500+ 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

Stanford Road
$50,000

Millbrook, NY
Rental
Bedrooms: 4
Bathrooms: 5.5
Web ID: 817488

Available Memorial Day to Labor Day 2025 at $50,000 per month. Enjoy the summer in this beautifully appointed farmhouse just a few minutes from the village of Millbrook. The 4,500+ square foot main house, c. 1880, was completely renovated in 2010, finished at a high standard and includes four en suite bedrooms and two half baths. The interior design is clean and minimal. Outdoor amenities include a covered porch, open patio and a pergola topped patio with fireplace providing endless opportunities for entertaining or relaxing. Nearby is a 3,300+ square foot guest/pool house that offers expansive living and entertaining space with one bedroom and two baths plus a heated gunite swimming pool. Beautiful perennial plantings, extensive lawns, trails throughout the property and two ponds on 43+ acres enhance the rural feeling of this wonderful property.

(203) 253-1800

Byrds Hill Road
$45,000

Pawling, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 821227

Stunning Summer Rental with Pool near Scenic Quaker Hill in Pawling! Available this Summer (July 1st to September 1st), this beautifully renovated Antique Colonial is the ideal summer retreat. The home boasts a spacious kitchen featuring a center island, an open dining and living area complete with a cozy fireplace, and a separate den for relaxation. On the main floor, you'll find a luxurious primary suite that includes a lovely private bath equipped with both a shower and a separate soaking tub. Upstairs, three additional bedrooms share a full bath, providing ample space for family or guests. Step outside to enjoy your own private oasis, featuring a heated gunite pool and spa, a basketball hoop for some fun, and a charming patio with a fire pit—perfect for evening gatherings. Conveniently located under two hours from NYC and just minutes from Metro-North, this summer rental offers everything you need for the perfect...

(203) 253-1800

Schoolhouse Road
$40,000

Staatsburg, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 813638

SUMMER RENTAL – Available July through Labor Day at $40,000 per month. Quintessential c.1765 country estate in a peaceful and private setting. Escape to the countryside and spend the summer lounging by the heated gunite pool, dining al fresco on the bluestone patio, roasting marshmallows around the firepit, exploring the numerous trails throughout the 154 acres and fishing in the pond. This expansive 6,743 square foot main house offers five/six bedrooms and six baths. The home is beautifully furnished and has a timeless charm with the numerous fireplaces, wide board floors, beamed ceilings and built-in bookcases. There is a top of the line kitchen with sunroom, family room, den with fireplace, library, formal dining room and office. Adding to the list of amenities is a screened porch overlooking the stream and pond, movie theater, ping pong room, mudroom with dog wash and gym. The two-car garage includes an electric car...

(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...

Old Conklin Hill Road
$30,000

Stanfordville, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 6324496

SUMMER RENTAL - Available July 1, 2025 - August 31, 2025 for $30,000 per month. Exquisite 1790's country house completely restored and beautifully furnished. There are period moldings, five fireplaces, five bedrooms, four baths, and a generator. Also, a 20' x 50' gunite salt water pool with pool house fully equipped with full kitchen and bath. There is a separate building near the pool with a ping pong table. The gardens are lovely with a stone terrace behind the house and near the pool. The perfect seasonal rental, close to Mashomack. Also available as a yearly rental for $12,000 per month. Owner would consider a short term Spring rental.

(203) 253-1800

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

Mill Road
$20,000

Rhinebeck, NY
Rental
Bedrooms: 6
Bathrooms: 7
Web ID: 6335464

Welcome to The Waterfall House: One of the most unique architectural masterpieces in the area designed by the late Steve Mensch. This compound includes a main house with fully retractable glass walls, 3 bedrooms, 4 bathrooms, a fireplace, and a media room. The main house layout is flipped with the primey bedroom below the main living space, two sleeping areas below the primary, and a media room on the lower level. The guest houses are connected by stone and elevated pathways providing a rare and romantic approach. Guest house 1 has a sleeping nook, full bathroom and covered porch overlooking the quiet river upstream. The second guest house has a kitchen, 2 bedrooms and water views. Finally, there is a 3 story studio building which was once used as the owners architecture and painting studio. The studio has a direct view of the waterfall and incredible architectural proportions....

(203) 253-1800

90 Mill Road
$20,000

Northeast, NY
Rental
Rooms: 9
Bedrooms: 5
Bathrooms: 4
Web ID: 156168

Welcome to a timeless piece of history, the Ezra Clark House, believed to be the oldest home in the village of Millerton. Built in 1780, this remarkable estate stands as a testament to centuries of architectural craftsmanship and refined elegance.Step into the main house, where 2,625 square feet of living space awaits. With 3 bedrooms, 2.5 bathrooms, and two inviting living areas, this home effortlessly combines historic charm with modern comfort. Whether you're unwinding by the fireplace or entertaining guests on the spacious outdoor patio or by the gunite pool, this property offers the most discerning renters with a little bit of everything.Need a quiet space to work or study? The private office provides the perfect retreat. Step outside onto the beautiful brick patio or second-floor balcony, where you can savor tranquil moments overlooking your own private pond.But the magic doesn't end there. Adjacent to the main house, discover a...

(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

5 Fulton Homestead Rd
$17,000

Milan, NY
Rental
Rooms: 10
Bedrooms: 5
Bathrooms: 3
Web ID: 155770

Nestled on 85 private acres in northern Dutchess County, Fulton Homestead offers a rare opportunity to experience the best of country living in a beautifully renovated 1830s farmhouse. Fully furnished and available for long-term or seasonal rental, this historic property is a truly unique offering for those seeking privacy, comfort, and charm in the heart of the Hudson Valley.The home features 5 bedrooms, 2.5 bathrooms, a dedicated office, and two gracious Greek Revival parlors with 10-foot ceilings, making it ideal for year-round living or a seasonal retreat. The newly updated kitchen, designed with both style and function in mind, is perfect for entertaining, while four working fireplaces and original artwork throughout add warmth and character.Outside, the serene surroundings invite exploration of rolling farmland, wooded trails, and open fields, or relaxation by the lovely swimming pool, available in season. The beautifully landscaped grounds create a tranquil setting for recreation and leisure,...

(203) 253-1800

Hill 99
$16,500

Woodstock, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 831283

Secluded Mountain Chalet with Breathtaking Views and Poolside Lodge - Set atop nine private acres, this stunning mountaintop chalet offers a rare combination of serenity, seclusion, and spectacular views. A long, private driveway winds through the property, leading to a retreat unlike any other. The property features a three-story main house and a separate two-story Poolside Lodge, both connected by an expansive deck with a heated pool, open from mid-May through November 1st, and a built-in outdoor grill station perfect for entertaining. Inside the main house, soaring cathedral ceilings and wide-plank wooden floors create an immediate sense of warmth and grandeur. The second floor spacious living room is anchored by a striking double-sided wood-burning fireplace, which also serves a cozy alcove office lined with picture windows—a peaceful and inspiring workspace. The adjoining kitchen is fully equipped with modern appliances, including an induction stovetop, oven, and two refrigerators. A large island with seating...

(203) 253-1800

County Route 6
$13,500

Germantown, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 6322354

Located in the heart of the Hudson Valley in Germantown, NY, Peaceful Windhorse Farm is an exceptional property that combines rustic charm with modern sustainability. Conveniently situated between the Rhinebeck and Hudson Amtrak train stations (each 20 minutes away), this 50-acre property is a nature lover's paradise. The completely pesticide free expansive grounds present diverse landscapes ideal for outdoor events or recreational activities (retreats, weddings, and film screenings), as well as agricultural purposes such as livestock cultivation or animal boarding. The 1850s four-bedroom farmhouse has been thoughtfully renovated to provide modern comforts while retaining historic charm. On the main level is a large country kitchen, a formal dining room, a cozy living room, and an office/library. There are two and a half bathrooms, two with clawfoot tubs. The farmhouse provides an inviting and charming sanctuary, making it an ideal primary residence or guest accommodation for event hosts. Across from the farmhouse...

(203) 253-1800

Douglas Lane
$12,250

Cold Spring, NY
Rental
Bedrooms: 6
Bathrooms: 7.5
Web ID: 809413

Lower Windwolde, a stately home designed and built in 1922 by Everett Meeks, the first Dean of Yale Architecture, for the only heir of Augusta Healy, the original founder of the Brooklyn Museum of Art. Home has been restored and updated over the past 10 years to its original beauty and beyond. Located on 8 private acres with a large yard and scenic 10 mile views of the Hudson River from many of the house windows, porches and swimming pool. This unique home offers 6Br/7Ba + 2/.5Ba, also includes large steam room/massage room/gym. The main floor is perfect for entertaining with an eat-in kitchen/den, butler pantry, large dining room, living room and family room/library complete with a vaulted ceiling, 7 fireplaces, a green house & a 2nd kitchen in the garage for outdoor entertaining.

(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
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