How much does a Windsor vacation package cost?

You'll find cheap prices from $469 on Expedia for your Windsor break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Windsor costs.

What are the cheapest months to go to Windsor?

If you're looking to score a cheap Windsor vacation package, consider visiting in December, January and February. You're likely to find better prices on hotels and airfares during these quieter months — ideal for a budget-friendly break.

How many days is enough for Windsor?

We recommend planning a Windsor vacation for around 2 days. This will allow you time to visit popular sights such as Northwest Park and Oliver Ellsworth Homestead , and check out neighborhoods like Downtown Hartford and North Meadows. You might even be able to fit in a day trip or two beyond Windsor.

Is it worth booking a vacation package to Windsor?

Whether you're looking to explore attractions such as Windsor Arts Center and Windsor Historical Society on your Windsor vacation, or coming for its excellent history, festivals and culture, there's something for everyone here. With so many things to do, you'll soon learn why so many travelers think Windsor is a good vacation destination.

How to find the best Windsor package deals?

Bagging a cheap Windsor package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.

Is it cheaper to book a Windsor vacation as a package?

You can enjoy significant savings on your next Windsor getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.

When to book a vacation package to Windsor?

If you're planning a spur-of-the-moment Windsor vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.

How to plan a trip to Windsor?

Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Windsor. Plan your budget wisely: As well as the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Windsor. Organize your Windsor escape with Expedia's trip planning tool : Look for and book accommodations and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Windsor together. Work out your trip length: Consider how long you'd like to spend discovering Windsor. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Windsor vacation package. Add on experiences and excursions: Read our travel guide to find some fun things to do in Windsor . Book tickets or make reservations in advance to save time and avoid the stress of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Windsor vacation packages?

Your Windsor getaway is meant to be an escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Windsor Vacation Packages 2026 from $469

Your Windsor Vacation

The cosmopolitan vibe and rich history are just the beginning of the things Windsor has going for it. Enjoy the best parts of this fascinating city your way with a personalized Windsor vacation package. A trip to Windsor is an ideal opportunity to see the sights. Be sure to stop by big-name attractions such as XL Center, Xfinity Theatre and University of Hartford. Whatever your travel plans or budget, putting together the ultimate tailored Windsor vacation is simple with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Place Milford / New Haven

$469

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

8.6/10 Excellent! (1,184 reviews)

Room was spotless the staff was amazing. Room fully stocked with amenities. Had a great stay! The only down side was there were no microwaves in the rooms.

Reviewed on Feb 3, 2026

Graduate by Hilton New Haven

Downtown New Haven

$579

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

9.2/10 Wonderful! (908 reviews)

Great location to explore Yale. Quiet, comfortable & smartly appointed.

Reviewed on Jan 25, 2026

Cambria Hotel New Haven University Area

West River

$471

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

8.8/10 Excellent! (966 reviews)

Room matched pictures. Front desk people were excey

Reviewed on Jan 21, 2026

Luxury Apartments by Hyatus at Pierpont

The Hill

$679

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

9.4/10 Exceptional! (21 reviews)

Very quiet, clean and peaceful accommodation. Enjoyed our stay here. Very spacious apartment with everything you need for a comfortable stay. Felt right at home - away from home. Highly recommend.

Reviewed on Jan 7, 2026

Cheshire Welcome Inn

$482

per person

Mar 15 - Mar 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

8.4/10 Very Good! (755 reviews)

Great location, comfortable and clean

Reviewed on Feb 5, 2026

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Windsor Hotel Deals

Residence Inn by Marriott Hartford/Windsor

100 Dunfey Ln Windsor CT

Fully refundableReserve now, pay when you stay

$113 nightly

$130 total

Feb 22 - Feb 23

Total with taxes and fees

8.2/10 Very Good! (697 reviews)

Exceeded all expectations! The staff were incredibly welcoming, the service was seamless, and my room was spotless and comfortable. 10/10 would stay again!

Reviewed on Jan 25, 2026

Hampton Inn Hartford/Airport

2168 Poquonock Ave Windsor CT

Fully refundableReserve now, pay when you stay

$113 nightly

$130 total

Feb 15 - Feb 16

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

Clean. Friendly. Convenient to highway.

Reviewed on Jan 27, 2026

HYATT house Hartford North/Windsor

200 Corporate Dr Windsor CT

Fully refundableReserve now, pay when you stay

$136 nightly

$156 total

Feb 13 - Feb 14

Total with taxes and fees

9/10 Wonderful! (1,002 reviews)

The best place like a 5 star hotel

Reviewed on Feb 4, 2026

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.

Things to do in and around Windsor

Windsor, Connecticut, offers a delightful mix of family-friendly activities, outdoor adventures, and romantic getaways. Visitors can enjoy educational attractions, music concerts, and relaxing stays at local resorts. Exciting options include exploring popular attractions and an adventure park, making it an ideal destination for memorable trips to Windsor. Whether you're seeking fun or relaxation, Windsor has something for everyone.

Shopping

In Windsor, you can shop at Bloomfield Crossing, just 5 miles away, offering a variety of stores with a family-friendly vibe. The Shoppes at Buckland Hills, located 6 miles away, features entertainment and shopping in a lively atmosphere. If you're up for a drive, check out Hartford Downtown Farmers Market, 6 miles away.

Recreation

Xfinity Theatre, located 5 miles from Windsor, offers a vibrant atmosphere filled with culture and romance, perfect for an entertaining evening. The XL Center, 6 miles away, brings sports excitement, while the SS&C SummerWind Performing Arts Center in Windsor provides delightful musical performances for a relaxing night out.

Adventure

Experience thrills at Nomads Adventure Quest, an arcade adventure zone only 2 miles from Windsor, or strike down pins at Callahan's Bowl a Rama, located 11 miles away. For a unique challenge, head to Assaiante Tennis Center, 8 miles away, perfect for tennis enthusiasts seeking adventure.

Nightlife

Windsor offers a charming nightlife with cozy pubs like the Windsor Pub for casual drinks, while the nearby Blue Back Square in West Hartford features lively bars and restaurants for a vibrant evening. Enjoy live music at local venues or unwind at a laid-back café for a relaxed night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windsor

Windsor, Connecticut, is a charming destination perfect for family outings, outdoor adventures, and romantic getaways. Visitors can enjoy a variety of attractions, including urban parks, historic houses, and renowned colleges. The town offers a blend of cultural experiences and outdoor activities, making it an ideal spot for travelers seeking both relaxation and exploration. Whether you're interested in history or nature, Windsor has something to offer for everyone.

Connecticut Convention Center: Located only 6 miles from Windsor, this modern event venue buzzes with business vibes. It hosts a variety of conferences and exhibitions, making it a hub for networking and innovation. Enjoy its spacious layout and impressive architecture while attending events or exploring nearby dining options.
Six Flags New England: A thrilling 13 miles from Windsor, this amusement park is perfect for families and adventure seekers. With exhilarating rides, entertaining shows, and family-friendly attractions, it promises a fun-filled day outdoors, creating unforgettable memories for visitors of all ages.
Mark Twain House & Museum: Just 7 miles away, this historic house offers a glimpse into the life of the famed author. Explore the beautifully preserved home, and immerse yourself in rich cultural history through exhibits showcasing Twain's literary legacy and impact on American literature.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	27.9°F (-2.3°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.3°F (-1.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Sunny	Average	Average
April	48.4°F (9.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Average
September	65.1°F (18.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Windsor

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Windsor.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language	English
Currency	U.S dollars
Closest Airport	Bradley Intl. Airport (BDL)
Population	28,800
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	Xfinity Theatre, Connecticut Science Center and Talcott Mountain State Park

Language

English

Currency

U.S dollars

Closest Airport

Bradley Intl. Airport (BDL)

Population

28,800

Max Temp Winter

35ºF

Max Temp Summer

80ºF