Holiday rentals in Graymoor

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Top-rated holiday rentals in Graymoor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.

Home in Highland Falls

Modern 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

LocationValueAccuracy

4.99 out of 5 average rating, 116 reviews

Guest favourite

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.

Flat 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.

FamilyLocationBreakfast

4.9 out of 5 average rating, 278 reviews

Top guest favourite

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

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

ValueLocationPets

4.99 out of 5 average rating, 191 reviews

Guest favourite

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

ValueFamilyCheckout

4.94 out of 5 average rating, 144 reviews

Top guest favourite

A charming home nestled among trees features a spacious front porch adorned with planter boxes. Lush greenery and colorful flower beds surround the property, and a large boulder adds a natural element to the landscape.

Home in Cold Spring

Home in Cold Spring- Farm Stay!

Escape to our charming home nestled on five acres of farmland. This stay offers both seclusion and convenience, providing an ideal retreat for families, friends, or anyone seeking a peaceful countryside experience. Outdoor Space: -Walkable property featuring goats, chickens, horses, and donkeys -Large front porch featuring stunning mountain views and sunsets -Nearby hiking trails Location: -Five-minute drive to the quaint village of Cold Spring -Many shops, restaurants, and river views

LocationFamilyShared spaces

4.99 out of 5 average rating, 104 reviews

Superhost

A spacious living area features exposed wooden beams and a neutral-toned couch positioned over a patterned area rug. An elegant dining space is visible through an archway, with a chandelier hanging above a wooden table. Natural light filters in through nearby windows.

Home in Philipstown

Crystal Cottage Retreat

Treat yourself to a getaway in the charming Hudson Valley! This 2-bedroom, 1.5-bath Garrison vacation rental was originally constructed in 1929 and recently renovated to include an array of modern amenities and comforts. Crystal Cottage boasts a private, cozy atmosphere on 1 acre of land complete with an interior fireplace, sunroom, spacious patio, and charcoal grill! You’ll be within minutes of stunning valley hikes and only a 1.5-hour train ride away from New York City

FamilyLocationHospitality

4.85 out of 5 average rating, 73 reviews

Guest favourite

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

LocationFamilyLayout

4.95 out of 5 average rating, 137 reviews

Top guest favourite

The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.

Home in Highland Falls

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

LocationFamilyDecor

5.0 out of 5 average rating, 106 reviews

Guest favourite

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

LocationFamilyCheckout

4.96 out of 5 average rating, 252 reviews

Guest favourite

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!

ValueLocationHiking

4.83 out of 5 average rating, 110 reviews

Guest favourite

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 with your pet, and explore four acres of Hudson Valley landscape shared with the main house next door.

FamilyLocationWifi

4.97 out of 5 average rating, 229 reviews

Guest favourite

An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.

Guest house 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

ValueLocationLaundry

4.93 out of 5 average rating, 335 reviews