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Philipstown Vacation Rentals

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Our top choices for Philipstown vacation rentals

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
$171 nightly
The price is $185
Jul 6 - Jul 7
Total with taxes and fees
Welcome to Sweet Abby Rose!

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$207 nightly
The price is $234
Jul 13 - Jul 14
Total with taxes and fees
Historic Cabin with Pool & Fire Pit

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
$169 nightly
The price is $200
Jul 7 - Jul 8
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
$280 nightly
The price is $331
Jul 6 - Jul 7
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
$239 nightly
The price is $282
Jul 6 - Jul 7
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
$180 nightly
The price is $204
Jul 8 - Jul 9
Total with taxes and fees
Hoppy Hill Farm House

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (85 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
$208 nightly
The price is $233
Jul 20 - Jul 21
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
$376 nightly
The price is $399
Jul 8 - Jul 9
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$365 nightly
The price is $408
Jul 7 - Jul 8
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
$256 nightly
The price is $277
Jul 6 - Jul 7
Total with taxes and fees
The Tipsy Gypsy - Studio Apartment

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
$261 nightly
The price is $295
Jul 13 - Jul 14
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (15 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$392 nightly
The price is $425
Jul 7 - Jul 8
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$226 nightly
The price is $248
Jul 7 - Jul 8
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
$330 nightly
The price is $358
Jul 9 - Jul 10
Total with taxes and fees
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
$175 nightly
The price is $198
Jul 6 - Jul 7
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (92 reviews)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
$261 nightly
The price is $298
Jul 6 - Jul 7
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$434 nightly
The price is $484
Jul 7 - Jul 8
Total with taxes and fees
Fabulous 3bdrm Home w/parking!

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
$457 nightly
The price is $517
Jul 19 - Jul 20
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (70 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$266 nightly
The price is $314
Jul 7 - Jul 8
Total with taxes and fees
Cozy country efficiency in the Hudson Valley

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
$431 nightly
The price is $488
Jul 6 - Jul 7
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
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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Top Philipstown Hotel Reviews

Find out more about Philipstown

Everything you need to know about Philipstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Philipstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Philipstown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Philipstown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Philipstown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Philipstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Philipstown rentals

At Expedia, we put the best Philipstown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Philipstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Philipstown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Philipstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Philipstown?

Yes, we offer vacation rentals in Philipstown near Garrison Art Center, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Philipstown?

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town: Visitors like this Philipstown vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Philipstown?

Choose from 26 Expedia vacation rentals in Philipstown for a memorable vacation.

What can I see and do in Philipstown?

Enjoy the outdoors at Boscobel House and Gardens and Hudson Highlands State Park, or simply take in cultural attractions like Manitoga The Russel Wright Design Center and Putnam History Museum. Other places in town to visit include Graymoor - The Holy Mountain and Clarence Fahnestock State Park.

What’s a vacation rental in Philipstown like?

Vacation rentals are private properties you can stay in for short or long periods in Philipstown. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family gatherings.