On the Market: 9 Rentals for Your Best Summer Yet

With spring officially here, summer is just around the corner. And what better way to celebrate the beautiful, warm weather ahead than finding your next home for more than a weekend getaway. These rentals are available on a weekly or monthly basis and are found all across our hottest summer markets—from Martha’s Vineyard to the Hamptons.

Martha’s Vineyard, Massachusetts

18 Sprice Gate Road in Chilmark, MA | $25k/month | Agents: DJ Gendreau and Allison Parry

Squibnocket Farm: double-gated, 6 Acre, 4 bed, 3 full bath, with powder room. Breathtaking ocean and meadow views from every room. Deeded access to the most prestigious beach on Martha’s Vineyard. Vaulted ceilings, cherry flooring, exposed wooden beams with professionally appointed furnishings throughout. Gourmet kitchen with Viking and Sub-Zero appliances. Open concept: Living and Dining rooms, complemented with a Yamaha grand piano. Family room with comfortable seating and working fireplace. Enjoy outdoor living atop teak furniture on the large deck and patio, covered screened porch with fireplace. Smart home features, with Ubiquiti Network offering continuous connectivity. Surrounded by 300 acres of conservation land; providing supreme privacy. Scottish Cheviot sheep pastured nearby. Listing price reflects weekly rate during the 2021 summer season. Call for availability.

16 Allen Farm Road in Chilmark, MA | $10-20k/week | Agent: Jesse Greenstein

WEEKLY RENTAL $10,000-$20,000 per WEEK. Built in 2018, the exquisite post & beam Allen Farm Hilltop Farmhouse perched 150 feet above Lucy Vincent Beach & the Atlantic Ocean in Chilmark has the best views on the island. You will not be able to beat the location or the experience renting a property like this provides you and the family. The 100+ acre property is surrounded by stone walls and the natural beauty of up-island MV. House has direct access to Lucy Vincent Beach & Chilmark Pond. Enjoy the fresh veggie garden & eggs provided by the farm, as well as the beautiful & historic farmland & pastures that have been owned by the Allen family since 1762! The 3 season screened in porch, chef’s kitchen, and open layout are ideal for entertaining. Sleeps 10. 3+ bedrooms, 3 full bathrooms, + outdoor shower. The rental comes w kayaks/canoes, and views as far as the eye can see. Linens provided. +9.7% rental tax +$800 cleaning fee.

421 S Road in Chilmark, MA | $10-20k/week | Agent: Jesse Greenstein

WEEKLY RENTAL $10,000-$20,000/WEEK. Fully updated in 1998 1773 Allen Farm Farmhouse perched above Lucy Vincent Beach in Chilmark is one of the greatest properties Martha’s Vineyard & New England. If you know about Allen Farm, then you already know how special this place is, & how rare it is to be able to call this property home. Home sleeps 10, has 5 bedrooms, 3 bathrooms, a jacuzzi, open concept chef’s kitchen & dining room w two living rooms, screened in porch, outdoor shower, & master bed on main floor, 3 bedrooms on the 2nd floor & big bedroom w 3 beds on the 3rd floor. The property is surrounded by stone walls, & offers direct access to Lucy Vincent Beach, Chilmark Pond & pasture in the front yard, & farmland/pasture in your backyard w fresh organic veggie garden at your disposal, you simply will not find a better vacation home. Comes w Kayaks/Canoes. +9.7% rental tax +$800 cleaning fee


33 Rippowam Road in New Canaan, CT | $20k/month | Agent: Monica Webster

Pass the long sweeping private driveway to a serene, private oasis of natural beauty plus tennis court. Captivating views of 2 plus acres of both kayaking pond and pool provide blue from every window,as you enter this bright modern five-bedroom cosmopolitan home. Celebrity builder Meadowbrook Contracting Inc. showcases all-custom finishes, stone fireplaces, unique millwork and high ceilings. Flowing and creative interiors tailor-made for creating memories with family and friends. The spacious hall opens to a beautifully scaled living room with fireplace and wet bar. The formal dining room has an elegant 9-foot high coffered ceiling. Exaggerated ceiling enhance both the family room and an up-to-the minute modern luxury kitchen: offering top custom cabinetry, a large center island,Quartz countertops, stainless appliances plus a convenient wine tower. Expansive terrace,a blue pool and lush private yard surrounding the tennis court afford wonderful outdoor living spaces off a main floor. Two gorgeous master options with a first floor bedroom featuring a fireplace, walk-in closet and spa bath with tub, shower and heated marble floor. Two staircases connect with four more en suite bedrooms and the upper floor balcony and sitting room brings in stunning water views.


158 Westwood Drive in Bedford, NY | $25k/month | Agent: Sally Slater

Beautifully appointed home in an estate area- private and quiet with an in-ground salt water pool. Attention to detail throughout. Available from May thru September or part of this time . Stable is not available with this rental.Owner pays for groundskeeping and opening pool. Sonos sound system and outdoor furniture included.


271 Dune Road, Bridgehampton, NY – Monthly: $375,000 | Agents: Paul Brennan and Martha Gundersen

This world class estate on iconic Dune Road in Bridgehampton is sited on approximately three of the most coveted acres on the East End, offering permanently protected and unobstructed panoramic views of both the Atlantic Ocean and Mecox Bay. Enjoy unparalleled privacy far from public beaches or parking. The property features 275 +/- FT of frontage and includes deeded bay access. This deeded access allows for water sports and outdoor entertainment of every variety from jet skis and paddle boards to motor boats. This newly renovated classic is an 8,000 SF state-of-the-art residence featuring 8 bedrooms, 6 with en-suite baths, 2 smaller bedrooms sharing a full bathroom, 2 additional half baths, and an outdoor shower. The entire property is equipped with top-of-the-line electronics and security with high-speed internet indoors and out. There is a Control 4 entertainment system as well as motorized shades in all rooms. This elegant property, designed to take advantage of its preeminent location, boasts postcard worthy views from nearly every room as well as an oceanside sundeck and dining area. French doors open to the newly installed bluestone patio with an al fresco dining area adjacent to a new 52′ x 18′ heated gunite pool with separate spa. Additionally, there is a second story Ipe deck ideal for lounging while overlooking a white sand ocean beach. The spacious master suite has access to this deck as well as an additional private covered deck off the spa-like master bath. The grounds are complete with a lush rolling lawn, three separate parking areas, and both a primary and service driveway. The home’s interiors are grand and detailed with an abundance of natural sunlight. The gracious billiard room leads to the adjacent den with home theater and wet bar. A separate private office offers extraordinary bay views. The large country kitchen is equipped with every modern amenity including a six burner gas range, two farm-style sinks, double ovens, double Miele dishwashers, commercial Sub Zero refrigerator as well as dual Sub Zero wine refrigerators and a marble fireplace. On either side of the kitchen one will find a spacious family room and elegant dining room. The living room with wood-burning fireplace enjoys fabulous views. A true oasis, this estate offers unmatched privacy.

7 Pine Tree Lane, Westhampton, NY | Memorial Day – Labor Day: $360,000 | Agents: Regina Cigna, Linda Haugevik

Newly listed, offering 182 +/- feet of waterfront, including 140 +/- feet bulkhead, and 150 +/- foot deep water dock. This four bedroom, four and one-half bath home comes with its own private sandy beach, heated gunite pool, separate spa, expansive lawn, har-tru tennis court, and hardwood decking in a secluded setting with Western sunsets. Chef’s kitchen, garage, are just a few of the many features. Located within close proximity to Westhampton Beach Village shopping and restaurants and Dune Road beaches, this home has it all!

154 Captain’s Neck Lane, Southampton, NY | Memorial Day – Labor Day: $375,000 | Agent: Lynda Packard

Nestled on almost 2 acres in the Estate section of Southampton Village, this beautifully decorated designer home boasts five large bedrooms most with en suite baths plus two lower level bedrooms for extra accommodation, formal living and dining rooms, a den/lounge, eat-in kitchen, an all-weather surface tennis court and a gunite pool with well-equipped poolhouse including a full bathroom, wet bar, living room and outside patio. Enjoy the summer in the perfect setting and listen to your music on the newly installed Sonos system.

65 Herrick Rd, Southampton Village, NY | Memorial Day – Labor Day: $450,000 | Agent: Paula Hathaway

This three-story, eight-bedroom, seven-bath home is in mint condition–just restored to the glory of the early 20th century, right in the heart of historical Southampton Village! If you love open and simply elegant living this home is perfect for your summer enjoyment. The immaculate renovation revives the character of the earliest village homes.There is a pool house with a bath and outdoor shower attached to the two-car garage in the pool area. The large open veranda off the back of the house overlooks the rolling lawns of this picture-perfect vacation home. Just under a block to Main Street and under a mile to the wide, sandy Atlantic Ocean beaches, this property is one to consider for summer 2021. No pets allowed here. Available now for the full summer.

Find your next summer rental today.

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