luxury houses for rent Old Saybrook, United States (page 2)

Private, recently renovated, arts and crafts style ranch located in the heart of Orient Village. Three bedrooms, 2 full baths, open kitchen/ living room/ dining room, library, front porch, rear deck with screened outdoor dining area & grilling station. Close to beaches, marinas & village amenities. Offered Aug $15,000. Permit #0505.

Impeccably restored and updated 1850's Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Offered June $20,000; July $45,000; Aug $45,000; Sept $25,000. Permit # 1019.

Step into summer in Orient this year. Relax and rejuvenate in the quiet soundfront beach community of Orient by the Sea. The sunny open concept floor plan with sliding glass doors leads out to the covered backyard deck and invites indoor and outdoor entertaining. Just a short drive away to Greenport's many restaurants, the area's popular wineries for a tasting, or take a bike ride to Orient Beach State Park for a peaceful day on the bay. Permit #0863

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16 x 32 heated pool, newly renovated chef's kitchen and baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to a Willow Terrace bay beach. Embrace the North Fork lifestyle. Permit #0516

Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and large fenced in yard. Three bedrooms and full bath on the 2nd floor. Located on a quiet road but still close to beaches, farm stands and local vineyards! $6,500 per week. 2 week minimum.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692.

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. This beautifully updated 4-bedroom, 4-bathroom residence offers a private 20x40 heated saltwater in-ground pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor and outdoor dining. The expansive master suite boasts breathtaking views, a king-size bed, an office nook, dressing area, a full bathroom, and a 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. Permit# 0234. Offered Apr $11,000; May $20,000; June $25,000; Sept 5-30 $25,000; Oct $20,000; Nov $15,000.

A light, bright and mint condition Orient Village 4 bedroom, 4 bath bayfront home, featuring beautiful classic lines and architectural details throughout. Walls of windows and high ceilings showcase stunning sunsets over Orient Harbor and beyond. Gourmet kitchen, open floor plan with glass doors to outdoor dining area, waterside lawn, two decks and stairs to the water makes this a perfect opportunity for entertaining and family relaxation. Rental includes a gas grill, 2 boat moorings and nearby association sandy beach. This very well appointed home includes an open fireplace, perfect for an extended stay throughout the fall and beyond in an idyllic location that beckons peace and relaxation surrounded by nature and luxury. Nov-March $12,000/mo.; Apr $14,000; May $16,000; June $25,000; July $40,000; Aug $60,000; Sept $60,000. Permit# 0595.

7 WEEKS OF BLISS!! THINKING OF RENTING A CHARMING HOUSE IN MADISON FOR THE SUMMER? Available from June 30, 2024 to August 18, 2024. The Landlords are seeking a renter to take the entire term (no weekly or 2 week rentals available). Called The Wendell Farm, this 3 bedroom home has a chef's kitchen, hardwood floors, open floor plan, and newly added Master Suite in 2008. Spectacular Madison Beaches are a 5 minute drive away. Downtown Madison is 3 minutes away. The public middle school across the street, Polson Middle School, has tennis courts and playing fields. Complete with the quintessential red barn, the barn is home to a few horses and chickens (fresh eggs!). Come experience the easy summer lifestyle in Madison. (Horses are boarded and owners by others, the chickens are the Landlords, but can visit another family for the summer if Tenants prefer no chickens). Landlords and house are pet friendly. Tenant pays for electricity.

Bayfront beach Cottage with panoramic views, stylish & chic. Great room with newly renovated kitchen, dining area, living room, bay side deck. Master bedroom & bath and additional guest bedroom & full bath, outdoor shower, private beach. Offered Nov 2023-March 2024 $4,000/mo.; 2024: Apr $4,500; July $14,000, Aug $16,000, Aug-LD $17,000; Sept $9,000; Oct $5,000. Permit# 0569.

2024 Rates: June $6,250/week or $25K/month; July $8,125/week or $32,500/month A1-LD $8,750/week or $35K/month. Experience North Fork summer living in this newly introduced gem! Nestled in the sought-after Eastern Sterling Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach. 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.

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

2025 Rates: MDW-LD $142,500; June $30K; July $52,500; A1-LD $55K. This Modern Hamptons style home offers everything you could ask for from a Summer retreat to the East End. Featuring over 3500sqft of living space, the impressive Great Room is the centerpiece of the house and flows seamlessly to the rear yard which features a 20x40 heated gunite pool with sun deck, large architectural stone patio w/ fire-pit and large gas fired grill. In addition, you will enjoy lazy summer walks to the Rock Cove Estate community private Sound side beach and peak-a-boo water-views from the second floor. All bedrooms are generously proportioned but the Primary En-Suite is truly spectacular with high vaulted ceilings, private waterside balcony, walk in closet and En-suite full bathroom. Bonus feature, the second floor offers a game/media-room w/ full-size pool table, shuffle board table and waterside balcony. Don't let this amazing offering slip away!

Spend your summer enjoying all the North Fork has to offer at this Greenport waterfront home with dock and community bay beach. Completely updated with high end touches throughout including chef's custom kitchen with island, 3 bedrooms (2 are en-suite), 4 full bathrooms, expansive waterfront deck, and a lower level entertainment lounge. The perfect place to relax and unwind.

July is now gone, AVAILABLE ONLY in AUGUST this quintessential Seasonal Beach Cottage with WATER VIEWS is special The views out over Long Island Sound AND a wonderful wraparound South facing Open Porch to catch the summer breezes are both part of this charming Cottage, located directly across from the very desirable Overshores (SANDY) Beach Association with it's large grass play area, boardwalk, gazebo & even a raft!, Besides the water views from every room, a light & bright open floor plan, high ceilings, a small but cool sleeping porch/room, new ceiling fans, updated Bathrooms, full size washer & dryer and an outside hot/cold shower, the Kitchen has granite counters, stainless appliances including a dishwasher & a butler's pantry. MINIMUM OF TWO WEEKS & may be extended into Sept/Oct at a lesser rate. OFF SEASON in May & June possible too! Sleeps 9.

AVAILABLE FOR MONTH OF JULY. Relax and unwind for a summer at the beach. This well maintained, freshly painted three bedroom home with vintage beach house charm has easy access to a private Association beach just steps away. Three carpeted bedrooms are: one king (master), one full and one with 2 twin beds. This home has an L shaped Living Room and Dining Room. The kitchen is well equipped for all of your food preparation needs. Ductless AC on 1st floor and in each bedroom. A wonderful, expansive front porch with screens is a great place to entertain or read. The back and side yards are perfect for all types of summer games and provide a clear view down to the water! The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison. Some pets considered.

AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, freshly painted three bedroom home with vintage beach house charm has easy access to a private Association beach just steps away. Three carpeted bedrooms are: one king (master), one full and one with 2 twin beds. This home has an L shaped Living Room and Dining Room. The kitchen is well equipped for all of your food preparation needs. Ductless AC on 1st floor and in each bedroom. A wonderful, expansive front porch with screens is a great place to entertain or read. The back and side yards are perfect for all types of summer games and provide a clear view down to the water! The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison. Some pets considered.

Square footage is approximate as Town of Southold does not have square footage of second half story recorded.

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

Experience serenity at this stylishly renovated and tastefully adorned cape in the heart of Greenport village. This expansive residence offers three bedrooms, including a master suite with a private bath, two additional bathrooms, and a convenient home office. The main floor embraces an open-concept design, featuring light-filled dining and living areas, along with a well-appointed kitchen boasting stainless steel appliances. The fenced-in yard creates a tranquil space for stargazing after a day of summer adventures. Just steps away from Greenport Village's restaurants, shops, the Shelter Island Ferry, train, and Jitney bus, and a short distance to popular 67 Steps Beach, this is the perfect location for your unforgettable Greenport summer getaway.