Vacation rentals in Philipstown

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Top-rated vacation rentals in Philipstown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Home in Philipstown

4.92 out of 5 average rating, 110 reviews

Cozy 3 bedroom house on quiet private road

3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahnestock State Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $75 per stay. I live close by so I’m available for help or assistance during your stay.

May 1 – 8

$397 CAD per night
Superhost

Apartment in Philipstown

4.88 out of 5 average rating, 183 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Jun. 13 – 20

$208 CAD per night
Guest favourite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Jan. 16 – 23

$789 CAD per night

Popular amenities for Philipstown vacation rentals

Stay near Philipstown's top sights

The Thayer Hotel15 locals recommend
United States Military Academy58 locals recommend
Boscobel House and Gardens96 locals recommend
West Point Academy60 locals recommend
Cold Spring Depot22 locals recommend
Madam Brett Park45 locals recommend

Other great vacation rentals in Philipstown

Guest favourite

Home in Cold Spring

4.95 out of 5 average rating, 278 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Sep. 18 – 25

$657 CAD per night
Guest favourite

Apartment in Beacon

4.91 out of 5 average rating, 502 reviews

Cozy Beacon Studio

Sep. 10 – 17

$190 CAD per night
Guest favourite

Guest suite in Beacon

4.94 out of 5 average rating, 235 reviews

Quiet apartment with garden access, mountain views

Jul. 24 – 31

$208 CAD per night
Guest favourite

Home in Highland Falls

4.88 out of 5 average rating, 144 reviews

Luxury Townhouse Near West Point

Apr. 15 – 22

$255 CAD per night
Guest favourite

Guest suite in Putnam Valley

4.9 out of 5 average rating, 30 reviews

Peaceful lake and woodland retreat

Aug. 31 – Sep. 7

$148 CAD per night
Guest favourite

Guesthouse in Philipstown

5.0 out of 5 average rating, 32 reviews

Historic 1 bedroom home in Cold Spring, NY

Jan. 31 – Feb. 7

$352 CAD per night
Guest favourite

Guesthouse in Cold Spring

4.99 out of 5 average rating, 89 reviews

Bright/modern forest escape. Near village & train

Nov. 18 – 25

$197 CAD per night
Guest favourite

Home in Mohegan Lake

4.97 out of 5 average rating, 29 reviews

A nice place to getaway

Nov. 21 – 28

$168 CAD per night
Guest favourite

Apartment in Highland Falls

4.84 out of 5 average rating, 95 reviews

Cozy 1-bedroom retreat minutes from West Point!

Jul. 14 – 21

$170 CAD per night
Guest favourite

Home in Philipstown

5.0 out of 5 average rating, 13 reviews

Modern Cottage in the Woods, Garrison

Apr. 30 – May 7

$648 CAD per night
Guest favourite

Guest suite in Highland Falls

4.94 out of 5 average rating, 31 reviews

Modern place with private gated parking.

Jan. 27 – Feb. 3

$173 CAD per night
Guest favourite

Cabin in Philipstown

5.0 out of 5 average rating, 6 reviews

Romantic Cottage with a Sunset View

Apr. 5 – 12

$367 CAD per night

Quick stats about vacation rentals in Philipstown

Total rentals

340 properties

Rentals with dedicated workspaces

190 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

110 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

17K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Putnam County
  5. Philipstown