Castle Point Vacations from $330

Book a Hotel + Flight or Car together to unlock savings

Your Castle Point Vacation

Say farewell to the hassle of planning and hello to a Castle Point vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Poughkeepsie Waterfront, which is great for families, history and culture. Any trip to Castle Point needs a well-crafted itinerary. Fill yours with leading attractions like Poughkeepsie Galleria, Bowdoin Park and Dutchess Stadium. No matter your travel plans or the size of your budget, putting together a tailored Castle Point vacation is a cinch with Expedia.

The Latest Castle Point vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was $519, price is now $330 per person
$330
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (8,157 reviews)
Location location location! No-frills hotel right off of Times Square with large rooms (for Manhattan). Building is showing its age but doesn't feel dirty or run down. I'd call it "charming". Heating/AC unit is very noisy. Elevators can get crowded at checkout time.

Reviewed on Nov 12, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was $1,728, price is now $1,000 per person
$1,000
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $1,548, price is now $938 per person
$938
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $3,635, price is now $2,246 per person
$2,246
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Our servis was excellent. Maria is the best staff, so helpfully and really nice so I could take she with me home 😊

Reviewed on Nov 11, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $2,007, price is now $1,275 per person
$1,275
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Great for a date night getaway . Staff was kind and helpful. Would definitely stay again.

Reviewed on Nov 11, 2026

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Castle Point Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $109 total per night from Dec 13 to Dec 14
$109 total
Dec 13 - Dec 14
Total with taxes and fees
9/10 Wonderful! (1,165 reviews)
"Wonderful breakfast! Beautiful, clean room! Will stay here again!!!"

Reviewed on Nov 12, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $125 total per night from Nov 22 to Nov 23
$125 total
Nov 22 - Nov 23
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"We had to wait two hours and a half for our dinner in the large hall. Not even tells us why it took so long."

Reviewed on Nov 12, 2026

Overlook Lodge at Bear Mountain
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
$104 nightly
The price is $120 total per night from Nov 29 to Nov 30
$120 total
Nov 29 - Nov 30
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Super helpful and accommodating! Def recommend."

Reviewed on Nov 12, 2026

Comfort Suites Fishkill near Interstate 84
See all 751 properties in Castle Point
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 Castle Point Vacation Packages

Castle Point Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Top Sights
Fun Central, Dutchess Stadium and Bowdoin Park

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Frequently asked questions

How much does a Castle Point vacation package cost?
You'll find cheap prices from $330 on Expedia for your Castle Point escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Castle Point costs.
What are the cheapest months to go to Castle Point?
December, January and February are the best times to search for cheap Castle Point vacation packages. Choosing to travel in less busy periods means you can typically find better prices on accommodations and flights.
How many days is enough for Castle Point?
With a well-planned itinerary, you can easily hit the main Castle Point attractions in a handful of days. But if you want to venture off the beaten track or take day trips, think about booking your Castle Point vacation for longer.
How to find the best Castle Point package deals?
Use Expedia's filters to help you find some terrific Castle Point package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Castle Point package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Castle Point vacation as a package?
You can enjoy significant savings on your next Castle Point break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Castle Point?
Secure incredible discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Castle Point break.
Does Expedia offer Book Now, Pay Later Castle Point vacation packages?
Your Castle Point trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden 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.