88 Hudson Valley Rentals

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150 Trailside Road Rd
$70,000

Windham, NY
Rental
Bedrooms: 8
Bathrooms: 6
Web ID: 155010

Experience the ultimate in mountain luxury at this stunning home that is perfectly nestled along the slope at Windham. This spectacular property offers everything you need for your extended stay. Experience what each season in the Catskills has to offer in the comfort of this sprawling retreat offering nearly 6,900 square feet of living space, including eight bedrooms and six full bathrooms. (7BRM/& Bath but the owner's ensuite will be closed off and not used as part of the rental) Some of the key features of this property include panoramic views and a prime location with access to the slopes, lodge and restaurant just outside your front door. The great room boasts a soaring ceiling that is 20' high, wall of glass and one of four wood-burning fireplaces. The state-of-the-art kitchen is equipped with a Viking stove, microwave, and dual dishwashers, ideal for creating the perfect meal. There is a...

(203) 253-1800

292 South Street
$65,000

Windham, NY
Rental
Rooms: 8
Bedrooms: 5
Bathrooms: 6
Web ID: 154337

Your 2024-2025 Windham Vacation Rental awaits! Nestled at the edge of Windham Mountain Club's North Lot, this stunning property offers unparalleled convenience and luxury for large groups and ski enthusiasts alike. Here's why this property is perfect vacation rental for the upcoming 2024-2025 ski season:Key Features & Amenities*Sleeps 12 comfortably with 1 king bed, 3 queen beds, and 2 sets of bunk beds*Five Spacious Bedrooms including four ensuites, ensuring privacy and comfort for everyone*Third-Floor Master Suite featuring a private 620 sq. ft. rooftop terrace with breathtaking views*Chef's Kitchen boasting high-end LG appliances and sleek quartz countertops*Great Room with soaring 10' ceilings, walls of glass framing stunning ski slope views, and a cozy fireplace*Two Laundry Rooms and a ski/boot room for added convenience*Ample Parking with 4 spaces per unit1 in a heated garage and 3 in front of the building*High-Speed Wired Broadband (Cable, DSL, Fiber Optic) for all your connectivity...

(203) 253-1800

1 Bog Hollow Road
$38,500

WASSAIC, NY
Rental
Rooms: 20
Bedrooms: 6
Bathrooms: 8
Web ID: 22730860

Academic rental. Inquire for summer pricing. Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389 acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two hours from New York City, access is via a private gated road that winds through trees, past old stonewalls with glimpses of open meadow and a serene pond. Spacious rooms perfect for entertaining include a large great room with a soaring peaked ceiling and a 20' stone fireplace, a sun-filled formal dining room with three exposures and a huge chef's kitchen with a massive stone fireplace and adjoining catering kitchen, a marble paneled powder room and mud room. Beautiful reclaimed chestnut...

153 Two Town Road
$27,500

Craryville, NY
Rental
Rooms: 8
Bedrooms: 3
Bathrooms: 2
Web ID: 155316

Luxury Barn Retreat for RentEscape to the countryside in this stunning luxury barn nestled on private grounds. Enjoy sunny days and breathtaking views of expansive fields and a tranquil stream.This spacious home offers three bedrooms and two modern bathrooms. The gourmet kitchen is fully equipped, and the inviting living areas feature a cozy wood stove and a fireplace.Step outside to your private oasis, complete with a fire pit, barbecue area and distant mountain views. Additional amenities include a foosball table and a dedicated card table, gym, sauna and hot tub.Rent this exceptional property and experience the perfect blend of luxury and leisure!

(203) 253-1800

64 Klein Avenue
$20,000

Hunter, NY
Rental
Rooms: 9
Bedrooms: 2
Bathrooms: 3
Web ID: 155140

Experience the pinnacle of ski-in/ski-out luxury at Vail Resort @ Hunter Mountain. This condo offers the ultimate convenience of direct slope access from your door. Enjoy the winter season skiing on fresh snow, with the privilege of being among the first on the lifts and forget the hassle of parking with your reserved spot. The spacious great room welcomes any family returning from the slopes to unwind by the fireplace while dinner cooks. Retire to the primary suite with jet tub and cozy fireplace, additional bed and bath with ski slope views, just bring your ski equipment as this unit is turnkey. This exclusive lodge living, complete with easy elevator access to the Copper Tree Restaurant and Hunter Mountain's main ski lodge, is a rare find. Leave your car parked all weekend; your winter retreat awaits at 507 Pinnacle.

(203) 253-1800

274 Route 65
$18,000

Windham, NY
Rental
Rooms: 7
Bedrooms: 4
Bathrooms: 4
Web ID: 154820

This fully equipped seasonal rental boasts four bedrooms, including two en-suites, three full bathrooms, one half bathroom, a fireplace, washer/dryer, ski room, off-street parking, and a shuttle service from the development to Windham Ski Resort (WMC). Enter into a welcoming ski room leading to an open layout ideal for relaxation or socializing with friends and loved ones after a day on the slopes. It includes a convenient half bath with laundry facilities and a fully equipped kitchen with a breakfast bar that seats six. The living room features a cozy stone wood-burning fireplace and sliding doors opening to a patio. The second level has two en-suite bedrooms, and the third floor offers two additional bedrooms and a full bathroom, providing plenty of space and privacy for everyone. Generous closet space ensures ample storage. The property is part of a development that offers a shuttle bus service for convenient access to...

(203) 253-1800

71 Hunter Drive
$14,000

Hunter, NY
Rental
Rooms: 10
Bedrooms: 3
Bathrooms: 2
Web ID: 155267

Seasonal rental without the stress: NO snowplowing, NO worries about propane /oil heating, NO trips to dispose garbage...just relax and enjoy yourself by the wood burning fireplace. Hurryup before the 2024-2025 Ski Season starts in Hunter-Vail resort !Perfectly located condominium in Hunter Highlands Complex, just 3 minutes from the ski slopes. Just renovated, and tastefully furnished, fully equipped, easy accommodating 6 tenants. Everything is new: beds, mattresses, bedding, bathrooms, flooring, washer and dryer....clean, cozy and inviting. Responsible tenants only!

(203) 253-1800

754 Merwin St
$12,000

Jewett, NY
Rental
Rooms: 7
Bedrooms: 3
Bathrooms: 2
Web ID: 155336

Seasonal Winter Rental available monthly or from 12/1/24 - 4/ 7/25This well cared for 3 Bedroom, 2 bath log home incorporates all the elements for comfortable, relaxing living! The living room has sky lights and wood burning stove that provides comfort and warmth in the winter time, Minutes to Hunter Ski Mountain & Windham. Don't miss out on all the winter time fun!Available for winter Seasonal Rental!

(203) 253-1800

46 Mitchell Hollow Rd Rd
$12,000

Windham, NY
Rental
Rooms: 11
Bedrooms: 5
Bathrooms: 3
Web ID: 155337

Seasonal rental available for ski season starting 12/21/24 - 4/8/25 or monthly..Great location to Town & Windham Mountain ClubHas view of Windham Mt. from the deckThe rooms are spacious and well kept. The downstairs has 2nd kitchen area.

(203) 253-1800

286 Blue Hill Rd Rd
$12,000

Hudson, NY
Rental
Rooms: 14
Bedrooms: 5
Bathrooms: 4
Web ID: 154240

Find your sanctuary at 286 Blue Hill Road, a captivating, fully furnished, seasonal rental nestled on over 10 acres of secluded land. This exceptional upstate Colonial retreat, featured in Vogue Living AU and New York Magazine, offers a serene English countryside-style experience perfect for those seeking tranquility and rejuvenation in the Hudson Valley. Impeccably renovated, this expansive home blends timeless elegance with modern comfort. Step into a world of bespoke luxury, highlighted by a hand-made Dutch barn door, contemporary lighting fixtures, and a stunning glass NanaWall that opens to a spacious back deck, overlooking a lush backyard with Catskill Mountain views peeking through the wooded trails. The beautiful hardwood floors and exposed wood beams throughout enhance the inviting atmosphere of this exquisite residence. The large chef's kitchen is a true masterpiece, featuring custom enclosed cabinets with open shelving, a cream-colored concrete countertop, 8 burner gas cooking range stove, Garden window...

(203) 253-1800

State Route 82
$11,000

Ancram, NY
Rental
Rooms: 8
Bedrooms: 3
Bathrooms: 3
Web ID: 155114

The 1850 Greek Revival home in Ancram, NY, is a testament to classic architecture and modern care. This well-maintained property offers a private setting with a screened barn that provides serene pond views, all nestled on a generous 7-acre lot. The residence boasts three bedrooms and two and a half baths, featuring wood floors that add warmth to the space. The formal living room, spacious kitchen with top notch appliances, and dining area create an inviting atmosphere for both relaxation and entertainment. A convenient mud room with laundry facilities, a cozy den, and an upper floor with a primary ensuite enhance the living experience. Additional amenities include a guest house and a three-car garage, ensuring ample space for visitors and vehicles. The location is ideal for outdoor enthusiasts, being close to Catamount for skiing and within a comfortable distance from the cultural and educational contributions of Hudson, Hillsdale, and nearby...

(203) 253-1800

7817 Main Street St
$10,000

Hunter, NY
Rental
Rooms: 9
Bedrooms: 5
Bathrooms: 2
Web ID: 154944

Looking for a winter retreat? This cozy 5-bedroom, 2-bathroom house at the base of Hunter Mountain is just the place. It's perfect for the season, sitting next to a peaceful stream with a big yardplenty of space for snowball fights, snowmen, or just hanging out with family and friends after a day on the slopes.Inside, there's room to spread out with a relaxed, homey feel throughout. The five bedrooms are comfy, so everyone has a place to unwind. And yes, dogs are welcome!At $10k for the season (December 1st to April 1st), it's a great and affordable way to enjoy the Catskills in winter. Your perfect mountain escape is waiting!

(203) 253-1800

4 Albert Court
$10,000

Hensonville, NY
Rental
Rooms: 5
Bedrooms: 1
Bathrooms: 2
Web ID: 155059

This spacious 1-bedroom, 2-bathroom apartment is perfect for your 2024-2025 winter season getaway. Located just minutes from Windham Mountain, it features a large deck with stunning mountain views, ideal for aprs-ski relaxation. Pets are negotiable. Don't miss out on this prime location for winter fun!

(203) 253-1800

292 Van Etten Rd Rd
$10,000

Windham, NY
Rental
Rooms: 9
Bedrooms: 3
Bathrooms: 3
Web ID: 152375

The Seasonal Winter Rental rate is $45,000. This is a ncely appointed home with open floor plan, wood burning fireplace, large deck with fantastic views.The fully stocked gourmet kitchen is a chef's delight. House is situated on 5.5 Acres with outdoor fire pit & adirondeck chairs. Also the yard has a slight grade which is excellent for sleigh riding. Close to State land and 15 minutes to Windham Mountain Ski Club or Hunter Mountain. Also, inquire about Summer rental. Rental rate to be determined according to length of time rented.

(203) 253-1800

159 Pitcher Lane
$9,500

Red Hook, NY
Rental
Rooms: 8
Bedrooms: 3
Bathrooms: 3
Web ID: 154403

Pre-dating the American Revolution by more than 30 years, this expertly restored circa 1747 Dutch vernacular furnished farmhouse is gracefully sited on a quiet country lane. The historic William Pitcher farmstead boasts 3,100 square feet of living space- three bedrooms, two and a half bathrooms, a gracious nine-foot wide center hall, two parlors with wood-burning fireplaces, a mud room, and a spacious eat-in kitchen with pastoral views to the north. A large bluestone patio off the kitchen is shaded by a grove of ancient locust trees. With original wide board floors, lime-washed plaster walls, and massive exposed beams, as well as brand new appliances and high-efficiency systems, this home has 18th century charm with 21st century comforts.Convenient to celebrated farm markets, scenic walking trails, restaurants, and cultural venues. Fifteen minutes to the Taconic Parkway or Rhinecliff train station.

(203) 253-1800

52 Longview Drive
$9,000

Chatham, NY
Rental
Rooms: 14
Bedrooms: 3
Bathrooms: 3
Web ID: 154195

It's not too late to plan that perfect winter vacation to the Hudson Valley and idyllic Chatham, New York. There's talk of a great ski season so choose between Catamount or Jiminy Peak - just a stone's throw away or head over to Hunter Mountain. Either way, you'll get some great skiing in. But after you've skied to your heart's delight, visit museums and farmers markets, antiquing or dining out, eastward toward the Berkshires or back to Hudson, NY. Then unwind and relax in the sauna, hot tub, or by a crackling, warm fire. Lots of room to unwind, cook gourmet meals, enjoy privacy and take in the views. Great for family gatherings or working remotely. Peace of mind with a whole house generator at the ready.Are you ready to book your stay!!

(203) 253-1800
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