luxury houses for rent Western Connecticut Planning Region, United States

This exceptional stone residence, known as ''The Boulders'', is set atop 1.3 private acres,, seamlessly blending timeless architecture with modern comfort and convenience. Filled with natural light, the residence is defined by graciously scaled rooms, refined architectural detailing, and an effortless flow designed for both elegant entertaining and everyday living. The thoughtfully designed floor plan features a dramatic entry hall, a gourmet kitchen opening to an inviting family room, living, entertaining spaces, and a luxurious primary suite. Outdoor terraces and beautifully landscaped grounds create an idyllic setting for year-round enjoyment. A rare rental opportunity in one of Greenwich's most prestigious enclaves, offering historic character with modern amenities for easy living. Rental Terms: Annual: $24,000 Per Month

Redesigned for elevated living, this fully renovated 4-bedroom home combines open-concept style with seamless functional flow, offering near single-level living on a private, scenic lot. An inviting entry opens into an informal living room with a cozy fireplace, a high-impact great room featuring soaring cathedral ceilings, stylish beams, and French doors that flood the space with natural light. At the heart of the home, the chef's kitchen boasts exceptional counter space, professional-grade appliances, and a massive center island with seating for effortless entertaining or ease of everyday living. The main living space opens to a private wrap-around back porch with built-in corner seating & planters, perfect for outdoor relaxation overlooking the tranquil, tree-lined yard with an area for a garden.A separate wing houses the private primary suite-a serene retreat styled with shiplap walls, vaulted ceilings, large picture window, and spa-inspired bath complete with dual sinks, a freestanding soaking tub, a custom marble shower, and skylights. Three additional light-filled bedrooms and a full bath provide comfortable accommodations for guests or family.Complete with an attached 2-car garage, lower level flexible space and laundry, storage shed, and a lush, rolling lawn.This turnkey residence offers easy living just minutes from everyday conveniences, award-winning New Canaan schools, the Nature Center, Waveny Park, designer boutiques, NYC-inspired dining & the Metro North train Primary bedroom and guest bedroom both have 2 closets. Primary bath has shower stall and free-standing tub with a full-size linen closet. Interior has recessed lighting on dimmers throughout. 3-zones for heating & cooling.

INCLUDED ONE GARAGE SPACE! NEW Washer/Dryer Unit! Prime South Wilton location. Beautiful fully furnished 900SF one bedroom apartment/cottage. Family Room has fireplace with Dining Area, One Bedroom on 2nd floor, 1 full Bath on Main floor, and galley EFFICIENCY kitchen (no dishwasher) with plentiful open shelving. Large Office/Living Room space plus 3 closets. Tons of windows, doors and natural light. Peace and quiet on 2 acre property surrounded by mature plantings and lovely landscape. This is a very special opportunity!

Adorable 3-bedroom, 2-bath furnished cottage in sought-after Candlewood Lake community, offering an inviting open floor plan, main-level primary bedroom, and wood flooring throughout. The spacious screened porch - accessed from both the kitchen and living room - is the perfect place to relax and overlooks a private, level lawn and garden area. A detached shed includes a separate insulated room, offering flexible space for a studio, office, or retreat. Set on a quiet, level country road with little traffic, the property is ideal for walking and cycling. Enjoy access to Candlewood Lake from the town beach, along with an array of town amenities including kayak and canoe racks, a half-mile walking/jogging track, pavilion, playground, basketball court, and three tennis/pickleball courts. Sherman offers an exceptional blend of small-town charm and amenities, including a playhouse, expanded library, historical society museums, JCC community center, and local winery. Ideally located for commuting, the property is less than 90 minutes from Manhattan and is available for rent now through July 2027.

Enjoy living in the heart of Cos Cob's charming historic district from this hidden gem, tucked away on a tree-lined street, just minutes from all. The open kitchen and family room are ideal for gathering and flow seamlessly to both a breakfast area and a new deck and rear yard. A nearby dining room, living room with fireplace, and office/den with hardwood floors throughout offer flexible living spaces to suit your lifestyle. Upstairs, you'll find four bedrooms and two full baths, including a primary suite and beautiful, just refinished wood flooring. The finished lower level features a second kitchen, a spacious multi-use bonus room with new vinyl flooring, a third full bath, and a separate entrance perfect for work-from-home needs or multi-generational living. An unfinished laundry area and ample storage complete the space. The entire home has been thoughtfully refreshed with new paint, lighting, and appliances and the large barn can accommodate parking for two cars plus additional storage. Just steps from Metro North, the Water Club, library, harbor, schools, and Cos Cob's vibrant shops and restaurants, the property is set back in a way that offers privacy and room for play or entertaining but offers the convenience of in-town living. Note: January 2027 occupancy. Rental Terms: Annual: $9,895 Per Month

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen--all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private oasis awaits--an expansive deck overlooking the river, scenic landscaping, and a stone patio with gunite pool--perfect for summer relaxation or entertaining under the stars. In addition to the numerous recent improvements to the key systems of the home, the driveway has been redone and the house has been painted on the interior and exterior. This extraordinary property offers an unparalleled lifestyle in an idyllic setting.

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.

Hard-to-find short-term furnished 2 bedroom spacious rental now available through end of November in the Old Farms complex with wonderful views in New Milford. This rental offers a spacious primary suite with full bath and walk-in closet with slider access to the sun-drenched 3-season room. There is a 2nd bedroom with access to the second full bath. The Living Room with dining area also has access to 3-season room via sliders. Tastefully updated with fully equipped kitchen with stainless steel appliances, Corian countertop, with brand new flooring throughout the entire home! Enjoy lots of extra space for recreation, office and storage in the finished lower level (also furnished) and convenient laundry area. One of the only ranch units to have an expanded patio for grilling, a convenient parking space and end unit carport. Perfect location near everything New Milford has to offer along with surrounding New England towns and recreation.

Enchanting country cape/cottage in top location, just a short walk to historic Main Street for shopping, Ballard Park, library, theaters, restaurants, and more. Totally remodeled throughout with apprx. 1,000 sf, 2 bedrooms, 2 full baths, stone patio, level backyard, plus spacious, heated, attached garage. Generous proportions and open floor plan with large '10 x '20 living room featuring French doors to the adjoining dining room/kitchen. The large dining room offers atrium glass doors to the rear covered porch, patio, and picture perfect backyard with raised garden beds for planting. The totally remodeled kitchen showcases granite counters, center island with bar seating, and stainless steel appliances including gas range, microwave, dishwasher, and refrigerator. This special home also includes a main level laundry room with washer/dryer, plus an updated full bath on the main level with soaking tub. The upper level features a spacious primary suite with vaulted ceilings, charming paneled walls, and built-in shelving. The second floor also offers a second bedroom, large walk-in closet, and second updated full bath with skylight and frameless glass shower. Landlord to include mowing, plowing, leaves, gutters, and all grounds maintenance. Pets considered on case by case basis. Ready for immediate occupancy - nothing to do but unpack!

Elevate your lifestyle in this beautiful and modern 4-bedroom end-unit built in 2020 by Toll Brothers, complete with Rivington's resort-inspired amenities, simplified everyday living, and a coveted location in Western Danbury, directly on the NY/CT border. Maintained in pristine, barely-lived in condition, this Energy Star rated townhome boasts chic upgrades, gorgeous white oak floors, a tranquil wooded view, 9ft+ ceilings, and immense windows that flood the home with natural light. The open-concept main level offers a seamless, flowing connection between the family room, dining area, and a stunning chef's kitchen, which features quartz countertops and an oversized center island with ample seating.Sliding glass doors off the dining room open to an outdoor private deck. Perfect spot to unwind or grill dinner in a peaceful natural setting. Upstairs, the primary bedroom suite overlooks the quiet wooded backdrop and features a large walk-in closet and beautifully appointed bathroom with a dual-sink vanity and a luxe shower with seat. Two additional bedrooms offer large closets and a shared hall bath. A standout is a rare 4th bedroom with ensuite bathroom located downstairs on the entrance level. The separated space is ideal for guests or home office. The home is complete with a powder room, dedicated laundry area, extensive storage, and parking for four vehicles via the two-car garage and two-car driveway. Landscaping, snow removal, and trash/water/sewer are covered in the rent.

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.

CHARMING HOME LOCATED IN AN IN-TOWN ESTATE AREA. 3BR/2BATH WITH 1 CAR GARAGE. VERY PRIVATE YET CLOSE TO DOWNTOWN, TRANSPORTATION, LIBRARY, SHOPS AND RESTAURANTS. FIRST FLOOR WITH LIVING/DINING, KITCHEN, ATTACHED GREENHOUSE, FULL BATH AND LAUNDRY. SECOND FLOOR HAS 3 BEDROOMS AND A BATH. HARDWOOD FLOORS THROUGHOUT. Rental Terms: Annual: $6,250 Per Month

Your private retreat awaits. Situated to capture breathtaking, panoramic views of Candlewood Lake and the lush surrounding hills, this elegant estate offers the ultimate in privacy and peace. The expansive deck provides a flawless setting for sunset entertaining, while the interior layout-featuring 5 bedrooms and six bathrooms-offers flexible, well-designed space for any lifestyle. With the added luxury of 5 garage bays and grounds that promise total seclusion, this property represents the perfect harmony of nature and architectural refinement. Available furnished on a month-to-month basis, for the summer, or longer!

Escape to your own private sanctuary in this sun-filled, flexible layout home located in the highly desirable In-Town neighborhood, close to all of Westport's amenities. Offering a rare blend of dramatic natural beauty and everyday convenience, this property features breathtaking, unobstructed views of a waterfall on Lee's Pond, which flows directly into the historic Saugatuck River. This is a 5-bedroom house (3 bedrooms have the waterfall view) with an upstairs playroom. 2 of the 5 bedrooms have their own den area and a full bathroom-including a back staircase providing a separate living area with great privacy and independence for guests, an au pair, or in-laws. Launch your kayak right from your backyard and enjoy a scenic paddle directly into vibrant downtown Westport. Enjoy shopping, dining, and community events just minutes away. Host unforgettable summer cookouts on the patio while relaxing to the serene, soothing sounds of the waterfall.

Escape to your own private sanctuary in this sun-filled, flexible layout home located in the highly desirable In-Town neighborhood, close to all of Westport's amenities. Offering a rare blend of dramatic natural beauty and everyday convenience, this property features breathtaking, unobstructed views of a waterfall on Lee's Pond, which flows directly into the historic Saugatuck River. This is a 5-bedroom house (3 bedrooms have the waterfall view) with an upstairs playroom. 2 of the 5 bedrooms have their own den area and a full bathroom-including a back staircase providing a separate living area with great privacy and independence for guests, an au pair, or in-laws. Launch your kayak right from your backyard and enjoy a scenic paddle directly into vibrant downtown Westport. Enjoy shopping, dining, and community events just minutes away. Host unforgettable summer cookouts on the patio while relaxing to the serene, soothing sounds of the waterfall.

THIS HANDSOME WHITEWASHED BRICK AND SHINGLE COLONIAL IS BEAUTIFULLY SITED ON A LEVEL, ONE ACRE PARK-LIKE CUL-DE-SAC SETTING. BOASTING A TRADITIONAL LAYOUT WITH FRONT TO BACK RECEPTION HALL, LIVING ROOM AND FAMILY ROOM WITH FIREPLACES, AN UPDATED GOURMET KITCHEN WITH ISLAND, FORMAL DINING ROOM AND STUDY. THE FAMILY ROOM OPENS TO FLAGSTONE TERRACE THROUGH THE FRENCH DOORS. ENJOY FLAT YARD WITH SWEEPING LAWNS AND MATURE TREES. BRIGHT PRIMARY BEDROOM SUITE WITH UPDATED PRIMARY BATHROOM. 3 ADDITIONAL BEDROOMS AND 2 BATHS ON SECOND FLOOR. 2 CAR ATTACHED GARAGE. THE TENANT PAYS FOR THE GROUNDS AND THE LANDLORD WIL PAY FOR THE SPRING AND FALL CLEAN UP. Rental Terms: Annual: $15,000 Per Month

Welcome to this newly renovated 4-bedroom, 3-bath home on a quiet street in highly desirable South Wilton. The home offers a bright, open layout ideal for everyday living and entertaining, highlighted by a large family room with vaulted ceilings and abundant natural light. The newly updated kitchen features Quartz countertops, all new appliances, a large center island, and modern finishes, and opens seamlessly to the main living and dining areas. Upstairs, the primary suite includes a wall of built-in closets, a newly renovated bath with double vanities, and sliding doors to a Juliet balcony. Two additional bedrooms and a second full bath complete the second floor, while a second en-suite bedroom with new full bath offers excellent flexibility for guests, work-from-home space, or extended family. Floors have been resurfaced throughout, and the home offers excellent storage. The lower level features an oversized playroom or second family room with sliders to a screened-in porch with vaulted ceiling and access to the deck, perfect for outdoor entertaining. Additional highlights include a two-car attached garage, laundry room with brand-new washer and dryer, new central air conditioning, new heating boiler and water heater, whole-house propane generator, new garage door, and new septic system. Conveniently located close to Wilton and Westport town centers, award-winning schools, shopping, and commuter routes. Move-in ready and available for immediate occupancy.

Charming 3-4 Bedroom Rental in Desirable Darien Water Community - $5,800/month Welcome to this inviting 3-4 bedroom, 2 full bathroom home in a sought-after Darien water community. Perfect for families or anyone seeking a blend of comfort and coastal living, this well-maintained residence offers flexible space to suit your lifestyle. The private, fenced-in backyard provides a safe haven for the family and pets to play, while also creating the perfect setting for outdoor dining and relaxation. Enjoy easy access to Holly Pond-just a short walk from your door-where you can embrace the waterfront lifestyle that makes Darien so special. This home combines practical living spaces with the lifestyle you've been dreaming of, all in one of Fairfield County's most desirable communities

All-inclusive furnished rental. Available: Winter- 3 month min. $8000/month. Summer Season- Memorial Day thru Labor Day $65,000/season. Summer monthly- $25,000/month. Escape to the serene countryside and experience the authentic charm of this beautifully renovated antique home with a refreshing, heated pool. This rental is fully equipped and all-inclusive with bi-weekly housekeeping. Step inside and discover the beauty of a historical Colonial home, thoughtfully updated with modern comforts. The rooms offer plenty of space and showcase exposed beams and vaulted ceilings. You'll appreciate the natural touch of hardwood floors and the convenience of five fireplaces for those cooler evenings. Stay comfortable all year long with central air conditioning ensuring a pleasant stay in any season. The heart of the home is a charming country kitchen, providing an ideal space for cooking up delightful meals. It opens onto a stone patio, inviting you to enjoy the outdoors with relaxed gatherings. Take in the tranquil views of the countryside as the property sits on level open land adjacent to a land trust. You'll find all the local amenities you need nearby, including a variety of recreation and cultural venues, shopping and fine dining options. 60 minutes to lower Fairfield County, NYC is 90 minutes.

All inclusive Furnished rental available 9/5/2025. Escape to the serene countryside and experience the authentic charm of this beautifully renovated antique home with a refreshing, heated pool. This rental is fully equipped and all-inclusive with bi-weekly housekeeping. Step inside and discover the beauty of a historical Colonial home, thoughtfully updated with modern comforts. The rooms offer plenty of space and showcase exposed beams and vaulted ceilings. You'll appreciate the natural touch of hardwood floors and the convenience of five fireplaces for those cooler evenings. Stay comfortable all year long with central air conditioning ensuring a pleasant stay in any season. The heart of the home is a charming country kitchen, providing an ideal space for cooking up delightful meals. It opens onto a stone patio, inviting you to enjoy the outdoors with relaxed gatherings. Take in the tranquil views of the countryside as the property sits on level open land adjacent to a land trust. For moments of relaxation, take advantage of the outdoor pool, a refreshing oasis on warmer days. Annual rental $10k per month, academic term $8k per month, winter 3 month minimum $8k per month. You'll find all the local amenities you need nearby, including a variety of recreation and cultural venues, shopping and fine dining options. 60 minutes to lower Fairfield County, NYC is 90 minutes.

Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for the 2025 summer season or by summer month. Scenic distant views frame this private 15-acre compound. Elegantly presented interiors, with extensive renovations supervised by an AIA architect specializing in historic preservation. Attention to detail and quality is evident throughout the home. The main level offers a warm and welcoming country kitchen/dining room with oversized island, high end appliances and finishes. There is also a charming living room, spacious family room (each with fireplace), a small office and a partially-screened wraparound porch. Four bedrooms and 2.5 Baths are offered on the upper level, including a wonderful primary bedroom suite with fireplace, full bath and dressing room. Additional accommodation is available in the newly finished guest house encompassing a living area, plus bedroom, kitchen and bath. Outside are patios, terraces, stunning gardens, stone walls and chickens (!) along with an inground gunite pool and hardcourt tennis court. Beyond the property's large private pond are the distant country views that help to create this most peaceful country setting. Available for the month of June for $18,000 or July at $20,000 per month.

Luxurious Federal Colonial Rental in Prime Darien Location. Welcome to this stunning 4-bedroom, 4-bath custom-built home, designed by an award-winning architect, and nestled in one of Darien's most sought-after neighborhoods. Just a short walk from the train station, town center, parks, and Royle Elementary School, this exquisite property offers the perfect blend of historic charm and modern luxury. Completed in 2016, this home embodies the timeless elegance of Federal Colonial architecture while offering all the modern amenities you desire. Set on a private half-acre lot, the residence features an open-concept floor plan with high ceilings and beautiful millwork throughout. The spacious family room, with its wood-burning fireplace and French doors, opens to a patio and generous yard-ideal for both relaxation and entertaining. The gourmet eat-in kitchen is a chef's dream, equipped with Viking and Bosch appliances, a marble-topped island, and a large walk-in pantry. Adjacent to the kitchen, the mudroom offers a secondary entrance for convenient access and additional parking, along with sidewalks leading to Darien's vibrant downtown and the newly developed Corbin District. The home's layout is designed for comfort and privacy. The primary suite, located on the second floor, serves as a luxurious retreat with dual walk-in closets and a spa-like ensuite bath. Two additional bedrooms on this level share a well-appointed Jack and Jill bathroom, and a large laundry room.