Holiday houses in Philipstown

4.93 out of 5 average rating, 131 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 $80 per stay. I live close by so I’m available for help or assistance during your stay.

4.91 out of 5 average rating, 232 reviews

Apartment in Philipstown

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.

4.94 out of 5 average rating, 256 reviews

Apartment in Cold Spring

HOT Sauna - Mountain Views - Hiking - NYC Trains

Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

4.94 out of 5 average rating, 140 reviews

Cottage in Cold Spring

Cheerful Private 3 Bedroom Cottage in Cold Spring

Relax with friends & family at this peaceful forrest cottage, just 7-minutes outside of The Historic Village of Cold Spring on a beautiful, quiet country road. Much bigger on the inside than it looks, this place has what you need: fresh linens, full kitchen, wifi, streaming tvs and plenty of great books to read. There is a trampoline in the backyard & patio lights for Spring/Summer/Fall nights dining outside. Rent alone or pair with my cottage next door: Peaceful Yellow Door Cottage on Airbnb.

4.87 out of 5 average rating, 415 reviews

Apartment in Cold Spring

Idyllic! Just steps from Main Street!

Private and quiet, cozy two bedroom apartment in the center of the Village. You’ll feel as if you are a world away, with access to our private Garden and Koi Pond. Just a 7 minute walk to and from the Metro North train. Within walking distance to everything: shopping, Fine or Casual dining, our Hudson River dock, hiking trails (Breakneck Ridge and others), even a supermarket, drug store, and post office! Off street parking for 1 automobile, and free on street parking Mondays through Thursdays.

4.95 out of 5 average rating, 233 reviews

Guesthouse in Mahopac

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

4.94 out of 5 average rating, 128 reviews

Cabin in Putnam Valley

Sweet, stylish cabin in the woods- hiking & more!

Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Guesthouse in Cold Spring

4.99 out of 5 average rating, 164 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.96 out of 5 average rating, 111 reviews

Guest suite in Cornwall

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

5 out of 5 average rating, 286 reviews

Tiny home in Cold Spring

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.

4.99 out of 5 average rating, 202 reviews

Cottage in Philipstown

Modern Country Cottage by Bear Mountain

Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

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Other great holiday rentals in Philipstown

4.92 out of 5 average rating, 204 reviews

The Garrison Cottage

LauraRating, 5 stars3 weeks ago

We absolutely loved this cozy home away from home. The deck and view are amazing. There was plenty of room for our whole family to enjoy a long meal. All the appliances work great and the beds and bedding are very comfortable. We hope to come back every year!

4.91 out of 5 average rating, 55 reviews

Home in Cold Spring

Summer Adventures in Cold Spring at Gilbo's

BillRating, 5 stars2 weeks ago

We were there for a USMA graduation, and the location / accommodations worked great. Handy having a decent grocery store two blocks away. The walking loop down to the Foundry and Cold Springs Park is delightful. Nice with our house guests (extended family and friends) to be able to spread out in the place. Kitchen was spacious and awesome for family meals. Pool wasn't open yet, but looked inviting to add to the outside BBQ area.

4.87 out of 5 average rating, 30 reviews

Apartment in Garrison

Private Apartment in 1820’s Cottage - New Reno

CharleneRating, 5 stars5 months ago

We had a great stay at Samara's apartment/cottage over Christmas. The location was perfect since we were visiting with family in Cold Spring, and it was wonderful to have a quiet and beautiful spot as home base. We're grateful to have hosts with pet-friendly accommodations, being able to bring our 2 dogs makes travel possible, and this location was perfect for them. The space was clean, quiet and we felt very at home there. It's a thrill to walk into a location and smell nothing - as in, not musty, not smelling like strong cleaning products - just neutral, fresh air. The bed was so cozy and comfy, and the kitchen had everything we needed. Samara was very responsive to a few questions I had before we made our reservation, and was easy to text with when we were staying there. We look forward to our next visit!

5 out of 5 average rating, 10 reviews

Home in Putnam Valley

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago

After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

4.94 out of 5 average rating, 112 reviews

Hikers retreat in the Hudson Valley

AasmundRating, 5 stars9 months ago

Wonderful place, wonderful hosts, loved it!!

5 out of 5 average rating, 35 reviews

Home in Cold Spring

Home in Cold Spring- Farm Stay!

BeckyRating, 5 stars3 weeks ago

Beautiful home, designed and decorated with such thoughtfulness. Cheryl&Jamie were very generous, providing us with farm fresh eggs, snacks and carrots for the animals. The house was fully equipped with games, kitchen supplies, towels etc. Drivable to many towns. We are already planning for our next trip here.

4.79 out of 5 average rating, 227 reviews

Cottage in Cold Spring

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

SandraRating, 5 stars2 weeks ago

Our 2nd stay with this host. They are so caring & go above & beyond to make sure our stay is great. The house is super cute & very spacious. It’s very quiet & the huge yard is not only gorgeous but the perfect size for our dog. I wish I would have remembered there is a great big jacuzzi. I book my trip to Cold Spring around their availability. I highly recommend!!