Vacation rentals in Garrison, Philipstown

4.93 out of 5 average rating, 135 reviews

A wooden exterior house is surrounded by trees displaying autumn foliage. A pathway of stones leads to the entrance, where a deck with white railings is visible. Lush shrubs and decorative rocks enhance the natural landscaping.

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.

4.91 out of 5 average rating, 238 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.

5 out of 5 average rating, 203 reviews

A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.

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, 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

4.87 out of 5 average rating, 421 reviews

A serene Koi pond is surrounded by lush green grass and water plants. A small fountain creates gentle ripples on the surface, while orange and white Koi fish swim gracefully beneath. Natural stone tiles border the pond, enhancing the tranquil setting.

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.

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.

4.95 out of 5 average rating, 132 reviews

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.

Guest suite in Cold Spring

A serene sleeping area features a spacious bed covered with a patterned gray blanket. Nightstands are situated on either side, each equipped with lamps. Soft blue walls and a landscape painting enhance the calming ambiance. Natural light filters in through a window adorned with light drapes.

4.79 out of 5 average rating, 528 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.

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, 172 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, 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

4.9 out of 5 average rating, 461 reviews

Natural light floods a living area through large glass doors, which provide views of the garden and mountains. A comfortable couch faces a wooden coffee table, and a fireplace is situated beside a bookshelf filled with books. Decorative art enhances the space.

Chalet in Cold Spring

Mountain View Retreat

15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

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, 126 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 Garrison, Philipstown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Garrison, Philipstown

A private pool is set within a lush green lawn, surrounded by tall trees for shade. Lounge chairs line the poolside, and a large umbrella provides additional seating. The pool is framed by a clean, safety fence, creating a serene outdoor space.

4.75 out of 5 average rating, 4 reviews

Cold Spring Village Maisonette with Pool

Guest suite in Cold Spring

The family room features a comfortable seating area with a sectional sofa and armchair. A wooden coffee table sits on a patterned rug, surrounded by decorative pillows. A television is positioned on a wooden cabinet, with natural light streaming in from a small window.

4.88 out of 5 average rating, 83 reviews

Red Door Inn - One Bedroom Suite in Cold Spring.

4.94 out of 5 average rating, 85 reviews

A spacious living room features a comfortable leather couch and a large wooden coffee table. A decorative fireplace stands against a stone wall, while large windows allow natural light to illuminate the room. A nearby doorway leads to an adjacent area.

Cottage in Putnam Valley

Peaceful Cottage with Grill | Walk to Lake

A living room presents a mix of comfort and style. A gray sofa and a yellow accent chair are positioned around a central coffee table. Plants are placed in the corners, and windows with striped shades allow natural light to filter in, enhancing the cozy atmosphere.

4.88 out of 5 average rating, 33 reviews

Cottage in the village of Cold Spring

4.74 out of 5 average rating, 156 reviews

A concrete pier extends over the tranquil water, featuring two lounge chairs positioned for relaxing views of the river and surrounding landscape. Lush greenery and distant homes are visible across the water, enhancing the peaceful outdoor setting.

Home in Philipstown

Bungalow near West Point on Hudson River

A rustic cabin is nestled among lush greenery, featuring a screened-in porch with a staircase leading up to it. Stone steps are visible at the entrance, with a small garden area surrounding the base. The cabin blends with its natural surroundings.

4.89 out of 5 average rating, 46 reviews

Cabin with a View

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.

Home in Philipstown

4.92 out of 5 average rating, 204 reviews

The Garrison Cottage

An outdoor pool area is shown, featuring a rectangular pool flanked by two white lounge chairs. Surrounding greenery and tall planters add to the serene environment. The house is visible in the background, along with shaded seating options, creating a peaceful outdoor retreat.