Philipstown Vacations from $366

Book a Hotel + Flight or Car together to unlock savings

Photo by Kiri Romero

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.

The Latest Philipstown 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 $712, price is now $366 per person
$366
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
The hotel itself was nice. There is truly nothing but senior citizens that stay here. We walked in and thought it was a nursing home. I’m not joking there must have been at least 60 70year olds when we walked in. They just take over the entire hotel. Again, the hotel itself is nice, but I think we would stay somewhere else knowing what we know now especially with two teenage boys with us.

Reviewed on Aug 28, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,480, price is now $1,630 per person
$1,630
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,005 reviews)
Great hotel. Small rooms

Reviewed on Aug 31, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,404, price is now $1,302 per person
$1,302
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Everyone was helpful and super friendly.

Reviewed on Aug 28, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,754, price is now $974 per person
$974
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,303 reviews)
Solid Marriott but a few design issues-oddly our unit was noticeably underlighted with no ceiling light near door and closet and much too dim in-mirror lighting in bathroom. Also, oddly, no full length mirror in unit. But very clean unit with helpful staff and attractive dining and fitness level.

Reviewed on Sep 1, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,461, price is now $815 per person
$815
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (563 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound

Reviewed on Aug 18, 2025

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Discover the most popular places to visit in Philipstown

Beautiful little gem of a garden in Putnam County, New York State. #Patterns

Stonecrop Gardens

Enjoy the mountain views and explore Stonecrop Gardens, a lovely green space in Philipstown. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Stonecrop Gardens

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.

Manitoga The Russel Wright Design Center

Boscobel House and Gardens

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.

Boscobel House and Gardens

What to do in Philipstown

Guided Shared Group Forest Bathing Session in Serene Woodland Park

Guided Shared Group Forest Bathing Session in Serene Woodland Park

$40
per adult
Guided Shared Group Forest Bathing Session in Serene Woodland Park
New York Thift, Outlet, and Consignment Shopping Tour

NY Thrift Shopping & Wine Tour

$399
per adult
NY Thrift Shopping & Wine Tour
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

$133
per adult
Beacon: Gourmet Beacon Food Tour
See all activities in Philipstown

Philipstown Hotel Deals

Countryside Motel

Countryside Motel

2 out of 5
3577 Route 9, Cold Spring, NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $103 total per night from Sep 2 to Sep 3
$103 total
Sep 2 - Sep 3
Total with taxes and fees
Countryside Motel
Cold Spring Hotel

Cold Spring Hotel

3 out of 5
124 Main St., Cold Spring, NY
$202 nightly
The price is $218 total per night from Sep 8 to Sep 9
$218 total
Sep 8 - Sep 9
Total with taxes and fees
Cold Spring Hotel
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $164 total per night from Sep 7 to Sep 8
$164 total
Sep 7 - Sep 8
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
See all 932 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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Frequently asked questions

How much does a Philipstown vacation package cost?
Offering great value package deals from $366 on Expedia, you'll be surprised at how little a vacation to Philipstown costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Philipstown?
If you're hoping to snag a cheap Philipstown vacation package, consider visiting in December, January and February. You'll usually find better rates on flights and accommodations during these months — perfect for travelers wishing to save money.
How many days is enough for Philipstown?
With a well-planned itinerary, you can easily visit the most popular Philipstown sights in a handful of days. But if you want to discover lesser-known spots or take day trips, consider booking your Philipstown vacation for longer.
How to find the best Philipstown package deals?
Start your search for a Philipstown package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor 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 perfect Philipstown package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Philipstown getaway off to a flying start.
Is it cheaper to book a Philipstown vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can tailor your Philipstown trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Philipstown?
If you've got your Philipstown vacation dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Philipstown?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Philipstown.
  2. Set a budget: Consider costs such as transportation, flights and meals when working out how much to put aside for your trip to Philipstown. Then, select a property that suits your budget, whether that's a low-cost stay or a lavish getaway.
  3. Use Expedia's trip planning tool to discover Philipstown: Research every part of your trip to Philipstown with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go away for: Now that you're more familiar with Philipstown, you can figure out the ideal length of your break. Create a rough plan and give yourself enough time to cover everything you want to do.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Philipstown vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our travel guide to find some fun things to do in Philipstown in Philipstown. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Philipstown vacation packages?
Secure your dream escape to Philipstown with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.