Stamford Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Stamford Vacation Packages

Stamford Hotel Deals

The Vine on main

The Vine on main

2 out of 5
105 Main St Stamford NY
The price is SARĀ 710 per night from Jul 20 to Jul 21
SARĀ 710
SARĀ 781 total
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (99 reviews)
"Clean room, great air conditioning, and nice wood touches"

Reviewed on 13 July 2026

The Vine on main
Ramada by Wyndham Cobleskill

Ramada by Wyndham Cobleskill

3 out of 5
121 Burgin Drive Cobleskill NY
Fully refundableReserve now, pay when you stay
The price is SARĀ 409 per night from Jul 21 to Jul 22
SARĀ 409
SARĀ 458 total
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (43 reviews)
"The room was impeccably clean with lots of towels. It was an overnight stay, so we didn't make use of any extra amenities. Breakfast in the morning was a little disappointing, with weak coffee that kept running out and almost all selections were sugary. But that wasn't a big deal. I'd happily stay ..."

Reviewed on 14 July 2026

Ramada by Wyndham Cobleskill
Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
The price is SARĀ 500 per night from Aug 9 to Aug 10
SARĀ 500
SARĀ 605 total
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (828 reviews)
"I loved the views of the mountains I hated that there is zero cellphone reception outside of the hotel there is wifi included but again once you step outside there is zero cellphone reception"

Reviewed on 16 July 2026

Hotel Vienna
See all 1,285 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.

Stay near popular Stamford attractions

Stamford Golf Club

8.0/10 (1 review)
This historic 1897 course winds through the northern Catskills with challenging holes and panoramic mountain views. Reserve your morning tee time, followed by local cuisine at Peppercorn on the Hill.
See properties

Frequently asked questions

How much does a Stamford vacation package cost?
Offering excellent value package deals 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 ā€” perfect for a budget-friendly getaway.
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 favorite 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.