Vacation rentals in Town of Philipstown

4.91 out of 5 average rating, 237 reviews

The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.

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, 268 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

A lap pool glimmers under natural light, surrounded by lush greenery. Sun loungers and an umbrella are placed on the wooden deck nearby, providing a relaxing space for outdoor enjoyment. The tranquil setting offers a peaceful retreat from the surrounding environment.

4.89 out of 5 average rating, 18 reviews

Charming contemporary cottage with lap pool

Formerly an old schoolhouse, this cottage brings a unique charm and style to the area that even Barbara Streisand enjoyed a stay while filming the acclaimed film, "Hello, Dolly!". With 3 bedrooms, all with Casper mattresses and luxurious linens, up to 5 beds, and 2 full baths, a fully enclosed lush garden w/lap pool, the cottage makes for an easy accessible escape from the city being just one hour north by car or train. Conveniently located between Garrison station and Cold Spring village.

4.95 out of 5 average rating, 130 reviews

A charming cottage is framed by trees, with a welcoming yellow door nestled among the greenery. A stone pathway leads to the entrance, bordered by well-maintained grass. Natural light filters through the surrounding foliage, enhancing the peaceful ambiance of the 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.

Superhost

A charming cabin with a red exterior is nestled among tall trees and autumn foliage. The building features multiple windows and a staircase leading to the entrance, while a rock border surrounds the lush ground cover and fallen leaves.

Cabin in Putnam Valley

4.94 out of 5 average rating, 133 reviews

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

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

4.99 out of 5 average rating, 170 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.

4.92 out of 5 average rating, 210 reviews

A private deck is shown, featuring a blue and white patterned rug, a small table, and two chairs. Surrounding greenery and trees contribute to the serene view, with the Hudson River visible in the background under a cloudy sky.

Guest suite in Newburgh

Hudson River Views-idyllic getaway 75 min. to NYC

Cozy suite with fireplace and private deck views of the majestic Hudson River nestled in a quiet safe residential well-maintained neighborhood away from the city of Newburgh close to the Newburgh-Beacon bridge and the prestigious Powelton Country Club. This suite has a full kitchenette and a separate living space with couch, smart TV, queen bed and table. It has its own deck accessible by a sliding glass door where you can enjoy sunrises and soak in the peaceful views.

Guesthouse in Philipstown

A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.

4.99 out of 5 average rating, 99 reviews

Historic 1 bedroom home in Cold Spring, NY

This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

4.95 out of 5 average rating, 534 reviews

A vintage Airstream camper is nestled among vibrant autumn foliage, featuring shades of red and yellow. Surrounding the camper are rugged stones and a rustic outdoor seating area. The ground is covered in fallen leaves, enhancing the natural ambiance of the wooded setting.

Camper/RV in Cold Spring

Hudson Highlands Base Camp

This vintage beauty is tucked away in the woods, near trail heads for spectacular hikes in the Hudson Highlands. Bull Hill, Breakneck and Mount Beacon are all accessible from here. Yet only a 20 minute walk (uphill) from Cold Spring Metro North station and 10 minutes from all shops. No car needed for this adventure. This 34 ft. land yacht is the perfect retreat. Full kitchen, bath/shower, heat, hot water and WiFi

5 out of 5 average rating, 293 reviews

A charming pink house is surrounded by a white picket fence and lush greenery. Flowering bushes bloom brightly near the home's exterior, while a window framed in lilac enhances the inviting feel of the property. Sunlight casts a warm glow on the vibrant foliage.

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, 204 reviews

A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.

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.

Guest suite in Putnam Valley

A small black table is set with two white cups, accompanied by two black folding chairs. The grassy area opens up to a serene pond, framed by lush trees and greenery, creating a peaceful outdoor setting.

4.99 out of 5 average rating, 124 reviews

Nestled in Nature

Welcome to the Hudson Valley, just an hour from Midtown! We’re situated a few minutes from Fahnestock State Park, scenic Cold Spring, and a revitalized Peekskill! While these and many more attractions are nearby, the peace and serenity of our house and property are a welcome change of pace from the city.

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Popular amenities for Town of Philipstown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Town of Philipstown

An evening deck scene is illuminated by soft string lights, offering a welcoming ambiance. A modern grill sits beside potted plants, with views of trees and distant hills captured against the twilight sky.

4.96 out of 5 average rating, 25 reviews

Tranquil Hudson Valley Retreat with Cedar Hot Tub

A spacious multi-story house is shown, featuring dark wood siding and large windows. A broad staircase leads to an inviting deck with outdoor seating. Lush greenery surrounds the property, while a gravel path guides visitors to a generous wooden table set in the yard.

5 out of 5 average rating, 3 reviews

Nordic escape among tree tops

A charming early century Cape is set on a spacious green lawn. The house features a light-colored exterior with a gabled roof and symmetrically placed windows. Mature trees provide a tranquil backdrop against a clear blue sky.

4.92 out of 5 average rating, 204 reviews

The Garrison Cottage

Guest suite in New Windsor

A bright living area features a cozy gray sofa complemented by two white armchairs with wooden frames. Lush green plants add a natural touch beside a small black table. Light pours in from large windows adorned with light curtains, creating a tranquil atmosphere.

5 out of 5 average rating, 5 reviews

Luxury Bungalow w. Scenic Views | The Nook

A bright and airy solarium features a dining area with a circular table and several brightly colored chairs. Natural light floods the space through multiple windows adorned with sheer curtains. Additional seating is available with a wicker chair and a sideboard is positioned nearby.

Place to stay in Marlboro Township

4.83 out of 5 average rating, 18 reviews

Solarium/Art studio

5 out of 5 average rating, 14 reviews

A charming exterior of a spacious home is showcased, featuring a combination of textured stone and painted wood siding. Colorful autumn foliage surrounds the property, providing a vibrant contrast. Sunlight filters through the trees, creating a warm and inviting atmosphere.

Farm stay in Philipstown

Country Estate on Maple Syrup Farm, Tesla Charging

A spacious bedroom is seen featuring a comfortable bed with a patterned coverlet. Two bedside lamps provide soft lighting, complementing the natural light coming through a large window. A small bedside table holds books, enhancing the inviting atmosphere of the room.

4.94 out of 5 average rating, 112 reviews

Hikers retreat in the Hudson Valley