luxury house with pool for rent Egremont, United States

Available from September 15 - May 15 2027 for $8k per month. Gorgeous Barn Style Home that is both stylishly decorated and cozy. Metro North Wassaic train station is just 15 minutes away for great access to NYC! Quiet and private 10 acre setting with heated gunite pool, level land for play, just minutes from both Kent and Sharon Centers in the highly desirable Ellsworth area of Sharon. Open Floor Plan with high ceiling, bright and airy rooms. Patio for great entertaining. Game Room with pool table. 30 ft Granite Fireplace with Beamed ceiling in Living Room. Gourmet Kitchen, 6 bedrooms, one on the first level, 4 En suite. 2 half baths. Private guest or in law apartment. Separate playground, large wooden deck ideal for relaxing. Beautiful Pastoral Area.... The ultimate in Vacation Homes!

Available now for yearly rental. Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Do you enjoy hiking or cross country skiing? Explore the homes 142 acres. Fall foliage is right around the corner followed by ski season. Mohawk Mountain a short distance away, or ski The Berkshires in a hour. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. There is easy access to Litchfield County's many private schools. Enjoy the hiking trails at local land trust, canoeing or kayaking on the Housatonic river or Lake Waramaug. There are country fairs, art shows, local theatre, great restaurants and many fine shops to explore. Available now for $10,000 per month for yearly lease. Call for Summer or Winter Rental pricing. Minimum 24 hour notice to view.

Welcome to 3 Old Shop Road—a timeless yet beautifully updated farmhouse that captures the essence of relaxed country living. Set on a sprawling, storybook property with lush lawns, mature trees, and a sparkling pool, this five-bedroom, five-bath residence offers the perfect blend of character, comfort, and charm. From the moment you arrive, you'll feel the magic of this home's setting—ideal for hosting garden parties, family gatherings, or intimate dinners beneath a canopy of trees. The outdoor spaces are a dream: a stone patio for summer entertaining, expansive grounds for play and leisure, and a pool that invites long, languid afternoons. Inside, the home balances antique soul with modern ease. The heart of the house is the kitchen—warm and welcoming with custom cabinetry, a relaxed layout, and a farmhouse table that invites conversation. The living room is anchored by a handsome fireplace and bathed in natural light, perfect for cozy evenings and lively weekends alike. The first-floor primary suite is a true retreat, featuring its own fireplace and direct access to the stunning grounds—so every morning feels like waking up in a private park. Rich in charm and tailor-made for modern living, 3 Old Shop Road is a rare offering in the coveted Cross River community.

Lovely Madison Colonial located on a beautiful cul-de-sac available as of September 16, 2026 for annual, academic or monthly rental. The 1st floor features a pretty kitchen, open family room with fireplace, formal dining room, living room, powder room and bedroom with a full bath. The 2nd floor features a nicely sized primary bedroom with full bath, 2 additional bedrooms and a hallway full bath. The 3rd floor features an additional room that can work as additional guest space or an office. Downstairs you'll find a partially finished area perfect as a playroom or hang out room. Enjoy the change of seasons on the front porch swing or sitting on the private back deck. Take a dip in the above ground pool (open seasonally) or bike around the neighborhood. A terrific house at a terrific price! Tenant pays for ALL utilities. Landlord covers mechanicals, septic and taxes. Excellent credit score required. Non-smoking. No pets.

Fully Furnished Seasonal Rental in Westport - Fall 2026 through Spring 2027 Fully furnished contemporary home located on a quiet cul-de-sac, minutes from downtown Westport, beaches, and restaurants. Offering 4 bedrooms, 3 full bathrooms, and 4,711 sq ft of living space, this home features an open floor plan with high ceilings, oversized windows, and a double-sided brick fireplace. The property includes a fully equipped kitchen with stainless steel appliances, gas range, and heated wood floors, a formal dining room, two living areas, and a welcoming foyer with a piano. The lower level offers a recreation room with ping pong, toys, books, and fitness equipment, while the primary suite features a soaking tub, heated floors, and a walk-in closet. Additional amenities include central air, an attached two-car garage, public utilities, a porch, deck, gas grill, outdoor seating, and a full-house automatic backup generator. Close to Sherwood Island State Park, golf courses, tennis courts, and town amenities. Available for Fall, Winter, and Spring 2026-2027 with flexible lease dates. Liability/renter's insurance with a minimum of $500,000 coverage required.

Is this Westport or Provence? Sited high above Greens Farms is this charming and spacious renovated cottage on a prime, flat and open estate property. A water lover and swimmer's dream, with stunning, large heated pool (with kick pads) and spa (seats 8+). All-new gourmet kitchen, newly finished pickled wood floors, fresh paint throughout. Decorated for stylish and comfortable living, it's the perfect place to call home. Sunny living room, spacious family room with fireplace and wet bar. Private setting, away from main house. Walk to Greens Farms train station, quick bike ride to Burying Hill beach. Organic garden onsite with fresh herbs and occasionally vegetables available too! Full pool and spa privileges. See floor plans in attachments.

AVAILABLE EARLY SEPTEMBER TO THE END OF MAY, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

CONNECTICUT CLASSIC, FULLY FURNISHED CENTER-HALL COLONIAL, GRACIOUS FOYER WITH COFFERED CEILING LEADS TO FORMAL L/R. FAMILY ROOM OFF KITCHEN FOR GREAT FLOW, CHERRY-WOOD LIBRARY, KITCHEN WITH GRANITE COUNTERS, SPACIOUS EAT-IN AREA, AND TOP OF THE LINE APPLIANCES. DOUBLE FRENCH DOORS OPEN TO NEW MAHOGANY DECK OVERLOOKING THE POOL AND 4 ACRES OF OPEN MEADOW. L/L FEATURES PLAYROOM, L/R WITH F/P + KITCHENETTE AREA AND LARGE GUEST SUITE W/ BATH AND LAUNDRY, GREAT FOR GUESTS WITH PRIVATE ACCESS/ENTRY. UPPER FLOOR HAS LARGE PRIMARY SUITE WITH F/P, LUXURY PRIMARY BATH, OFFICE AREA. 3 ADDITIONAL BR, 2 STONE & MARBLE BATHS, WHIRLPOOL TUB, LAUNDRY ROOM, COMPUTER/LOUNGE AREA. PETS MAY BE APPROVED ON A CASE BY CASE BASIS. 3 MONTH MINIMUM TERM. Rental Terms: Annual: $31,500 Per Month

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June $25,000; July 1-23 $27,000 (RENTED); Aug 1-15 $20,000; Sept 9-30 $18,000. Permit #1230.

2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedrooms—including a luxurious primary en-suite—and 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.

2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

Welcome to this one of a kind, completely renovated, estate in Matinecock with inground heated pool on a park like property. The main house features a large living room with fireplace, formal dining room with fireplace and a sun room open to the garden and patios. The brand new EIK is perfect for family and entertaining. Upstairs is a large primary with fireplace and new primary bath featuring double sinks, bath and shower. There are two additional bedrooms and a new hall bath. The third floor offers a bonus room and the basement is finished. Through a breezeway you access the 1 bedroom cottage that has a kitchen and full bath. The heated free form pool has its own outdoor shower and toilet. The perfect retreat in the country!, Additional information: Appearance:Mint,Interior Features:Guest Quarters

2026 Rates: June $8,500/week; July and August $10,000/week (Two Week Minimum For All Rentals). Spend your summer in style at this exquisite brand-new modern farmhouse, offering the perfect blend of luxury, comfort, and North Fork charm. Located just minutes from Greenport Village, local farmstands, renowned wineries, and pristine beaches, this home is the ideal summer retreat. Set on a full 1-acre lot, this spacious and sun-filled residence features an open-concept layout with elegant hardwood floors throughout. The heart of the home is a high-end chef’s kitchen, fully equipped for entertaining and flowing seamlessly into a stylish living area complete with a gas fireplace—perfect for unwinding after a day on the Sound. The first-floor primary ensuite bedroom offers a serene private escape, while the second floor includes a junior ensuite and two additional guest bedrooms with a shared full bath—providing ample space and comfort for family and friends. Step outside to your own private oasis featuring a 20x40 heated in-ground pool, surrounded by lush landscaping and plenty of space for outdoor dining and lounging. Whether you’re sipping wine under the stars, enjoying a day at the beach, or exploring nearby Greenport’s vibrant shops and restaurants, this stunning farmhouse offers the ultimate summer experience.

2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy ambiance and an abundance of natural light. The home boasts stunning hardwood floors and is elegantly appointed with multiple living areas that provide the perfect balance of open space and private retreats. Ideally situated within walking distance of Kenney’s Beach, you’ll find yourself just moments away from charming local cafes, unique boutiques, renowned wineries, and exceptional dining options. This North Fork gem is truly the ultimate summer haven. Don’t miss your chance to experience the perfect blend of comfort and convenience!

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

Escape to the heart of the North Fork in this beautiful, spacious four-bedroom home, perfectly designed for entertaining and hosting. Inside, you'll find ample living space complemented by a fully finished basement—ideal for extra lounging or movie nights—while the private backyard oasis features a sparkling heated pool for endless summer fun. Centrally located just one mile from Breakwater Beach, this home offers unbeatable access to the very best of the region, putting you just minutes away from the charming shops on Love Lane, premier local vineyards, and acclaimed farm-to-table restaurants. Book your stay today and secure the perfect central base for your ultimate retreat!

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. Beautifully updated 4-bed, 4-bath home offers private 20x40 heated saltwater pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor & outdoor dining. The expansive master suite boasts breathtaking views, king-size bed, office nook, dressing area, full bath, and private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Offered Apr $11,000; May $20,000; June $25,000; July $35,000 (RENTED); July 31-Aug14 $20,000; Aug15-Sept 8 (RENTED); Sept 10-30 $20,000; Oct $20,000; Nov $15,000. Permit# 0234.

Nestled on a quiet cul-de-sac in the prestigious village of Old Brookville, this stunning Mediterranean style estate offers the ultimate in luxury rental living. Set on 2 beautifully landscaped acres, this private, resort like retreat combines elegance, space, and exceptional amenities. With over 5,100 square feet of living space, this home features a large foyer that opens into a sophisticated and inviting living room, flowing seamlessly into a large formal dining room perfect for entertaining. The eat-in-kitchen is equipped with top-of-the-line appliances, granite countertops, and custom cabinetry, ideal for both everyday living and hosting. The residence offers 6 spacious bedrooms, including four on the main level and 2 on the lower level, along with four full bathrooms and two half bathrooms from which 3 are updated. The primary suite serves as a private sanctuary with a en suite bath and walk-in closet, while additional bedrooms provide ample natural light and generous storage. The outdoor setting is equally impressive, featuring a private tennis court, and heated swimming pool with spa, all surrounded by lush, manicured grounds. A spacious patio overlooks the serene flat property, creating the perfect backdrop for relaxation or entertaining. Offering exceptional privacy and tranquility while remaining conveniently close to shopping and dining, this is a rare opportunity to experience luxury living in one of Long Island’s most sought after locations. For added convenience and flexibility, the home is available for rent either fully furnished or unfurnished, allowing tenants to choose the option that best suits their lifestyle.

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. 2026 Pricing: July $30K | Aug-LD $35K

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.