Wilton Vacations from $455

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Wilton vacation packages

Price found within the past 48 hours. Click for updated prices.
Dolce by Wyndham Parsippany

Dolce by Wyndham Parsippany

4 out of 5
Save 100% on your flight
Price was $756, price is now $455 per person
$455
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.2/10 Very Good! (1,016 reviews)
Excellent experience, place was conveniently located, super clean, and great hospitality.

Reviewed on Oct 27, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $3,955, price is now $1,938 per person
$1,938
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
No reviews

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $3,494, price is now $1,999 per person
$1,999
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was $961, price is now $552 per person
$552
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (3,805 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,240, price is now $754 per person
$754
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Wilton
View all trips

Stay near popular Wilton attractions

Wilton Historical Society

Step back in time at this living museum where 18th-century homes and a working blacksmith shop tell Wilton's story. Join hands-on workshops in weaving or hearth cooking for an immersive taste of New England's past.
See properties

Wilton Hotel Deals

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $225 total per night from Nov 19 to Nov 20
$225 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,193 reviews)
"I will definitely be back. such a great hotel. Especially love the lobby and staff; the rooms are super cute and cozy."

Reviewed on Oct 27, 2026

Hyatt Regency Greenwich
J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
$312 nightly
The price is $358 total per night from Nov 20 to Nov 21
$358 total
Nov 20 - Nov 21
Total with taxes and fees
J House Greenwich
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
2701 Summer St Stamford CT
$189 nightly
The price is $217 total per night from Oct 29 to Oct 30
$217 total
Oct 29 - Oct 30
Total with taxes and fees
The Armon Stamford Hotel & Conference
See all 1,195 properties in Wilton
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.

Find the Best Wilton Vacation Packages

Wilton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
18,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Wilton vacation package cost?
You can grab a vacation package to this destination from $455 on Expedia. But how much your vacation to Wilton costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Wilton?
If you're hoping to score a cheap Wilton vacation package, consider traveling in December, January and February. You'll usually find better prices on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Wilton?
You can visit all the major sights in Wilton in a few days, including the popular Gateway Shopping Center. If you want an extended Wilton vacation, look at which kind of activities and excursions are available nearby.
Is it worth booking a vacation package to Wilton?
Boasting a host of highlights starting with its excellent golfing, Wilton is a good vacation destination. Whether you'd like to visit sights such as Wilton Historical Society and Silvermine Golf Club or venture off the beaten track, you'll find plenty to see and do on your Wilton vacation.
How to find the best Wilton package deals?
Begin your search for a Wilton package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Wilton package deal right away, just tweak your dates and search again. Bear in mind 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?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can tailor your Wilton escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Wilton?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Wilton vacation.
Does Expedia offer Book Now, Pay Later Wilton vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Wilton vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.