Wilton Vacations from $379

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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.

The Latest Wilton vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $725, price is now $379 per person
$379
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $934, price is now $494 per person
$494
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (125 reviews)
Lovely renovation with everything new and fresh. Just a couple of things missing like a bedside clock and a hair dryer, but a quite good accommodation within easy walking distance of town.

Reviewed on Aug 19, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,262, price is now $1,236 per person
$1,236
per person
Oct 26 - Oct 29
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.

Reviewed on Aug 19, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was $934, price is now $543 per person
$543
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (495 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.

Reviewed on Aug 14, 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was $3,148, price is now $1,841 per person
$1,841
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.4/10 Exceptional! (1,262 reviews)
Clean room. Comfortable bed. Staff is great. Went to show next door. Easy comfortable trip. Cafe next door was delicious.

Reviewed on Aug 17, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Wilton

Silvermine Golf Club

Enjoy a round of golf in Wilton at Silvermine Golf Club. Savor the top-notch restaurants and lively bars while in town.

Silvermine Golf Club

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.

Gateway Shopping Center

Wilton Hotel Deals

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $143 total per night from Aug 24 to Aug 25
$143 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,294 reviews)
"Great value for the money"

Reviewed on Aug 18, 2025

Norwalk Inn & Conference Center
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $116 total per night from Aug 20 to Aug 21
$116 total
Aug 20 - Aug 21
Total includes taxes and fees
8.4/10 Very Good! (1,642 reviews)
Good stay but could use a renovation!
"My partner and I stayed for one night here, we had a pleasant enough stay. Quick check in, plenty of parking. However the hotel clearly needs to be updated, it feels like the hotel is right out of the 90s. The bed was decently comfortable but I was glad we brought our own pillows. Definitely a good ..."

Reviewed on Aug 15, 2025

Amsterdam Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave, White Plains, NY
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $231 total per night from Sep 1 to Sep 2
$231 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,104 reviews)
"Excellent welcoming front desk staff!"

Reviewed on Aug 18, 2025

Sonesta White Plains Downtown
See all 1,151 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.

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Frequently asked questions

How much does a Wilton vacation package cost?
You can grab a vacation package to this destination from $379 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.