Stamford Vacations from $504

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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.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Save 100% on your flight
Price was $703, price is now $504 per person
$504
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9.2/10 Wonderful! (266 reviews)
The staff was incredible and so helpful!! I can honestly say I haven't had such super customer service as we experienced here! Thank you

Reviewed on Aug 22, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $933, price is now $628 per person
$628
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9/10 Wonderful! (411 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

The Hidden Inn

The Hidden Inn

4 out of 5
Save 100% on your flight
Price was $870, price is now $628 per person
$628
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (37 reviews)
The staff was great. There has to be a better communication between the hotel and expedia.

Reviewed on Aug 20, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,631, price is now $1,200 per person
$1,200
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
9.4/10 Exceptional! (170 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.

Reviewed on Aug 18, 2025

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Save 100% on your flight
Price was $782, price is now $610 per person
$610
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.2/10 Wonderful! (737 reviews)
Comfortable, clean room. Beautiful surroundings. Friendly, helpful staff.

Reviewed on Aug 23, 2025

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Stamford Hotel Deals

The Vine on main

The Vine on main

2 out of 5
105 Main St, Stamford, NY
$207 nightly
The price is $228 total per night from Sep 3 to Sep 4
$228 total
Sep 3 - Sep 4
Total with taxes and fees
7.8/10 Good! (84 reviews)
"The property is clean. The rates were good. It was very convenient to Cooperstown for the Hall of Fame Induction weekend. My husband really liked the shower amenities-- both the shower head and the Trader Joe's 3-in-1 soap. We enjoyed dinner at the Mill Pond in Jefferson. And the Fire Department ..."

Reviewed on Jul 28, 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
$134 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (620 reviews)
"Beautiful property. Lovely room with a very comfortable bed. Extremely helpful desk staff—I would like to extend my thanks especially to her."

Reviewed on Aug 20, 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
$105 nightly
The price is $120 total per night from Sep 10 to Sep 11
$120 total
Sep 10 - Sep 11
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"Good"

Reviewed on Aug 20, 2025

Quality Inn Oneonta Cooperstown Area
See all 1,247 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.

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Frequently asked questions

How much does a Stamford vacation package cost?
Offering excellent value package deals from $504 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.