Philipstown Vacation Packages
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Your Philipstown Vacation
Save time and energy on your travel planning by booking a Philipstown vacation package. A great neighborhood to base yourself in this fascinating city is Montrose, which is great for walking and plenty more. Fill up your itinerary with visits to Hudson Highlands State Park, Oscawana Lake and Boscobel House and Gardens, some of the attractions you just have to see during your trip to Philipstown. Don't delay your visit to this city any longer. Your perfect Philipstown vacation is a few quick clicks away with Expedia.
Top Philipstown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $991
per person
Jan 11 - Jan 15
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.
Reviewed on Oct 25, 2026
Eurostars Wall Street
Manhattan
CA $1,570
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
It is definitely older, Only 1 elevator was working, The fan was not working in the bathroom. The floors in the rooms need replacing as the vinyl flooring was peeling up. The bedding and heating was fine. But definitely not worth the 732.00 per night I paid.
Reviewed on Oct 24, 2026
Ready to book your vacation to Philipstown?
Philipstown Hotel Deals
Countryside Motel
3577 Route 9 Cold Spring NY
Fully refundableReserve now, pay when you stay
CA $133
CA $144 total
Oct 27 - Oct 28
includes taxes & fees
7.2/10 Good! (306 reviews)
"Staff was great hotel was dated. Small but clean. Could use counter space in the bathroom. No ac or thermostat but it was warm considering it was cold out. Heat unit was louder than expected but not bad. Decent accommodation considering the price."
Reviewed on Oct 24, 2026
West Gate Inn Nyack
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
CA $139
CA $159 total
Nov 9 - Nov 10
includes taxes & fees
7.4/10 Good! (1,497 reviews)
"Nothing. The room was dirty & the bed had bed bugs. I checked out after being there just over two hours. Management couldn’t give me a different room ( not that I would taken it given the condition of the first room) They wanted to charge me for the full 3 days. I got them to bring it down to one ..."
Reviewed on Oct 25, 2026
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
CA $148
CA $175 total
Nov 2 - Nov 3
includes taxes & fees
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 Philipstown attractions
Boscobel House and Gardens
8.8/10 (5 reviews)
You can spend time exploring the galleries in Boscobel House and Gardens during your trip to Philipstown. Stroll along the riverfront or discover the area's mountain views.
Little Stony Point Park
8.0/10 (3 reviews)
Enjoy the mountain views and explore Little Stony Point Park, a lovely green space in Philipstown. Amble around the area's riverfront or attend a sporting event.
Manitoga The Russel Wright Design Center
You can spend an afternoon exploring the galleries in Manitoga The Russel Wright Design Center during your trip to Philipstown. While you're in the area, stroll along the lakeside.
Putnam History Museum
4.0/10 (1 review)
You can study the exhibits at Putnam History Museum, a museum with a story of its own, during your travels to Philipstown. Wander the riverfront or discover the area's mountain views.
Constitution Marsh Audubon Center and Sanctuary
7.0/10 (2 reviews)
Enjoy the collegiate vibe when you visit Constitution Marsh Audubon Center and Sanctuary, during your travels in Philipstown. Stroll along the riverfront or attend a sporting event in the area.
Graymoor - The Holy Mountain
Learn about the local history of Philipstown when you spend time at Graymoor - The Holy Mountain. While you're in the area, stroll along the riverfront.
Chapel Restoration
8.0/10 (2 reviews)
You can learn about the history of Philipstown with a visit to Chapel Restoration. Stroll along the riverfront or discover the area's mountain views.
West Point Foundry Preserve
9.6/10 (7 reviews)
Learn about the local history of Philipstown when you take a trip to West Point Foundry Preserve. Stroll along the riverfront or attend a sporting event in the area.
What to do in Philipstown
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
CA $1,091
per traveller
Frequently asked questions
How much does a Philipstown vacation package cost?
You can snap up a vacation package to this destination from CA $907 on Expedia. However, how much your vacation to Philipstown costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Philipstown?
January, March and December are great times to look for cheap Philipstown vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Philipstown?
With about 2 days, you'll have enough time to experience popular neighbourhoods such as Vails Gate and Firthcliffe during your Philipstown vacation. Remember to also add Oscawana Lake and Boscobel House and Gardens to your list of must-sees. Searching for more adventures? Consider exploring outside of Philipstown on tours and day trips.
How to find the best Philipstown package deals?
Use Expedia's handy filters to help you find some unbeatable Philipstown package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Philipstown package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Philipstown vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can customize your Philipstown trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Philipstown?
If you have your Philipstown travel dates locked in, book early to snap up some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Philipstown?
- Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to visit Philipstown.
- Budget wisely: As well as the cost of your hotel, you'll need to consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Philipstown.
- Work out your trip length: Consider how long you want to spend discovering Philipstown. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Philipstown vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
