Top hotels in Windsor
Marriott Hartford/Windsor Airport
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
S$211
28 Aug - 29 Aug
includes taxes & fees
Courtyard By Marriott Hartford/Windsor Airport
1 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
S$211
6 Sept - 7 Sept
includes taxes & fees
Residence Inn by Marriott Hartford/Windsor
100 Dunfey Ln Windsor CT
Fully refundableReserve now, pay when you stay
S$181
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (782 reviews)
"great staff, everyones cheery and helpful, felt like home"
Reviewed on 13 Aug, 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.
Stay near popular Windsor attractions
Northwest Park
7.8/10 (24 reviews)
Explore 473 acres of diverse habitats through 12 miles of scenic trails at this natural retreat. The nature center's educational exhibits and heritage breed farm create an immersive outdoor experience for all ages.
Loomis Chaffee School
This prestigious New England boarding school blends historic architecture with state-of-the-art facilities. Schedule a guided campus tour to experience Loomis Chaffee's innovative learning spaces and picturesque grounds.
Windsor Arts Center
7.6/10 (18 reviews)
This historic freight house turned art centre showcases contemporary New England art in a charming railway setting. Enjoy rotating exhibitions while soaking in the creative atmosphere of Windsor's cultural hub.
Oliver Ellsworth Homestead
8.2/10 (15 reviews)
Step back in time at Elmwood, home of Oliver Ellsworth who helped draft the US Constitution. Explore period furnishings and family artefacts in this beautifully preserved 18th-century residence.
Vintage Radio and Communications Museum of Connecticut
7.6/10 (13 reviews)
This time-traveling museum showcases communication technology from the 1800s to modern computers. Tap out Morse code messages and tune vintage radios while knowledgeable volunteers bring history to life.
Windsor Historical Society
8.0/10 (12 reviews)
Step into Connecticut's oldest English settlement at the Windsor Historical Society's museum complex. Explore two historic homes dating to the 1700s and try on colonial costumes in the hands-on learning centre.
Windsor Meadows State Park
7.6/10 (10 reviews)
This riverside haven offers peaceful trails winding through floodplain forests with Connecticut River views. Explore the meadows or launch your boat for a day of fishing and serene water adventures.
What to do in Windsor
Connecticut Coloured Regiment Parade Route: An Audio Tour
S$13
per adult
Massachusetts: Six Flags New England Admission Ticket
S$58
per adult
Frequently asked questions
How much does a Windsor holiday package cost?
You'll find cheap prices 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 holiday to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and greater availability in December, January and February. Explore our cheap Windsor holiday packages and you could score some great off-season discounts.
How many days is enough for Windsor?
With about 2 days, you'll have enough time to visit popular neighbourhoods like Downtown Hartford and North Meadows during your Windsor holiday. Be sure to also add Oliver Ellsworth Homestead and SS&C SummerWind Performing Arts Centre to your list of must-sees. In the mood for more adventures? Consider exploring outside of Windsor on tours and day trips.
Is it worth booking a holiday package to Windsor?
Whether you want to check out top sights such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor holiday, or coming for its great history, festivals and culture, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many visitors think Windsor is a good holiday 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 customise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Windsor?
If you're planning a spur-of-the-moment Windsor holiday, 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?
- Pick your travel dates: What you want to do in Windsor and your preferred season will help you decide when to go.
- Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Windsor.
- Decide your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Windsor holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
