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.
Echo Valley Cottages

Echo Valley Cottages

3 out of 5
Price was CA $1,761, price is now CA $1,064 per person
CA $1,064
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.6/10 Excellent! (62 reviews)
The place was very clean and the manager was excellent. Definitely would go back.

Reviewed on Jun 25, 2026

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $2,850, price is now CA $1,425 per person
CA $1,425
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
A 10 all around.

Reviewed on Jul 5, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,519, price is now CA $2,841 per person
CA $2,841
per person
Aug 21 - Aug 25
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,972, price is now CA $9,484 per person
CA $9,484
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,176 per person
CA $1,176
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
💯

Reviewed on Jul 5, 2026

Ready to book your vacation to Wilton?

 

Choose your dates

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
The price is CA $337 per night from Jul 20 to Jul 21
CA $337
CA $387 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,061 reviews)
"There wasn't a porter anywhere to help us with iur luuggage. The hallway carpets needed a cleaning and typically most hotels have coffee available in the morning free of charge."

Reviewed on Jul 5, 2026

Hyatt Regency Greenwich
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 $264 per night from Jul 26 to Jul 27
CA $264
CA $349 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,320 reviews)
"Nicely renovated property."

Reviewed on Jul 4, 2026

Sonesta White Plains Downtown
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Aug 4 to Aug 5
CA $142
CA $163 total
Aug 4 - Aug 5
includes taxes & fees
6.6/10 (1,512 reviews)
"Staff was great. Convenient location as well"

Reviewed on Jul 5, 2026

La Quinta Inn & Suites by Wyndham Stamford / New York City
See all 1,179 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
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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.
See properties

Frequently asked questions

How much does a Wilton vacation package cost?
You'll find cheap prices from CA $1,064 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.