Stamford Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    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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    Rest easy

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

Your Stamford Vacation

Experience the energy and excitement of Stamford with a customized Stamford vacation package. From its rich history to its cultural experiences, you'll never have a dull moment in this city. Can't wait to sightsee? Spend your days enjoying well-known attractions like Stamford Golf Club during your trip to Stamford. No matter your travel plans or the size of your budget, organizing a tailored Stamford vacation is a breeze with Expedia.

Top Stamford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

2 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
7.6/10 Good! (1,001 reviews)
Older but very clean. Pool was nice. Everyone was very nice and helpful. Restaurant had very good food and reasonably priced

Reviewed on Jul. 7, 2025

Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast

4 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
10/10 Exceptional! (4 reviews)
This property is gorgeous and the owners did an amazing job at creating a tranquil environment for their guests to enjoy. The check-in process is seamless, the food is delicious, and the rooms are clean and comfortable. We would highly recommend and absolutely come back ourselves.

Reviewed on Apr. 23, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
9/10 Wonderful! (399 reviews)
The experience is different and cool but the pricing is super aggressive for what you get. It’s very nice camping sold as a five star hotel.

Reviewed on Jul. 6, 2025

Inn at Pine Plains

Inn at Pine Plains

3.5 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
9.8/10 Exceptional! (286 reviews)
It's a beautiful property! The staff did an excellent job making our stay perfect. Our rooms were lovely. Breakfast was delicious. Thanks for making our stay a wonderful experience.

Reviewed on Jun. 20, 2025

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

2.5 out of 5
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hudson (HCC)
8.8/10 Excellent! (625 reviews)
The hotel is in a very convenient location. The hotel was very clean, the front desk staff was extremely friendly, and the towels and bedding were perfectly clean every day. It was a very nice stay and hotel overall.

Reviewed on Jul. 6, 2025

Ready to book your vacation to Stamford?

 

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Stamford Hotel Deals

The Vine on main
The Vine on main
2 out of 5
105 Main St, Stamford, NY
The price is CA $246 per night from Jul 11 to Jul 12
CA $246
CA $271 total
Jul 11 - Jul 12
includes taxes & fees
7.8/10 Good! (77 reviews)
"A positive experience overall. The door knob to the bathroom fell off when we first used it and the mini fridge did not work, but we kept our cooler stuff refrigerated in the lobby fridge"

Reviewed on Jun. 25, 2025

The Vine on main
Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 13 to Jul 14
CA $178
CA $193 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (584 reviews)
"People were great. It was modern and extremely clean. The bed was very comfortable. Great shower."

Reviewed on Jul. 6, 2025

Hotel Vienna
Quality Inn Oneonta Cooperstown Area
Quality Inn Oneonta Cooperstown Area
2.5 out of 5
5206 State Highway 23, Oneonta, NY
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Jul 20 to Jul 21
CA $285
CA $325 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Basic hotel but very clean and good customer service."

Reviewed on Jul. 5, 2025

Quality Inn Oneonta Cooperstown Area
See all 1,229 properties in Stamford
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

Discover the most popular places to visit in Stamford

Stamford Golf Club

Enjoy a round of golf in Stamford at Stamford Golf Club. Wander the forest and lakeside while you're in the area.

Stamford Golf Club

Frequently asked questions

How much does a Stamford vacation package cost?
Offering excellent value package deals from CA $549 on Expedia, you'll be pleasantly surprised at how much a vacation to Stamford costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Stamford?
If you'd like to score a cheap Stamford vacation package, consider planning a trip in January, April and December. You'll generally find better prices on accommodations and flights during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Stamford?
With a well-organized itinerary, you can easily tick off the main Stamford attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Stamford vacation for longer.
How to find the best Stamford package deals?
Begin your search for a Stamford package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Stamford package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Stamford adventure underway.
Is it cheaper to book a Stamford vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Stamford vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Stamford?
Secure amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Stamford trip.
How to plan a trip to Stamford?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Stamford.
  2. Plan your budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may come up during your trip to Stamford.
  3. Decide how long to go for: Now that you know more about Stamford, you can figure out the right length of your vacation. Pull together a draft itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Stamford vacation package.

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