • What other destinations does Windsor have flight+hotel deals to?

    In addition to Windsor, Cheapflights also offers holiday packages to Connecticut

See more FAQs

Other popular holiday deals in Connecticut

Consider booking a Flight+Hotel in one of these other areas of Connecticut.
Connecticut holidays
New London holidays
Norwalk holidays
Hartford holidays
Waterbury holidays