luxury houses for rent Old Saybrook, United States

Find your tranquil summer retreat in a prime location, at this immaculate contemporary waterfront home set on 1.5 private acres in irresistibly charming Essex. Available June and September at $15,000 per month, and July and August at $20,000 per month. Multiple balconies and bluestone terraces (including one at water's edge) make this the perfect place to relax, unwind, and enjoy cool river breezes on a sunny Essex summer day. Step inside to a vaulted open interior filled with natural light and sophisticated ambiance. Prepare meals in a modern kitchen equipped with Wolf and Subzero appliances. Dining and living areas flow seamlessly. Two bedrooms with ensuite baths, a powder room, and laundry room, are located on the main level. The primary suite features a vaulted ceiling, floor to ceiling windows, an ensuite bath, and an adjoining room that can serve purposes from office, to yoga space, to nursery! The ground-level floor plan is equally open and offers a spacious family room, both a full bath and powder room, guest bedroom, and access to the three-car garage. A detached barn is where you will find kayaks and a golf cart for your use to zip down to the sandy riverfront beach, Adirondack chairs on the riverside terrace, and a private dock on the water. Discover all Essex village has to offer, minutes away. Historic landmarks, charming boutiques, waterfront eateries, yacht clubs, and the CT River Museum. Make this summer one to remember! Just over two hours to NYC or Boston.

This rental is available 6/1/2024

Come spend fall, winter and spring in the heart of Middle Beach! Fabulous direct water front Academic Rental available September 15th through May 15th 2025. Main level with open concept and stunning waterviews has gas fireplace, updated kitchen, dry bar and the first of three full baths. Second living level offers 4 bedrooms and two full baths; comfortably sleep six. The primary bedroom has stunning views, walk in closet and full bath with stall shower and double sinks. A third floor with deck and office nook is the perfect spot to watch the sunsets. Some pets may be considered- no cats.

ACADEMIC RENTAL - Fabulous location..Walk to downtown Madison or East Wharf Beach. Four bedroom home with a 1st floor master bedroom with king sized bed and access to the outdoor shower. Large and bright family room with a wood burning fireplace opens to the 3 season porch and stone patio. A second bedroom with twin bunks is on the first level as well as a full bath. Second level offers two additional bedrooms (full bed and two twins) and another full bath. Available Sept 7th 2024- June 14th 2025. Some dogs maybe considered- no cats.

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15,000; Aug $15,000; Sept $8,000; year-round, furnished starting Sept $32,000/mo. Permit #0308.

Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite bedroom, additional full bath, Malm fire drum, & infra-red sauna. The main floor offers an open floor plan with living/dining/den/kitchen, a 2-sided fireplace, new kitchen, new baths, waterside & farm view decks. A professional ping-pong table, CAC, & outdoor shower are additional amenities. The panoramic Sound and farm views on 1.84 acres offer unique privacy. Offered July 65,000; Aug 75,000. Permit# 1059.

Stunning Waterfront shingle style home overlooking Long Island Sound. 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 Aug-LD $55,000; Sept 5-30 $25,000. Permit# 1108.

Beautifully converted 19th C Barn - three story residence with 4 bedrooms, 3 full baths, Eat-in kitchen, deck off living room with sound views, and private beach access. Apr $5,000; May $5,000; June $8,000; July $15,000; Aug $15,000; Sept $10,000; Oct - Mar $4,000/mo; yearly $6,500/mo. Permit# 0774.

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished basement with projection TV. Available October, November, and December for 2-week minimum period for $3,000 per week. Permit #0441.

Experience the ultimate North Fork summer with the perfect combination of comfort and privacy in this spacious 4 bedroom home with heated pool on 3.5 acres. Explore the pristine beaches, beautiful vineyards and breweries or check out one of the many chef renowned restaurants the area has to offer. This property is the ideal retreat for a memorable summer getaway on the North Fork.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered July $10,000; Aug $10,000; Sept $7,000. Permit #0091.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; May $10,000; June $16,000; July $25,000; Sept $16,000. Permit #0827.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; Aug 12-26 $10,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

Summer in Orient. Relax on the front porch of this 3 bedroom, 2 bath Ranch in Green Acres, a short walk to association Sound beach & Orient State Park. Open floor plan with updated kitchen, wood burning fireplace & rear deck off dining area - perfect for entertaining. Private yard with specimen trees & vegetable garden with automatic sprinkler system. Available June $5,000; July $8,000; August $9,000; September $4,000; MD-LD $22,000. Permit # 0208

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