Philipstown Vacation Packages

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Photo by Bibek Magar

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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.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $1,833, price is now CA $1,106 per person
CA $1,106
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,486, price is now CA $1,336 per person
CA $1,336
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $2,413, price is now CA $1,539 per person
CA $1,539
per person
Jan 13 - Jan 20
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

Ready to book your vacation to Philipstown?

 

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Philipstown Hotel Deals

West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Nov 10 to Nov 11
CA $153
CA $175 total
Nov 10 - Nov 11
includes taxes & fees
7.4/10 Good! (1,513 reviews)
"Everything was good, but the wifi was not that great in the room"

Reviewed on Nov 6, 2026

West Gate Inn Nyack
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Nov 15 to Nov 16
CA $167
CA $229 total
Nov 15 - Nov 16
includes taxes & fees
Hotel Nyack, a JdV by Hyatt Hotel
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
The price is CA $150 per night from Nov 10 to Nov 11
CA $150
CA $177 total
Nov 10 - Nov 11
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"We were in line waiting for check in and a woman took about 30 minutes with the only gentleman at the desk. There was a line out the door. We got our first room and it smelled horribly like mildew and dampness. Went back to the check in area and we were given a new room. It was definitely not an ..."

Reviewed on Nov 6, 2026

Overlook Lodge at Bear Mountain
See all 995 properties in Philipstown
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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Stay near popular Philipstown attractions

A river winding through a green landscape with hills in the background.

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.
See properties

What to do in Philipstown

7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

CA $1,100
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in Philipstown

Frequently asked questions

How much does a Philipstown vacation package cost?
You can snap up a vacation package to this destination from CA $1,106 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.