Vacation rentals in Philipstown

4.93 out of 5 average rating, 131 reviews

Home in Philipstown

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.

4.9 out of 5 average rating, 230 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.

4.94 out of 5 average rating, 254 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, 414 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.

4.94 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.

4.99 out of 5 average rating, 145 reviews

A welcoming porch features two wooden chairs with soft cushions, separated by a small table. Railings and columns frame the space, while soft shadows are cast by the afternoon sun. A glimpse of the quiet street and surrounding greenery can be seen in the background.

Apartment in Beacon

1 Bedroom with Backyard & Front Porch, Central Air

In heart of Beacon. Large and sunny, on a very quiet block. Private with its own entrance. Back-yard, central air, wifi, TV. Walkable to hiking and Main Street. Queen-sized bed. BEFORE YOU BOOK - 200 year old house - hosts live upstairs and there is another guest apartment. You WILL NOTICE sounds from others. QUIET HOURS from 10 PM to 8 AM. As a courtesy to others, please keep conversations quiet after 10 PM. We only book guests with favorable Airbnb reviews. NO SMOKING please.

4.86 out of 5 average rating, 187 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!

4.94 out of 5 average rating, 128 reviews

A charming red cabin is nestled among vibrant autumn foliage, surrounded by tall trees. The cabin features multiple windows, allowing natural light to illuminate its interior. A stone wall lines the front, and a set of wooden steps leads to the entrance.

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

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, 163 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, 110 reviews

The bathroom features a tiled shower enclosed by a floral shower curtain, providing privacy. A vanity sink with modern fixtures is visible, along with a wall-mounted mirror and a towel rack. Natural light enters from a nearby window, enhancing the space.

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, 284 reviews

A green yard encompasses a vegetable garden enclosed by a rustic fence, rich with plants and flowers. Solar panels can be seen in the background, with lush trees providing shade around the area. A chicken wanders freely, contributing to the serene outdoor atmosphere.

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.

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Popular amenities for Philipstown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Philipstown

4.92 out of 5 average rating, 204 reviews

A charming early century Cape is seen in the background, surrounded by lush greenery and a wooden fence. Two horses graze peacefully on a grassy area in the foreground, with a clear blue sky above and trees lining the property.

Home in Philipstown

The Garrison Cottage

4.94 out of 5 average rating, 54 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

4.96 out of 5 average rating, 67 reviews

The kitchen area features white brick walls, providing a clean and modern backdrop. A stainless steel microwave and coffee maker are prominently displayed alongside wooden cutting boards. A shelf above holds clear jars, creating a functional and aesthetic appeal.

Apartment in Newburgh

Quaint Newburgh Retreat

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

5 out of 5 average rating, 14 reviews

An aerial view of a spacious home with French country architecture is surrounded by lush greenery. A large driveway leads to the entrance, which features a stone pathway and landscaped areas with rocks and plants. The natural setting enhances the home's private atmosphere.

Farm stay in Philipstown

Country Estate on Maple Syrup Farm, Tesla Charging

4.94 out of 5 average rating, 111 reviews

A winding gravel pathway is bordered by a vibrant display of wildflowers and greenery. A charming fence leans gently against a stone wall, enhancing the natural beauty of the garden. Sunlight filters through the foliage, illuminating the colorful blooms.

Home in Philipstown

Hikers retreat in the Hudson Valley

4.79 out of 5 average rating, 226 reviews

Cottage in Cold Spring

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard