46 houses for rent in Dutchess County

Perched to capture breathtaking, unobstructed vistas, this ultra-private 3 BDR, 3 Bath home offers a front-row seat to spectacular western sunsets rolling all the way out to the dramatic silhouette of the Catskill Mountains. Golden-hour light floods the expansive living room through a wide bank of picture windows, framing the painterly horizon and creating an unforgettable backdrop for entertaining against sweeping lawns and open fields. 2 main-level bedrooms (one en-suite) and an upper-level bedroom all drink in the surrounding green countryside, while the dining room and eat-in kitchen keep you connected to the scenery. A writer's haven surrounded by hiking trails and ponds nearby, this scenic escape is minutes from farm-to-table dining, local cultural assets like the Sharon Playhouse, The Hotchkiss Library and the Audubon Center. Easy access to local private schools (Hotchkiss, Kent, and Millbrook Schools). 2 hours via car or train to NYC. Available October 15, 2026. May 31, 2027

Annual furnished rental in a tranquil country cottage on Lake Lillinonah. This is an extremely rare opportunity to rent with direct lake frontage with a lovely grassy area by the lake and dock. This well appointed 2 bedroom home is the perfect writer's or artist's retreat, nestled on a lightly wooded hillside overlooking CT's best kept secret lake. 90 minutes to Manhattan. Enjoy the 2 patios and deck areas among the lovely perennials and stone walls with calming lake views. Relax in the quiet country life on the lake. Great for bass fishing, too

Welcome to Rollingwood! This spacious first-floor, one-bedroom condo offers comfortable living in a peaceful, well-maintained community. The inviting living area features laminate flooring and opens to a private deck overlooking a tranquil wooded setting. The updated kitchen offers ample cabinetry with convenient rollout drawers, refrigerator, range, built-in microwave and dishwasher, with an adjoining dining area for everyday meals or entertaining. A built-in desk area provides a convenient dedicated workspace. The generously sized bedroom features a walk-in closet, and a full-size washer and dryer are conveniently located within the unit. Rollingwood offers a park-like setting with community amenities including a pool, clubhouse, tennis courts and playground. Ample parking adds to the convenience, while the location provides easy access to I-84 and Routes 7 and 202, as well as nearby shopping, restaurants and entertainment. A wonderful opportunity to enjoy comfortable, low-maintenanc

No expense was spared in this dramatic 3 bedroom 2.5 bath Townhome situated in the highly desirable Rivington, The Woodlands Collection. The open floorplan suits today's contemporary lifestyle with wifi controlled heating and A/C. Upon entering the townhouse one is met with Oversize windows in the living room allows for an abundance of natural light. The Incredible kitchen features tiled back splash, Granite Counters, Stainless Steel Appliances, farmhouse sink and Free Standing Center Island great for entertaining! Upstairs is a wonderful vaulted ceiling master bedroom with a master bath w/double vanity and walk-in oversized Glass Shower with a built in seat. Two additional vaulted bedrooms and laundry room complete this level. The back trex deck off the kitchen is perfect to enjoy al fresco dining. The garage comes complete with an electric car charger for your Tesla or other electric vehicle. Renting this unit gives you use of all the fabulous Rivington Club Amenities-3 pools, tennis

Looking for a quiet home in Montgomery with space to relax and grow? This 3-bedroom, 3-bath home at 68 Weaver Street offers a comfortable layout, thoughtful updates throughout, and a peaceful neighborhood feel—all within the Valley Central School District. This home comes with valuable upgrades including a renovated kitchen, updated roof, and finished basement, giving you peace of mind and move-in-ready convenience. The kitchen is designed for everyday cooking and gathering, while the upgraded roof and basement add long-term durability and flexible living space. Built for everyday living, this 3068 sq ft home sits on a oversized village lot, offering plenty of room for outdoor entertaining, gardening, or simply enjoying fresh air. Natural light fills the home during the day, and the layout creates a calm, comfortable flow for daily life. A whole house standby generator upgrade adds an extra layer of reliability, keeping essential systems powered during unexpected outages. Located in Or

Enjoy breathtaking lake and mountain views from this spacious 5-bedroom waterfront home available for rent in desirable Candlewood Lake Club community. Designed for comfort and entertaining, this exceptional property features two primary suites-one conveniently located on the main level and a second on the upper level-making it ideal for extended families or guests. The newer eat-in kitchen offers plenty of space for gathering, while the expansive recreation room with a pool table provides endless entertainment. Relax year-round in the screened-in porch or soak in the stunning scenery from the large deck overlooking the water. All lake club amenities included with rental, 9 hole golf course, tennis courts, pickleball and basketball courts, community beach and club house to name a few. Convenient commute location to major highways, nearby chops and restaurants. Available September 10, 2026-May 31, 2027 for $6000 per month. June, July, August 2027 is available for $60,000 total or $20,00

Experience the ultimate August retreat at 16 Anderson Acres Road, a contemporary masterpiece perched in the heart of Kent. This architectural gem is designed to blur the lines between luxury and nature, offering unrivaled panoramic views that stretch for miles from nearly every room in the house. Whether you are sipping your morning coffee in the open-concept living space or unwinding by the stunning pool, the breathtaking vistas of the Litchfield Hills serve as your constant, serene backdrop. The location offers a perfect balance of secluded tranquility and vibrant summer activity. You are within walking or biking distance to Lake Waramaug, where the best of lake life-from kayaking to sunset strolls awaits. Nature enthusiasts will also appreciate being minutes away from the lush trails and scenic beauty of Kent Falls State Park. When you're ready for a change of pace, the charming village of Kent is just a short 10-minute drive away, providing instant access to world-class art galleri

A Regal Sanctuary with recent key upgrades! Seize the opportunity to own a piece of majesty with this unparalleled castle perched atop a hill, commanding 60+ acres of pristine land. Surrounded by conservancy property, this estate promises uninterrupted tranquility and privacy. As you ascend the private road, the castle's imposing silhouette against the horizon is a prelude to the grandeur within. Boasting expansive living spaces, this 7,000+ sq ft residence offers endless potential for luxury and craftsmanship. The property's elevated position on the ridgeline affords breathtaking panoramic views stretching all the way to the Berkshires, ensuring every sunset is a spectacular event. The surrounding acreage, a mix of open spaces, ponds, woods and wild beauty, provides a serene retreat from the world. With nature as your neighbor, the possibilities are endless. There are trails for miles, an old mill, enjoy the local flora and fauna or simply bask in the peace that only such a secluded e

Beautifully renovated in 2011, this modern home in southern New Milford offers beach rights to Candlewood Heights Association. (Possible boat slip(additional charge). Though 1,110 sq ft, the home feels bright, open, and spacious with an airy layout guests love. The kitchen features stainless steel appliances and opens to a window-lined living/dining area overlooking wrap around deck. Enjoy central air, two stylishly tiled baths, and generous outdoor living with stone patios, gardens, landscape lighting, and an outdoor shower. Low-maintenance property with no mowing required. Ideal weekend retreat. Good credit required. No pets permitted

Candlewood Isle! One of the rare two bedroom + home office rental opportunities in the sought-after lake community and lovingly restored by the current owner. Upon entering, you are welcomed by a cathedral ceiling with exposed wood beams that make lake homes so desirable. The inviting stone fireplace serves as a beautiful focal point, creating the perfect setting to enjoy during the cooler months. The former screened porch has been thoughtfully transformed into a bright and elegant dining room, with windows that fill the space with natural light. Just beyond, a private deck offers the ideal setting for morning coffee or effortless summer entertaining. The main level features a spacious primary bedroom, an additional bedroom and a beautifully renovated kitchen designed for both style and functionality. The walkout lower level provides additional living space, including a home office/guest room, a full bathroom, and a comfortable family room with sliding doors that open to a charming sto

Newly renovated contemporary home in the heart of Washington is now available to rent for upcoming academic year: September 1, 2026-May 31, 2027. Drenched in natural light, this home is located on Wykeham Road, minutes from the Washington Green, Washington Depot and the Frederick Gunn School. The Leicht kitchen is a showstopper with superior European-designed cabinetry and white marble countertop boasting seamless, modern lines. High-end appliances compliment the sleek construction, including a Wolf wall oven, Gaggenau stove and oversized Thermador stainless fridge. White oak, wide plank flooring throughout adds to the crisp, clean style of the home. The open floor plan and designer lighting (Flos, Tom Dixon, Menu and Gobi) honors the simple but elegant character of this home. The en-suite primary bedroom graces the main level, with the second level offering 2 additional bedrooms and an office. Towering evergreen trees and mature perennial gardens envelop this home and give it a warm,

Enjoy the beauty of lakefront living during the academic year at this furnished waterfront home on the quiet end of Squantz Pond in Sherman, CT. Wake up to stunning water views and take a stroll to your private beach for swimming, kayaking, fishing, paddleboarding, or simply relaxing by the water. The home features a main-level primary bedroom with a full en-suite bath, an oversized deck with a barbecue grill, two kayaks and water toys, and ample off-street parking. Just minutes from restaurants and shopping in nearby New Fairfield and only 85 minutes from New York City, this peaceful retreat offers the perfect balance of comfort, recreation, and convenience. Academic-year lease preferred. Available beginning September 1, 2026

Welcome to Rivington, where resort-style living meets everyday comfort in this pristine tri-level townhouse with a one-car garage. Bright, spacious, and beautifully maintained, this home offers a luxurious yet inviting atmosphere throughout. The main level features 9-foot ceilings, hardwood floors, and oversized windows that fill the living space with natural light. The stunning kitchen is designed for both style and function, offering quartz countertops, stainless steel appliances, a large pantry, and an oversized island with seating. Sliders lead to the deck, while the kitchen flows seamlessly into the dining area and living room, creating an open-concept layout perfect for gatherings. Upstairs, the spacious primary suite features a vaulted ceiling, walk-in closet, and a private full bath with double vanity. Two additional bedrooms with vaulted ceilings, a full bath, and a convenient laundry area complete the upper level. The fully finished walk-out lower level offers 9-foot ceilings

Modern, Updated And Very Well Maintained 3 Bedroom Raised Ranch. Beautiful Property And Private With A Spacious Backyard. Modern Kitchen That Is Adjacent To The Large Family Room. Spacious Dining & Living Room. Wooden Floors Across The Home. Finished Basement With A Private Backyard. A Wonderful Rental Opportunity. Easy Access To Neighboring Towns & NYC

Own, live and/or potentially work in an important building from Newburgh's grand historical past! 98 Grand was built in the 1870s for a prominent member of the community with old newspaper clippings reporting fabulous soirees in the front parlor with mandolins, banjos and piano recitals. It was modified in the 1890s by the Newburgh Board of Education to include a staircase to the original Newburgh Library next door which still exists! Albeit as a bookcase now. The unusual and extraordinary front window likely also dates from the 1890s as does the magnificent front parlor. Modernized and beautifully updated over the years that followed, 98 is now a well maintained solid brick 4 unit building with 2 x 1 bed apts on the 2nd and 3rd floors with Hudson River views from their kitchens and bathrooms along with a convenient coin operated washer dryer on the 2nd floor. On the first floor there is a gorgeous spacious 2 bed apartment which still tells the story of its parlor days with its open pl

There is something truly special about a home that has watched the world change for over a century. Built in 1910, this captivating Colonial near Cornwall is a masterclass in early 20th-century elegance, updated just enough to offer the modern comforts we crave without losing an ounce of its historic soul. From the moment you step inside, the scale of the home makes an impression. High ceilings and gleaming hardwood floors set a grand tone, while ornate fireplaces serve as stunning focal points in the spacious living areas. Every corner reveals another piece of classic architectural craftsmanship that you just don't find in new builds today. The lifestyle here extends well beyond the interior. The grounds feature a beautifully landscaped backyard and a generous in ground pool area that feels like a private retreat. Inside, the layout is incredibly accommodating, offering six bedrooms across the upper floors and a vintage basement bar that’s practically begging for a cocktail hour