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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 7 hours ago
Roundtrip flight included
Toronto (YTO) 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

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,783, price is now CA $3,371 per person
CA $3,371
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was CA $1,953, price is now CA $1,164 per person
CA $1,164
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,271 reviews)
Wonderful property, accesible to multiple subway stations. Walkable distance to plenty of sites and attractions. Great costumer service!

Reviewed on Aug. 20, 2025

W New York - Times Square

W New York - Times Square

4.5 out of 5
Manhattan
Price was CA $1,343, price is now CA $818 per person
CA $818
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,740 reviews)
Amazing location, just off Times Square! Excellent air con, large clean rooms and comfortable beds. Nice toiletries too

Reviewed on Aug. 19, 2025

Ready to book your vacation to Wilton?

 

Choose your dates

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
The price is CA $173 per night from Aug 24 to Aug 25
CA $173
CA $200 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,291 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
The price is CA $115 per night from Sep 8 to Sep 9
CA $115
CA $134 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very Good! (1,637 reviews)
"Good deal for the price. Room clean, staff always pleasant, professional and helpful"

Reviewed on Aug. 19, 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 $245 per night from Sep 21 to Sep 22
CA $245
CA $320 total
Sep 21 - Sep 22
includes taxes & 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.
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 $560 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.