Vacation rentals in Garrison, Philipstown

A fire pit surrounded by large stones is illuminated by a warm fire, creating a cozy gathering space. Trees gently rise in the background, with soft lighting from the house visible nearby. The scene conveys a tranquil nighttime atmosphere, inviting relaxation and reflection.

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

A wooden deck with a railing covered in climbing plants overlooks a garden area. Potted flowers in vibrant colors are arranged on the deck. The background features a well-tended garden with seating arrangements and lush greenery, creating a serene outdoor setting.

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.

4.99 out of 5 average rating, 196 reviews

A panoramic view of a river valley is captured from a vantage point. A suspension bridge spans the water below, surrounded by lush hills and trees with emerging green foliage. Two individuals are seated, taking in the natural beauty of the landscape.

Cottage in Cortlandt

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

4.94 out of 5 average rating, 256 reviews

The interior of a wooden sauna is shown, featuring warm cedar walls and benches. A stove is located at the center, surrounded by two folding chairs and neatly rolled green towels. A wooden bucket sits in one corner, emphasizing the tranquil spa environment.

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

4.87 out of 5 average rating, 415 reviews

A historical stone structure is seen on an island surrounded by colorful autumn foliage. The building features intricate architectural details and towers, while the calm waters of the river reflect the vibrant colors of the trees. Distant mountains form a subtle backdrop.

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.

4.99 out of 5 average rating, 106 reviews

Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

4.94 out of 5 average rating, 126 reviews

A spacious deck is visible, featuring a grill and a small dining set, which includes two chairs and a table. The entrance to the house is framed by steps leading up from the deck. Lush greenery surrounds the property, enhancing the tranquil setting.

Home in Cold Spring

Peaceful Yellow Door Cottage

Yellow Door Cottage is a quiet family getaway nestled in the woods, but close to the historic Village of Cold Spring. Large backyard, ideal for afternoon lunch on the deck or an evening around the fire. Located on a lovely country road, great for walking and biking. 3 comfy bedrooms with linens supplied. Wi-Fi, TVs, washer/dryer, close to amazing hikes and the beautiful Hudson River! Rent alone or pair with my cottage next door: Cheerful Private 3 Bedroom Cottage in Cold Spring on Airbnb.

4.86 out of 5 average rating, 188 reviews

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guesthouse in Cold Spring

A tranquil gravel road lined with lush green trees stretches into the distance. Natural stone borders are visible along the edge of the pathway, providing a rustic charm. Soft light filters through the leaves, creating a serene and inviting ambiance.

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.

4.95 out of 5 average rating, 170 reviews

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

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, 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.

4.99 out of 5 average rating, 312 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

4.92 out of 5 average rating, 276 reviews

The nighttime image showcases the illuminated marquee of the Paramount Theater, featuring vibrant lights and signage. A crowd gathers outside, with classic cars parked along the street. The architecture of the theater is highlighted against the dark sky, enhancing its vintage charm.

Guesthouse in Peekskill

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

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Popular amenities for Garrison, Philipstown vacation rentals

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Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Garrison, Philipstown

A sunroom featuring large glass doors offers views of the river and surrounding greenery. Two wicker chairs are positioned next to a small table, creating a cozy seating area. Soft fairy lights are arranged along the ceiling, enhancing the inviting atmosphere.

4.73 out of 5 average rating, 150 reviews

Bungalow near West Point on Hudson River

AmyRating, 5 stars4 weeks ago

This was our second stay with Laura and it was wonderful again. The location is very convenient if you are traveling to West Point. The view from the backyard and sunroom is amazing. Yes, there is train noise but it didn't bother us. We will stay here again.

4.91 out of 5 average rating, 55 reviews

A wood-burning stove is positioned on a wooden floor, emitting a warm glow from its front glass doors. The stove is surrounded by a sleek, black heat shield and complemented by neatly stacked firewood nearby. A stylish black fireplace tool holder stands beside the stove.

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

A cascading waterfall flows over rocky terrain into a serene pool, surrounded by lush green foliage. The natural setting offers a peaceful ambiance, with light filtering through the vibrant leaves overhead, creating dappled shadows on the water and stones below.

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.

4.92 out of 5 average rating, 37 reviews

A well-appointed kitchen is revealed through a large garden window, showcasing views of a snowy landscape. A sink is positioned below the window, accompanied by a countertop with a fruit bowl containing bananas. Nearby, a stand mixer and a potted plant are visible.

Home in Fort Montgomery

West Point Cottage

SamanthaRating, 5 stars2 weeks ago

My partner and I booked Philomena and Derek’s place for Memorial Day wknd to attend a wedding at West Point. It was the perfect location and a cute space. We went to dinner at a restaurant nearby called the Bird and Bottle Inn which was also great.

4.82 out of 5 average rating, 57 reviews

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More

StacyRating, 5 stars1 month ago

Claudine’s place was great for a quick get away from the city. The place was cozy and spacious at the same time. The pool, hot tub and labyrinth have the property that extra special touch. Claudine herself was super responsive, friendly and helpful. Would definitely recommend

A cozy fire pit is surrounded by a circle of natural stones, set on a grassy area. The fire pit features a metal framework and is situated among small plants and scattered stones, creating an inviting outdoor gathering space.

5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars6 months ago

There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)