Windsor Vacations from $383
Book a Hotel + Flight or Car together to unlock savings
The Latest Windsor Vacation Packages
- Aderi Hotel Niantic
Sep 21 - Sep 26Aderi Hotel Niantic + Flight
Niantic5 nights2.0 star property6.2/10 - (715 reviews)"The A/c didnt work well , and neither did the room fridge."Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - Hartford (BDL)ATL - JFK • Nonstop JFK - ATL • Nonstop$487$383found 1 day agoper traveler - Luxury Furnished Apartments by Hyatus Downtown at Yale
Aug 21 - Aug 24Luxury Furnished Apartments by Hyatus Downtown at Yale + Flight
The Hill3 nights3.5 star property9.6/10 - Exceptional (85 reviews)"I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!"Reviewed July 6, 2026Roundtrip • Tampa (TPA) - New Haven (HVN)TPA - BDL • Nonstop BDL - TPA • Nonstop - Pier Blue Inn Old Saybrook - Essex
Sep 21 - Sep 26Pier Blue Inn Old Saybrook - Essex + Flight
Saybrook Manor5 nights2.0 star property8.0/10 - Very Good (1,006 reviews)"Lived my room- one queen bed, big bathroom, beautiful dinette very clean. I would recommend that room if I was going there again."Reviewed July 19, 2026Roundtrip • Atlanta (ATL) - New Haven (HVN)ATL - JFK • Nonstop JFK - ATL • Nonstop - Landing Apartments New Haven Near Dixwell
Aug 26 - Aug 31Landing Apartments New Haven Near Dixwell + Flight
Newhallville5 nights3.0 star property2.0/10 - (1 review)"The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host."Reviewed May 25, 2026Roundtrip • Atlanta (ATL) - New Haven (HVN)ATL - HVN • Nonstop HVN - ATL • Nonstop - Delamar West Hartford
Aug 26 - Aug 31Delamar West Hartford + Flight
West Hartford5 nights4.0 star property9.8/10 - Exceptional (1,003 reviews)"I had issues with food and room charges when I went to the front desk they said they were not part of the restaurant so I would have to discuss the issue with them. Which I did the restaurant staff were excellent and did resolve the issue. However when I checked out the front desk said there were not additional charges and they would email the receipt. I never received the receipt I attempted on numerous times to contact the hotel since they did however charge my credit card $300 plus!! The..."Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Hartford (BDL)ATL - BDL • Nonstop BDL - ATL • Nonstop
Discover the most popular places to visit in Windsor
What to do in Windsor
Connecticut Coloured Regiment Parade Route: An Audio Tour
Windsor Hotel Deals
Marriott Hartford/Windsor Airport
Marriott Hartford/Windsor Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport
HYATT house Hartford North/Windsor
HYATT house Hartford North/Windsor
Courtyard By Marriott Hartford/Windsor Airport
Courtyard By Marriott Hartford/Windsor Airport
Residence Inn by Marriott Hartford/Windsor
Residence Inn by Marriott Hartford/Windsor
Baymont by Wyndham East Windsor Bradley Airport
Baymont by Wyndham East Windsor Bradley Airport
Holiday Inn Express & Suites Bradley Airport by IHG
Holiday Inn Express & Suites Bradley Airport by IHGFrequently Asked Questions
How much does a Windsor vacation package cost?
You'll find cheap prices from $383 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.
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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.
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.
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.