Cragsmoor Vacations from $395

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Your Cragsmoor Vacation

Take the hard work out of travel planning by booking a Cragsmoor vacation package. A good neighborhood to base yourself in this vibrant city is Greenfield Park, which is great for camping and more. Make your trip to Cragsmoor even more fun and exciting by going sightseeing. Sams Point Preserve, Stony Kill Falls and VerKeerderkill Falls are some of the top attractions you'll want to explore. Don't put off your visit to this city any longer. The perfect Cragsmoor vacation is only a few clicks away with Expedia.

The Latest Cragsmoor vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $756, price is now $395 per person
$395
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The compressor from the heat pump in the room was so loud it would wake me up every time it kicked on all night long

Reviewed on Jan 17, 2026

Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Manhattan
Price was $2,647, price is now $693 per person
$693
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (793 reviews)
No frills but good location and meets all the needs.

Reviewed on Jan 4, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,261, price is now $644 per person
$644
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Everything was great!! I even liked the scent so much I bought it!!

Reviewed on Jan 18, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,363, price is now $714 per person
$714
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
convenient, good options

Reviewed on Jan 17, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,875, price is now $1,571 per person
$1,571
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
You need more dinner options in hotel

Reviewed on Jan 17, 2026

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Discover the most popular places to visit in Cragsmoor

Sam's Point Preserve

Explore the great outdoors at Sam's Point Preserve, a lovely green space in Cragsmoor. Wander the forest or discover the mountain views in this relaxing area.

Sam's Point Preserve

Cragsmoor Hotel Deals

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive Monticello NY
$218 nightly
The price is $247 total per night from Jan 22 to Jan 23
$247 total
Jan 22 - Jan 23
Total with taxes and fees
8/10 Very Good! (1,915 reviews)
Pool was fun perfect for my 8 year olds and 4 year old. Breakfast was not included and WAY to expensive in the hotel

Reviewed on Jan 16, 2026

The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive Monticello NY
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $205 total per night from Jan 19 to Jan 20
$205 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (1,116 reviews)
Clean room with a great view.

Reviewed on Jan 15, 2026

Resorts World Catskills Casino
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$94 nightly
The price is $111 total per night from Feb 15 to Feb 16
$111 total
Feb 15 - Feb 16
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Excellent

Reviewed on Jan 17, 2026

Sleep Inn & Suites Middletown - Goshen
See all 894 properties in Cragsmoor
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 Cragsmoor Vacation Packages

Cragsmoor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
450
Top Sights
Lake Minnewaska Beach, Robibero Winery and VerKeerderkill Falls

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Frequently asked questions

How much does a Cragsmoor vacation package cost?
You'll find cheap prices from $395 on Expedia for your Cragsmoor break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cragsmoor costs.
What are the cheapest months to go to Cragsmoor?
You can usually find reduced prices and better availability in November, December and January. Check out our cheap Cragsmoor vacation packages and you could land some great off-season deals.
How many days is enough for Cragsmoor?
Generally, a handful of days is enough to tick off the major attractions during your Cragsmoor vacation. But if you want to have time to kick back or go on day tours, think about extending your itinerary.
How to find the best Cragsmoor package deals?
Use Expedia's handy filters to find some fabulous Cragsmoor package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Cragsmoor package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Cragsmoor vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a tailored Cragsmoor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Cragsmoor?
If you've got your Cragsmoor travel dates confirmed, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Cragsmoor vacation packages?
Your Cragsmoor getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little 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 spread the cost over 3, 6 or 12 months. Plus, there are no hidden 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.