500+ Hudson Valley Rentals

Grid View Summary View

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

Copper Ridge Trail
$45,000

Windham, NY
Rental
Bedrooms: 9
Bathrooms: 7.5
Web ID: 6288635

Come enjoy the extravagant lifestyle and exquisite experience this home has to offer! From 7 fireplaces with stunning mountain views. to a fully equipped gourmet kitchen with Wolf and Sub-Zero appliances! Radiant heated floors and Wi-Fi throughout! 30 Finished rooms feature 9 Bedrooms. 7 King size beds with private suites, 4 with fireplaces and 2 with private decks. 2 Queen size beds with bathroom suite. 6 full bathrooms and 2 powder rooms. 18’ x 20’ HEATED INDOOR POOL W/ FULL BATHROOM & STEAM SHOWER. OUTDOOR HOT TUB FOR SIX. 12 SEAT STATE OF THE ART MOVIE THEATER! 2 car heated garage plus carport. One mile to Windham ski slopes and directly across for Windham Country Club and Golf Course. One mile to restaurants and shops. 10 minutes to Hunter Mountain. *This home is available for rent ask for details! By week...

(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...

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

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

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

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

State Route 82
$11,000

Ancram, NY
Rental
Bedrooms: 3
Bathrooms: 5
Web ID: 6334591

This charming 1850 Greek Revival home in Ancram, New York, generates a blend of historical elegance and modern comfort. Set in a private, serene location, the property boasts a screened barn with views of a picturesque pond, all nestled within 7 lush acres. The residence features 3 bedrooms, 2.5 baths, and beautifully maintained wood floors. The formal living room and spacious kitchen, complete with a cozy fireplace and dining area, create an inviting atmosphere for both relaxation and entertainment. Amenities include a mud room with laundry facilities, a den with another fireplace, and a primary ensuite on the upper floor. The property also has a beautiful a guest house with full bath and a three-car garage, providing ample space for visitors and vehicles. Its proximity to Catamount Ski Area, as well as the amenities of Hudson, Hillsdale, and other surrounding areas, and prestigious schools like Hotchkiss and Indian Mountain, make...

(203) 253-1800
Page:  1 2 3 4 5 6 ... 32      Next  ›