500+ Hudson Valley Rentals

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125 Copper Ridge Trail
$45,000

Windham, NY
Rental
Rooms: 30
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!...

(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...

88 Friar Tuck Road
$25,000

Ancramdale, NY
Rental
Rooms: 11
Bedrooms: 5
Bathrooms: 4
Web ID: 6288654

Spend your summer in the country enjoying this privately located home in the Ancram area which is convenient to The Berkshires and other surrounding areas that offer hiking, boating and cycling. Visit the local farmer's markets and dine out in the area's many fine restaurants. This 1880's Victorian features 5+ bedrooms, 3.5 baths, large chef's kitchen with a dining area. There is a cozy family room which opens to a screened in porch and patio overlooking an expansive lawn and heated in ground pool. Plenty of room to entertain family and friends. Located on 21+ acres at the end of a country lane. Would consider 1 month for summer rent Longer term considered. Convenient to Mashomack Club and area private schools.

(203) 253-1800

200 Chase Road
$25,000

Pine Plains, NY
Rental
Rooms: 15
Bedrooms: 7
Bathrooms: 8.5
Web ID: 6308706

FALL RENTAL $25,000 per month. Overlooking 119+ acres of rolling hills this property offers an ideal setting for the perfect country lifestyle. The spacious country house with seven en-suite bedrooms and has been fully customized with generously sized rooms, crown moldings and beautiful flooring throughout. Outdoor features include a large bluestone terrace, heated gunite pool, outdoor fireplace, dining loggia and outdoor kitchen. There are 3 barns, 3 ponds, and a 2-acre fenced orchard on the property. There is a horse barn & 8 paddocks. Just a 10 minute drive to Mashomack. Available now.

(203) 253-1800

215 Mill Road
$20,000

Rhinebeck, NY
Rental
Rooms: 14
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

6 Apple Summit Lane
$14,000

Lagrangeville, NY
Rental
Rooms: 15
Bedrooms: 5
Bathrooms: 3
Web ID: 6317619

Short-term/flexible rental available in beautiful Lagrangeville, New York. Fully furnished and equipped with all the amenities you could dream of. Spread out and enjoy the beauty of this 5 bedroom/3 bathroom home on almost 6 acres complete with heated pool and private garden. The main level boasts hardwood floors, crown molding & decorative wainscoting. EIK w/ granite countertops, center island w/ oven, SS appliances, pantry & is open to the Family Room which features a stone-faced wood burning fireplace. The formal dining room is open to the living room and is the perfect space for gatherings. Full bath, mudroom/laundry room, office & back staircase complete the main living area. Upstairs boasts 5 bedrooms, sitting room, main bed w/ensuite bath & WIC, full bath & game room. Located on park-like property with mature trees and abundant flowering perennial gardens. This pristine home is located in a picturesque subdivision, minutes to Taconic...

(203) 253-1800

State Route 82
$13,000

Ancram, NY
Rental
Rooms: 8
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

8 Dutchess Cove
$11,000

Holmes, NY
Rental
Rooms: 10
Bedrooms: 3
Bathrooms: 3
Web ID: 6322911

Vacation year round with swimming, skating, kayaking and a private beach. This contemporary home is perfectly situated on a peninsula in beautiful Lake Dutchess guaranteeing lake views from every room in the house. The modern architecture, attention to detail and well thought out floor plan truly make this a one-of-a-kind home. The .45 acres offer privacy from neighbors when entertaining on one of many decks or enjoying conversation around a night-time fire pit. This home was tastefully renovated in 2021 with every modern amenity for an energy efficient home. As you enter the great room, your eye is drawn to the wall of glass overlooking the lake. The glass walls are highest rated Origin glass and were built to reflect the heat in the summer and absorb the heat in the winter. They are storm proof and 0.28 U factor. There is radiant heating throughout the entire house, which minimizes...

(203) 253-1800

481 Old Albany Post Road
$10,000

Garrison, NY
Rental
Rooms: 12
Bedrooms: 3
Bathrooms: 4
Web ID: 6323285

Escape the city and indulge in the charm of this 2,500-square-foot luxury home rental nestled on a private 28.3-acre estate in Garrison, NY. This mid-century gem boasts 4 bedrooms and 3.5 baths, offering the perfect blend of modern amenities and cozy character. Unwind by the stone fireplace in the cozy library, or host gatherings in the large entertaining kitchen with sliding walls of glass that open to a screened-in porch. Savor homemade pizza from pizza oven, or take a dip in the private pool with a serene waterfall feature. Explore the parklike woods, hardscaped from onsite rocks to be in harmony with the natural surroundings. Complete with a pond and a charming poolside tea house, for a true taste of country living, just 53 miles from the bustle of NYC. Whether you're seeking a weekend getaway or a year-round retreat, this private oasis promises an unforgettable experience.

(203) 253-1800

340 Northern Boulevard
$10,000

Germantown, NY
Rental
Rooms: 12
Bedrooms: 4
Bathrooms: 4
Web ID: 6326765

Experience the historic charm of The Peary Homestead, a Hudson Valley icon, featured in Veranda and Homes & Gardens. Originally built in 1823 by sea captain Robert Peary and renovated in 2020 by architect Chip Bohl & designer Louise Copeland. The home seamlessly blends Hudson Valley contemporary style with traditional art & antiques. The exterior showcases English-style country gardens, a greenhouse, an inground pool, and lotus water gardens. Inside, you'll find 4 bedrooms/3.5 baths. The main level includes an expansive chef's kitchen, formal dining room, living room, office, half bath, sunroom, and a cozy screened porch. The upper level features a primary bedroom with a gas fireplace, en-suite bath, and dual walk-in closets, plus 2 additional bedrooms, a full bath, and a guest suite with bath. A separate 2 bedroom, full bath guest house above the garage provides extra space for guests. Minutes from Hudson & Rhinebeck, enjoy all the...

(203) 253-1800

159 Pitcher Lane Lane
$10,000

Red Hook, NY
Rental
Rooms: 8
Bedrooms: 3
Bathrooms: 3
Web ID: 6326894

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

478 Tower Hill Road
$9,000

Millbrook, NY
Rental
Rooms: 14
Bedrooms: 4
Bathrooms: 4
Web ID: 6328348

Escape to this enchanting four-bedroom, four-bathroom home in the heart of Millbrook, New York. Perfect for year-round living, this charming farmhouse offers breathtaking views of the surrounding countryside. Cozy up by one of the four fireplaces on cool evenings, or take a dip in the private pool during the warmer months. With its prime location, you'll enjoy easy access to Millbrook's quaint shops, dining, and nature trails, while relishing the peace and privacy of this serene retreat. Each bedroom is spacious and comfortable, providing a perfect blend of elegance and warmth. This home is filled with character and charm, offering an inviting atmosphere for relaxation or entertaining. Whether you're sipping your morning coffee while gazing out at the scenic landscape or enjoying a firelit evening with friends, this rental is a true gem.

(203) 253-1800

692 Budds Corners Road
$8,500

Red Hook, NY
Rental
Rooms: 8
Bedrooms: 4
Bathrooms: 3
Web ID: 6317662

Welcome to Horizon Hill- Step back in time and embrace the timeless charm of Horizon Hill, a stunning 1837 farmhouse located in the picturesque town of Red Hook, New York. This enchanting four-bedroom, two and a half bath home offers a unique blend of historic elegance and modern amenities, making it the perfect retreat for those seeking tranquility and comfort. Four generously sized bedrooms provide ample space for family and guests, ensuring comfort and privacy for all. The living room features a cozy fireplace, perfect for chilly evenings and creating a warm, welcoming atmosphere. Enjoy the great outdoors with private hiking trails and a serene swimming pond, perfect for relaxation and recreation. Just minutes away from Bard College and the charming villages of Tivoli and Rhinebeck, Horizon Hill offers easy access to local shops, dining, and cultural attractions.

(203) 253-1800

15 Kirby Hill Road
$8,000

Pawling, NY
Rental
Rooms: 9
Bedrooms: 4
Bathrooms: 4
Web ID: 6329150

Now for rent is one of Quaker Hill's most prestigious estate homes. The main estate at Kirby Hill Farm is available as a year-round, impeccably furnished and equipped residential rental. Set on close to 250 acres and one of the region's finest equestrian facilities. The circa 1860 colonial farmhouse boasts 3,942 square feet. There are two separate parlor rooms on the first floor, along with a formal dining room, a well-appointed kitchen, additional dining area, convenient first floor laundry room and two powder rooms, with one that can be accessed from the patio and pool area. Above is the primary suite with multiple walk-in closets, sitting room, office area and full bath, two additional bedrooms and full bath. Be sure not to miss the third floor that is currently set up as a sleeping loft with full bath. Outdoor amenities include an inground pool, tennis court, patio area, fire...

(203) 253-1800

155 Horton Road
$7,750

Cold Spring, NY
Rental
Rooms: 13
Bedrooms: 4
Bathrooms: 3
Web ID: 6335682

Welcome to 155 Horton Road, a beautifully restored 1900s colonial homestead that perfectly blends historic charm with modern luxury. Nestled on the outskirts of Cold Spring, this unique rental offers both tranquility and convenience, set on a private 20-acre wooded lot with exclusive access to a private lake featuring its own island. The home boasts a newly renovated kitchen with stainless steel appliances, elegant stone countertops, and plenty of cabinet space, while the open dining room provides an inviting space for family gatherings. The spacious living room, complete with a cozy fireplace, is ideal for both relaxation and entertaining. The primary suite is a true retreat, featuring a walk-in closet, a private sitting room, and a luxurious en-suite bath. The home also includes three additional bedrooms and two updated full baths. With ample storage, including walk-in closets and attic space, you'll have all the room you need. The private driveway,...

(203) 253-1800

57 Coldwater Street
$7,500

Hillsdale, NY
Rental
Rooms: 16
Bedrooms: 4
Bathrooms: 3
Web ID: 6335949

This beautiful home is available for a 12 month term. At the crossroads of the Hudson Valley's most visited towns lies the charming Hamlet of Hillsdale. The quaint neighborhood's architectural star-of-the-show is this fully restored Masonic Temple which simultaneously offers warmth and functionality. Zoned for both residential and commercial opportunities the Temple can easily be your cozy upstate dream home, the space to grow your personal business and most ideally: Both. Rarely is a space of such beauty and square footage offered to the market in pristine condition. Boasting impressive 14ft tin ceilings throughout and an abundance of large steel casement windows, the expansive space is illuminated with natural light throughout the entire day. Two bedrooms, 3 Bathrooms and a streamlined kitchen create a move-in ready residence. Views of the surrounding hills from this gated, hedged and private property make you feel worlds away while still having the ease and...

(203) 253-1800
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