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...
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...
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.
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...
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...
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...
Joseph Lorino Dual Lic.
(212) 452-4513
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.
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!
Taintor Way
$20,000
Millbrook, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 821229
SUMMER Rental – Available August & September 2025 at $20,000 per month. This historic 1920 converted barn exudes charm and is the perfect location for a country getaway close to the Village of Millbrook. Once featured in Elle Decor Magazine, the home is tastefully furnished with primitive antique furniture and folk and modern art. A great room with soaring ceilings and fireplace, chef’s kitchen with access to the terrace, a hall bath, and primary suite with an office are on the main level. Upstairs are two additional bedrooms and a bath. Enjoy the summer sun by the heated, 10’ x 15’ gunite pool, outdoor shower, fishing for trout and bass in the stocked pond, barbequing on the terrace or under the stars in the hot tub. Amenities include air conditioning and wifi. This rental is located less than a mile from the Village of Millbrook’s quaint shops and superb restaurants....
Mt Merino Road
$20,000
Hudson, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 824341
Stunning Hudson River Property ! Available for Summer 2025 June July August. Newly and stylishly renovated with gorgeous light in all the right places. The property gently slopes down to the Hudson River...open views to the endless changing natural landscape. An open floor plan flows with ease and privacy, a large deck off the kitchen and living room to enjoy al fresco dining and entertaining. The panoramic water and country scape is discreetly fenced over 2 of its acres for your furry friends.The pool is nothing short of spectacular, wisteria flowers drape over a pergola and seating area, quite the spot to relax and enjoy the quiet and calm breeze. A separate barn/studio with bed and bathroom offer additional guest accommodation or office space. You won't want to leave...but if you do - it is 2 miles (5 min drive) from the town of Hudson with amazing restaurants, shops, farmers...
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....
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...
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,...
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...
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.
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!
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