Wilton Vacation Packages
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Your Wilton Vacation
Reserve a Wilton vacation package and get set to experience the best of this city. Think about staying in the neighborhood of Downtown Stamford, which is great for history, bars and pubs and dining. Every trip to Wilton needs a well-thought-out itinerary. Fill yours with attractions like The Glass House, Westport Country Playhouse and Westport Farmers Market. A couple of quick clicks is all it takes to craft your perfect Wilton vacation on Expedia.
Top Wilton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,406
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
I was disappointed with our room. I specifically asked in advance for a room away from the elevator because I was traveling with my elderly mother and children. Unfortunately, we were given a room right next to the elevator, with the elevator shaft directly behind the wall. There was constant loud banging and noise, especially at night, which made it difficult to sleep. I was disappointed that my request was ignored.
Reviewed on Aug 20, 2026
1 Hotel Brooklyn Bridge
CA $2,711
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Amazing view of the city and rooftop pool is always a great time. Will be back again! Amazing staff and beautiful space.
Reviewed on Aug 17, 2026
Ready to book your vacation to Wilton?
Wilton Hotel Deals
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $240
CA $320 total
Sep 13 - Sep 14
includes taxes & fees
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
CA $259
CA $298 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,110 reviews)
"Beautiful hotel. We were just staying the night as we traveled down south but it was so nice to come into this resort and feel like a little getaway. Room was very spacious, bathroom had everything you needed. Only downside is you pay for parking and the gates were up and didn’t even need to ..."
Reviewed on Aug 20, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $206
CA $237 total
Sep 2 - Sep 3
includes taxes & fees
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 Wilton attractions
Wilton Historical Society
You can spend time studying the exhibits at Wilton Historical Society during your trip to Wilton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Gateway Shopping Center
You can search for that perfect souvenir at Gateway Shopping Center during your visit to Wilton. Savor the lively bars and top-notch restaurants while in town.
Frequently asked questions
How much does a Wilton vacation package cost?
You'll find cheap prices from CA $1,406 on Expedia for your Wilton escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Wilton costs.
What are the cheapest months to go to Wilton?
You can generally find lower prices and better availability in January, February and March. Browse our cheap Wilton vacation packages and you could get some great off-season discounts.
How many days is enough for Wilton?
For your Wilton vacation, a handful of days will be enough to explore all the highlights. Make sure to visit Westport Country Playhouse — it's one of the leading attractions in this destination. If you're after more activities, consider basing yourself here and going on some day trips from Wilton.
Is it worth booking a vacation package to Wilton?
Well known for its golfing and home to popular attractions like Wilton Historical Society, a Wilton vacation is sure to impress. Another top sight to check out? Don't miss Silvermine Golf Club.
How to find the best Wilton package deals?
Start your search for a Wilton package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Wilton package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wilton escape underway.
Is it cheaper to book a Wilton vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Wilton vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Wilton?
Score fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Wilton getaway.
How to plan a trip to Wilton?
- Pick your dates: What you'd like to do in Wilton and your favourite season will help you decide when to get away.
- Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will probably be the largest expense during your trip to Wilton.
- Decide how long to go away for: Now that you know more about Wilton, you can figure out the perfect length of your vacation. Put together a rough plan and allocate enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Wilton vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
