Wilton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,431 reviews)
This is my 3rd stay at this hotel and as always i enjoyed myself. The amenities, the staff, the surrounding areas, and the spectacular views, make for an amazing stay.

Reviewed on Jun. 2, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on Jun. 25, 2025

Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very Good! (120 reviews)
I only stayed one night because I had an evening event in the area. I wish I would have stayed longer. It would have been a great place for me to get some rest and it inspired me as an author to write. I was also able to walk to the beach. I could have ridden one of the provided bikes. Lovely serene place. Also close to many eclectic shops and restaurants

Reviewed on Jul. 5, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (531 reviews)
We had an overall great stay and will be back. Especially loved nights out on the beach!

Reviewed on Jun. 22, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
7.6/10 Good! (803 reviews)
Best experience ever!! Fabulous staff and cleanliness

Reviewed on Jul. 5, 2025

Ready to book your vacation to Wilton?

 

Choose your dates

Wilton Hotel Deals

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $152 per night from Jul 27 to Jul 28
CA $152
CA $175 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great place"

Reviewed on Jun. 30, 2025

EVEN Hotel Norwalk by IHG
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jul 10 to Jul 11
CA $117
CA $136 total
Jul 10 - Jul 11
includes taxes & fees
8.4/10 Very Good! (1,596 reviews)
"A lot of people were smoking"

Reviewed on Jul. 2, 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
The price is CA $236 per night from Aug 3 to Aug 4
CA $236
CA $309 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,084 reviews)
"Very nice"

Reviewed on Jun. 30, 2025

Sonesta White Plains Downtown
See all 1,145 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Wilton vacation package cost?
You'll find cheap prices from CA $729 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?

  1. Pick your dates: What you'd like to do in Wilton and your favourite season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.