Vacation rentals in Denning Hill

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Top-rated vacation rentals in Denning Hill

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Top guest favorite
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
4.91 out of 5 average rating, 253 reviews

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.

Top guest favorite
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
4.99 out of 5 average rating, 137 reviews

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

Top guest favorite
A heated pool is surrounded by a stone deck, featuring several black lounge chairs positioned under black umbrellas. Lush greenery is visible in the background, providing a serene, natural setting.
Home in Putnam Valley
4.99 out of 5 average rating, 157 reviews

*Large Pool* Garrison Ultra Modern 5B hottub sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

Guest favorite
A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.
Cottage in Putnam Valley
4.88 out of 5 average rating, 299 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Guest favorite
Apartment in Newburgh
4.88 out of 5 average rating, 221 reviews

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!

Guest favorite
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, 148 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!

Top guest favorite
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.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 195 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.

Guest favorite
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
4.94 out of 5 average rating, 106 reviews

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.

Top guest favorite
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.
Guesthouse in Philipstown
4.99 out of 5 average rating, 117 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.

Top guest favorite
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
4.96 out of 5 average rating, 195 reviews

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

Top guest favorite
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
4.98 out of 5 average rating, 215 reviews

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.

Top guest favorite
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.
Guest suite in Putnam Valley
4.99 out of 5 average rating, 137 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.

Popular amenities for Denning Hill vacation rentals