Stamford Vacations from $661

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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.

The Latest Stamford vacation packages

Price found within the past 48 hours. Click for updated prices.
Little Cat Lodge

Little Cat Lodge

2 out of 5
Price was $749, price is now $661 per person
$661
per person
Apr 10 - Apr 13
found 22 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Hudson (HCC)
9.4/10 Exceptional! (64 reviews)
Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed.

Reviewed on Dec 2, 2025

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Save 100% on your flight
Price was $2,742, price is now $2,298 per person
$2,298
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Deer Mountain Inn

Deer Mountain Inn

2 out of 5
Price was $1,469, price is now $1,246 per person
$1,246
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (4 reviews)
I loved the guest room with the pool table and self attend bar.

Reviewed on Oct 22, 2024

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,084, price is now $941 per person
$941
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
8.6/10 Excellent! (17 reviews)
I loved the view and the area

Reviewed on Jul 31, 2025

Eastwind Windham

Eastwind Windham

2 out of 5
Price was $981, price is now $865 per person
$865
per person
Mar 25 - Mar 29
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9.2/10 Wonderful! (67 reviews)
This is one of the most amazing weekend vacations I have been on. I can’t complain about anything!

Reviewed on Jan 5, 2026

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Stamford Hotel Deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $172 total per night from Jan 20 to Jan 21
$172 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
Nice rooms and continental breakfast. Very reasonable price.

Reviewed on Jan 13, 2026

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
$71 nightly
The price is $81 total per night from Jan 21 to Jan 22
$81 total
Jan 21 - Jan 22
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Glad it is being relaxing to follow nye night! Room comfortable to serve to sleep and lounge

Reviewed on Jan 1, 2026

Quality Inn Oneonta Cooperstown Area
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23 Windham NY
$217 nightly
The price is $234 total per night from Jan 28 to Jan 29
$234 total
Jan 28 - Jan 29
Total with taxes and fees
9.2/10 Wonderful! (81 reviews)
This is one of the most amazing weekend vacations I have been on. I can’t complain about anything!

Reviewed on Jan 5, 2026

Eastwind Windham
See all 1,227 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.

Find the Best Stamford Vacation Packages

Stamford Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
25ºF
Max Temp Summer
75ºF

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Frequently asked questions

How much does a Stamford vacation package cost?
Offering excellent value package deals from $661 on Expedia, you'll be thrilled with how little a vacation to Stamford costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Stamford?
You can usually find lower rates and greater availability in September, November and December. Browse our cheap Stamford vacation packages and you could score some great off-season deals.
How many days is enough for Stamford?
The ideal duration of your Stamford vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to hit all the leading attractions and discover some hidden gems along the way.
How to find the best Stamford package deals?
Begin your search for a Stamford package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Stamford package deal right away, just tweak 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 off to a flying start.
Is it cheaper to book a Stamford vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Stamford vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Stamford?
If you've got your Stamford vacation dates locked in, book early to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Stamford?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Stamford.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodations will probably be the largest expense during your trip to Stamford.
  3. Organize your Stamford getaway with our trip planning tool: Search for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Stamford together.
  4. Work out your trip length: Think about how long you want to spend discovering Stamford. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  5. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Stamford vacation package for you.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the exciting things to do in Stamford and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Stamford vacation packages?
Your Stamford trip is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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