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Philipstown Vacation Rentals

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Vacation Rentals in Philipstown

1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"Very nice. A lot of attention to detail"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is ¥29,043
per night
May 29 - May 30
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (17)
"We really enjoyed staying at this cottage, much better than 2 rooms in a hotel. Very quiet, fully equipped kitchen.Easy to prepare meals when we wished. We visit the Ridgefield area several times per year and will definitely consider staying here again."
Serenity Awaits at this Cozy Lakeside Bungalow
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is ¥17,104
per night
Jun 4 - Jun 5
Cabin in the heart of the Hudson Valley, Cabin 2
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very Good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is ¥17,104
per night
May 29 - May 30
Cabin in the heart of the Hudson Valley, Cabin 4
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is ¥20,243
per night
Jun 19 - Jun 20
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
The price is ¥20,409
per night
May 29 - May 30
Cozy family-friendly home!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"House is very cute. The scenery in early spring was amazing. Very quiet neighborhood. Conveniently located. Very clean. Beds were very comfortable. Had everything we needed."
The price is ¥23,549
per night
May 29 - May 30
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, (4)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is ¥80,029
per night
May 30 - May 31
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Exterior
Mountain View escape
10.0 out of 10, Exceptional, (25)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
Don't see what you're looking for?
See all available 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.

Other types of properties in Philipstown you may be interested in

1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Desk, laptop workspace, blackout drapes, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very Good, (1024)
"We enjoy our stay and everything was very nice. Will definitely stay there again "
The price is ¥19,607
per night
Jun 9 - Jun 10
Baymont by Wyndham White Plains - Elmsford
Lobby sitting area
West Gate Inn Nyack
3.0 star property
7.4 out of 10, Good, (1004)
"We ESPECIALLY loved the banquet breakfast"
The price is ¥15,275
per night
Jun 4 - Jun 5
West Gate Inn Nyack
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

Can I find vacation rentals in Philipstown?

Yes, we offer vacation rentals in Philipstown near Stonecrop Gardens, 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: Visitors like this Philipstown vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Philipstown?

Choose from 32 Expedia vacation rentals in Philipstown for a memorable vacation.

What can I see and do in Philipstown?

Enjoy the outdoors at Hudson Highlands State Park and Clarence Fahnestock State Park, or simply take in cultural attractions like Boscobel House and Gardens and Manitoga The Russel Wright Design Center. Other places in town to visit include Hudson River and West Point Foundry Preserve.

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.

Recent reviews of Philipstown properties
Expedia verified reviews