luxury properties for rent Connecticut, United States (page 2)

A Timeless Summer Tradition: Renovated Victorian Shingled beach house in the Borough of Fenwick Experience the quintessential New England summer in the historic Borough of Fenwick. This stunning, shingle-style Victorian beach house seamlessly blends old-world coastal charm with modern, high-end luxury. Featuring 8 spacious bedrooms and 4.5 baths, this expansive residence is the perfect sanctuary for large families or those who love to entertain against the backdrop of the Long Island Sound. The heart of the home is a totally renovated gourmet eat-in kitchen, designed for the culinary enthusiast and large-scale hosting. Beyond the kitchen, life slows down on the magnificent wrap-around screened porch-the perfect vantage point to enjoy your morning coffee or an evening cocktail while overlooking the water and catching the sea breeze. Retreat to the third floor, where a dedicated playroom offers a private escape or a quiet workspace away from the main living areas. From its cedar-shingled exterior to its thoughtfully updated interior, every inch of this home invites you to relax, recharge, and rediscover the magic of a Fenwick summer.

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.

Experience the quintessential summer lifestyle in this light-filled 2-bedroom, 2-bathroom modern beach cottage, designed for those who value sunshine and salt air. Perfectly situated just steps away from private beach access, this home is the ultimate retreat for relaxation and coastal adventure. A private oasis for summer BBQ's on the beautiful deck, central air, Newly renovated. Outdoor shower for when you return from the sandy beach. AVAILABLE JUNE - $7,000, JULY - $10,000, AUGUST - $10,000

RESERVE YOUR MONTH AT THE BEACH IN MADISON ! RELAX IN THIS VINTAGE 3-BEDROOM DORMERED CAPE W/ STUNNING SCREENED PORCH ~ SET IN PRIVATE SANDY BEACH COMMUNITY A SHORT WALK TO THE BEAUTIFUL WAVES OF LONG ISLAND SOUND ~ HOME IS PRESENTLY AVAILABLE FOR THE FULL MONTH OF JULY

A quiet country lane near the Lake Club (pool lake and tennis club) introduces this lovely Colonial set back on a beautiful, level property. The desirable open floor plan encompassing a warm and inviting kitchen and family room w/ a stone fireplace encourages lingering and relaxation. The gracious living room also with a fireplace and an expansive dining room are perfect for more formal entertaining. A large bonus room, 1st floor office, laundry and mudroom complete this level. The master suite enjoys a full bath and walk-in closet. Down the hall are three additional bedrooms and large hall bath. Finished walk-out lower level. Convenient location.

Rental Available August 25, 2026- June 15, 2027 An incredible East Rock opportunity. This magnificent 5 BR furnished home is available for academic rent. An elevator takes you to all 3 floors of this amazing home as well as down to the full dry basement perfect for storage. Main floor boasts a Living room, dining room, a huge kitchen that opens to a family room as well as a big deck that leads to a fully fenced in private yard. The second floor has 4 BR's, one with built-ins doubles as a great home office.2 full beautiful new baths. The third floor is fabulous! A private family room, loft, huge bonus room, a bedroom and new beautiful bathroom. Tons of built in bookshelves throughout. Gas heat, central air. Located in the private corner of Everit street across from the park with off street parking. Minutes to Foote school and a short walk to Yale and Downtown New Haven. No smoking. No pets. 700 Minimum credit score. LISTING AGENT MUST BE AT ALL SHOWINGS AND TIMES ARE LIMITED SO PLEASE GIVE PLENTY OF NOTICE Rentspree Application Accepted

STILL AVAILABLE FOR LAST TWO WEEKS OF AUGUST! Panoramic vistas of Long Island Sound and the East River create a breathtaking backdrop for this sophisticated Madison waterfront retreat. Designed for elevated coastal living, the sun-drenched open floor plan flows effortlessly from the main living spaces to expansive water views beyond. Offering 3 bedrooms and 3 full baths, the home comfortably accommodates 8+ guests with thoughtful design and generous gathering spaces. Enjoy easy access to shoreline beaches, perfect for morning swims and evening strolls along the water, while the private heated pool provides a serene setting for long summer afternoons under the Connecticut sky. Available weekly for the last TWO weeks of August at $8,000 per week. A rare opportunity to experience Madison's shoreline lifestyle at its finest - where timeless waterfront beauty meets effortless summer luxury.

FURNISHED RENTAL AVAILABLE - September 1, 2026 to May 31, 2027. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on 1st floor, sunny year round office on the south side of the home, and outdoor shower. Walk / bike to downtown Madison. No smoking permitted. NO PETS. Credit check and security deposit required.

Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for kicking back and soaking in the expansive views! The third floor is a private retreat with the seventh bedroom and enormous recreation room. Let's also remember the large, water-facing screened-in porch perfect for soaking in the sunrise and sunset each day. Just outside, sun, sand, and saltwater air await you! This is the perfect place to be this summer - schedule your private viewing today and enjoy your own private beach in a few short months! One month for $45,000, two weeks for $22,500 or one week for $12,500. Please reach out to listing agent for most up-to-date availability.

SEEKING A 3 BEDROOM FULLY FURNISHED ACADEMIC RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to a renovated full bath and oversized Kitchen. The three bedrooms are on the 2nd floor with a hallway full bath. The neighborhood is one of the most sought after in Madison; Assoc beach is 2 minute walk, surrounding streets provide plenty of walking / running opportunities, neighborhood is quiet and quaint. The home is close to Town, close to I-95 and easily accessible to all other amenities the Town has to offer. House is available from September 15, 2026 to May 15, 2027.

Sharon, CT - Nature is your neighbor in this welcoming 3BR/1.5BA home tucked among tall trees and rolling hills for tranquil, picture-perfect living. Enter via an open kitchen with ample cabinets and counter space, plus a brand-new energy-efficient wood-burning stove. Adjacent is the airy living room with cathedral ceiling and skylights that flood the space with natural light. Beside the Livingroom, the first-floor primary bedroom enjoys its own private outdoor entrance. The main level also includes a full bath with linen closet, a laundry room, and a storage room. Upstairs are two generous bedrooms with large closets and a spacious half bath with linen closet. Propane utilities and the wood stove help keep heating costs low. Live peacefully in Sharon with hiking minutes away at Sharon Land Trust and the Sharon Audubon Center, and performances at the Sharon Playhouse. Swim at Mudge Pond; shop local at Sharon Market; enjoy meals at Troutbeck, Le Gamin, Pigs Fly South, or light fare at JP Giffords. Engage the community at Hotchkiss Library. You're ~10 minutes to Sharon center and ~5 minutes to Cornwall Bridge, with a hospital in town. Nearby villages-Millerton, Cornwall, Kent, Lakeville, and Salisbury-offer charming cafes, antiques, waterfalls, trails, private schools, and Lime Rock Park (Millerton is within 10 miles). Explore art at Standard Space (Sharon), Geary Contemporary (Millerton), and the Wassaic Project. Your new home awaits!

RESERVE YOUR MONTH AT THE BEACH IN MADISON ! RELAX IN THIS VINTAGE 3-BEDROOM DORMERED CAPE W/ STUNNING SCREENED PORCH ~ SET IN PRIVATE SANDY BEACH COMMUNITY A SHORT WALK TO THE BEAUTIFUL WAVES OF LONG ISLAND SOUND ~ HOME IS PRESENTLY AVAILABLE FOR THE FULL MONTH OF JULY & THE FULL MONTH OF AUGUST

This historic Victorian home in the New Preston section of Washington is now available to rent after a tasteful top to bottom renovation, and the addition of a heated saltwater pool and hot tub. The main level of the home is highlighted by the expansive kitchen with soapstone counters, a butler's pantry, and French doors leading to a rear patio area. The remainder of the first floor features a living room, spacious great room, dining room, and an office with a full bath that could be used as a 5th bedroom. Upstairs are 4 bedrooms, each named after prior owners who have called The Humphrey's House home over the past 127 years, including a nephew of Mark Twain. The bright and sunny primary bedroom has a stylish walk in closet, and an en-suite bathroom with a steam shower and radiant heat flooring. A brand new bathroom in the second en-suite bedroom features the same top of the line upgrades. Two additional cozy bedrooms sit across the hall, with a third second level bath serving the two rooms. Well known British designer Graham Robert Moore has transformed this Victorian gem into a marvelous display of the modern day aesthetic without abandoning the history of the home. The 40 x 18 heated saltwater pool features an electric cover and 8 person attached hot tub. This gorgeous house is just a short stroll to swimming and boating at Lake Waramaug, shopping in the New Preston town center, 30 minutes to Metro North trains and 90 minutes from Manhattan! August offered at $40,000. First week of September is also available at a pro-rated price.

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original porthole windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor flex space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches and expansive patio for gatherings. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!

Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for July and August 2026. 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 two 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 detached 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 months of July and August at $20,000 per month or $36,000 for both months.

Summer furnished rental! Come out to the country and enjoy this beautifully updated, spotless and spacious colonial style home, fully furnished for all your needs. Plenty of room to work remotely (upstairs or on the first floor) and a large level backyard to enjoy the outdoors. Enclosed porch and large patio overlooking gorgeous and private back yard. Convenient to Wilton center, take a train to NYC, enjoy Merwin meadows lake and playground with the little ones, 15 minutes to Westport beaches or walk the Norwalk valley river trail. Room for four people to relax and enjoy the summer months. First floor has living room with fireplace, office with beautiful windows to view the outdoors, stunning new eat in chefs kitchen as well as formal dining room. Large family room is bright with cathedral ceiling and two desks for remote learning. Finished lower level recreation/play room has ping pong table and play area. Term is flexible!

Central air conditioning, in-unit washer/dryer, AND a garage- the perfect trifecta for this beautiful sunlit rental. Occupying the entire upper level of a charming farmhouse just north of downtown Westport, this spacious 980-square-foot home combines modern convenience with historic character. Step inside to discover a newly renovated eat-in kitchen with sparkling finishes and beautifully restored antique floors that add warmth throughout. The generous living room provides ample space for relaxing and entertaining, while the large bedroom includes a convenient office alcove-ideal for working from home. Nestled in a lovely neighborhood, you're just over a mile from Westport's vibrant downtown dining and shopping scene-an easy walk or quick drive. Commuters will appreciate the train shuttle stopping right at your door, making the NYC commute effortless. Landlord covers landscaping, water, and trash removal. This welcoming apartment offers the rare combination of character, convenience, and location. Easy to show.

AVAILABLE FOR THE MONTH OF AUGUST. Embrace Coastal Serenity in a Fully Renovated 5 bedroom, direct waterfront Estate WITH ITS OWN PRIVATE BEACH! Discover the epitome of waterfront luxury in this exquisite Clinton, CT residence, where historic charm meets modern elegance. Nestled on a generous .51-acre lot, this multi-level home boasts of a direct waterfront access with plenty of privacy. Built in 1912 and meticulously renovated along the way. Experience the perfect blend of timeless architecture and contemporary updates. A spacious primary suite (with private balcony!) and two additional bedrooms on the second floor, plus two bedrooms and a rec room on the third floor, provide ample space for family and guests. Step outside to enjoy multiple decks with a panoramic view of Long Island Sound and private beach access for tranquil waterfront living. A spacious Living Room with a fireplace, formal Dining Room, light filled Great Room, and a Sunroom offer diverse areas for relaxation and entertainment. This property is a rare gem, offering a waterfront lifestyle coveted by many but enjoyed by few. Whether basking in the warmth of your fireplace or soaking up the sun on your private beach or deck, this home is a sanctuary for those who seek a blend of luxury and tranquility. It's the perfect home for a month retreat!

AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms- one king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

AVAILABLE FOR MONTH OF JULY. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms- one king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

AVAILABLE FOR THE MONTH OF JULY 2026. SEEKING A 4 BEDROOM FULLY FURNISHED SUMMER RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to a renovated full bath and oversized Kitchen. The three bedrooms are on the 2nd floor with a hallway full bath. The neighborhood is one of the most sought after in Madison; Assoc beach is 2 minute walk, surrounding streets provide plenty of walking / running opportunities, neighborhood is quiet and quaint. The home is close to Town, close to I-95 and easily accessible to all other amenities the Town has to offer.

The Connecticut coastal lifestyle awaits you - an incredible opportunity to live in Darien on the Five Mile River Road across the street from the water! This charming New England colonial has been completely renovated featuring 4 bedrooms, and 3 full baths, situated on a private hilltop with views, and a large flat backyard. Located in a highly sought after neighborhood with top rated schools, this home features a gorgeous new kitchen with new appliances and flooring, new bathrooms, new central air, new windows, lighting and a new roof! The primary suite is dreamy and offers a fireplace, full bath, and an adjacent dressing room (or office), and water views. Plenty of natural light throughout the house. A formal dining room off of the living room, a breakfast room with wood beams off of the kitchen, and a sunroom/family room that opens onto a lovely stone terrace for outdoor dining. Updated back entrance mudroom area with storage. Two working fireplaces, a wood paneled library/music room/den complete with built in bookshelves and built in bar-perfect for entertaining! The house is ready to move in with immediate occupancy available. Pets upon approval. Convenient to both Darien and Rowayton train stations, with shopping and restaurants and all amenities close by.

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. July and August 2026. Also available September 15, 2026 - May 31, 2027 for 3K per month.

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. Available September 15, 2026 - May 31, 2027. Also July and August at 6K per month.

STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a comfortable and chic look. Long distant views and rolling, verdant lawns add to the magic of this property. Close to top restaurants, art galleries, shopping and outdoor recreation. Only 90 minutes to NYC. Note: Field card indicates that there are 3 bedrooms but the house has 4 bedrooms and a 1250 tank.