Vacation rentals in Philipstown

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Top-rated vacation rentals in Philipstown

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Guest favorite

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.

Aug 27 – Sep 3

ﺩ.ﺇ1,035 per night

Guest favorite

Apartment in Philipstown

4.88 out of 5 average rating, 188 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.

Sep 9 – 16

ﺩ.ﺇ491 per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 160 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep 29 – Oct 6

ﺩ.ﺇ490 per night

Guest favorite

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.

Oct 25 – Nov 1

ﺩ.ﺇ2,027 per night

Guest favorite

Guest suite in Beacon

4.97 out of 5 average rating, 290 reviews

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

ﺩ.ﺇ367 per night

Guest favorite

Guest suite in Cold Spring

4.79 out of 5 average rating, 484 reviews

Cozy getaway in Cold Spring

Sweet studio attached to our house w/updated kitchen & bathroom on a dead-end street backed up to a nature preserve. We have parking for those arriving by car & are a block from the train if coming up from the city. Walking distance to everything (Main St is 2 blocks away!) We welcome all types of folks and your lovely pets as well. We're here for your needs & offer as much contact or privacy as you like! In the summer, an outdoor shower is available to you as well through the backyard.

Feb 20 – 27

ﺩ.ﺇ554 per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 296 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Jan 9 – 16

ﺩ.ﺇ310 per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 113 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Sep 11 – 18

ﺩ.ﺇ462 per night

Guest favorite

Apartment in Beacon

4.99 out of 5 average rating, 487 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Sep 12 – 19

ﺩ.ﺇ686 per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 394 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Aug 8 – 15

ﺩ.ﺇ334 per night

Guest favorite

Tiny home in Cold Spring

5.0 out of 5 average rating, 240 reviews

Tiny house on tiny farm close to hiking trails.

This space is a unique and private dwelling on 5.5 acres of property. The tiny house is a newly renovated modern and artistically designed space. Guests will have access to the back yard and wood lands. There are small trails and sitting areas that guests are free to enjoy. There is also a hiking trail walking distance down the street that leads to the Fishkill Ridge and Beacon.

Jun 3 – 10

ﺩ.ﺇ517 per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 209 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Nov 3 – 10

ﺩ.ﺇ480 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Philipstown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Philipstown's top sights

The Thayer Hotel15 locals recommend

Boscobel House and Gardens96 locals recommend

United States Military Academy58 locals recommend

West Point Academy60 locals recommend

Cold Spring Depot22 locals recommend

Madam Brett Park45 locals recommend

Other great vacation rentals in Philipstown

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 281 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Jan 19 – 26

ﺩ.ﺇ1,697 per night

Guest favorite

Guesthouse in Philipstown

5.0 out of 5 average rating, 38 reviews

Historic 1 bedroom home in Cold Spring, NY

Feb 19 – 26

ﺩ.ﺇ898 per night

Guest favorite

Guesthouse in Cold Spring

4.99 out of 5 average rating, 95 reviews

Bright/modern forest escape. Near village & train

Feb 28 – Mar 7

ﺩ.ﺇ471 per night

Guest favorite

Guest suite in Putnam Valley

4.91 out of 5 average rating, 33 reviews

Peaceful lake and woodland retreat

Sep 21 – 28

ﺩ.ﺇ396 per night

Guest favorite

Home in Highland Falls

4.98 out of 5 average rating, 46 reviews

Luxury Home Near West Point

Apr 6 – 13

ﺩ.ﺇ489 per night

Guest favorite

Guest suite in Putnam Valley

4.99 out of 5 average rating, 85 reviews

Nestled in Nature

Jun 30 – Jul 7

ﺩ.ﺇ514 per night

Guest favorite

Home in Philipstown

5.0 out of 5 average rating, 13 reviews

Modern Cottage in the Woods, Garrison

May 13 – 20

ﺩ.ﺇ1,669 per night

Guest favorite

Guest suite in Highland Falls

4.94 out of 5 average rating, 33 reviews

Modern place with private gated parking.

Sep 4 – 11

ﺩ.ﺇ438 per night

Show all

Quick stats about vacation rentals in Philipstown

Total rentals
340 properties
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
18K reviews

Frequently Asked Questions

Do cottage rentals in Philipstown have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Philipstown have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Philipstown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Bed And Breakfast Rentals in Philipstown?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in rv rentals in Philipstown?
Experience the best of Philipstown with our rv rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Philipstown have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Philipstown?
Philipstown has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Philipstown have free parking?
Absolutely! We offer over 30 apartment rentals with free parking in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Philipstown?
Four-legged friends are welcome in Philipstown. Choose from more than 110 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Philipstown?
Yes! Work meets play with ease at over 200 vacation rentals in Philipstown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Philipstown vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Philipstown, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Philipstown

Top-rated vacation rentals in Philipstown

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Philipstown vacation rentals

Stay near Philipstown's top sights

Other great vacation rentals in Philipstown

Home in Cold Spring

Guesthouse in Philipstown

Guesthouse in Cold Spring

Guest suite in Putnam Valley

Home in Highland Falls

Guest suite in Putnam Valley

Home in Philipstown

Guest suite in Highland Falls

Quick stats about vacation rentals in Philipstown

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do cottage rentals in Philipstown have wifi?

Do cottage rentals in Philipstown have air conditioning?

What are the most popular amenities for Bed And Breakfast Rentals in Philipstown?

How much does it cost to stay in rv rentals in Philipstown?

Do apartment rentals in Philipstown have a kitchen?

Are there family-friendly vacation rentals in Philipstown?

Do apartment rentals in Philipstown have free parking?

Are there pet-friendly vacation rentals in Philipstown?

Are there vacation rentals with a dedicated workspace in Philipstown?

Are there Philipstown vacation rentals on Airbnb with pools?

Destinations to explore