Luxury properties for rent Osterville, United States

Exceptional rental opportunity on Menemsha Pond. This stunning compound features a main house with eight ensuite bedrooms, showcasing a remarkable first-floor primary suite with two full bathrooms. Two kitchens, equipped with top-of-the-line appliances, provide a luxurious culinary experience. Additional features include a home theater with massage chairs and expansive indoor and outdoor living spaces against the backdrop of breathtaking water views. Included with the main house is a large waterfront deck with outdoor Italian seating that can comfortably accommodate 20 people. There is an outdoor dining table that can accommodate 24 guests, as well as a large built in Kalamazoo grill and pizza oven, an outdoor wooden bar, an outdoor built in stone fire pit and two large built in Tucci umbrellas. The pool house serves as a haven of relaxation, featuring an indoor heated 10' X 30' pool and a spa surrounded by floor-to-ceiling sliding glass doors that seamlessly blend the interior with the exterior. Additional amenities include a sauna, steam room, wet bar, and two guest bedrooms. The second-floor is a full guest suite, including a large bedroom, washer and dryer, a living room and two spacious balconies.The first-floor guest bedroom enhances the overall luxurious accommodations. Perched atop the compound is a hilltop writer's cottage with one bedroom, offering panoramic views overlooking the pond. Also included on the property is an entertainment building including a large full gym with various cardio and weight machines by Technogym and Peloton. The gym features floor-to-ceiling windows providing scenic views. There is also an indoor basketball court with an NBA professional basketball shooting machine. Below is a 6 car garage with Porsche and Tesla electric car charging stations. Guests can also enjoy outdoor recreational activities with a tennis court that doubles as a pickle ball court with appropriate lines, and a large cedar jungle gym. The property includes a 115' deep-water dock with a boat house featuring numerous waterfront activities including paddle boards, kayaks, and wetsuits for added convenience. Additionally, three purpose-designed boats are available for use during the stay. Guests have the option to rent one, two, or all three: Boat One is a 55-foot Novamarine BS160, custom made in Italy, equipped with 5 outboard Mercury Racing engines and significant customization (captain required). Boat Two is a Mastercraft X26, perfect for water skiing, wake surfing, wakeboarding, etc. The boat features a computer touch panel for creating a customizable surf wave behind the boat. Boat Three is a Zodiac Open 7.0 speed boat, versatile for water skiing and well-suited for navigating open oceans with waves. This 26-foot boat is powered by a Yamaha 200 HorsePower outboard engine, offering both agility and stability on the water. The nearby beaches offer delightful opportunities for sunbathing, swimming, and savoring the picturesque ocean views. Menemsha, a charming fishing village nestled in Chilmark, is celebrated for its delightful harbor, delicious seafood, and enchanting sunsets. From the property itself, guests can enjoy breathtaking views of Menemsha Pond, particularly at sunset, when warm hues paint the sky and cast reflections on the serene waters, creating a tranquil and visually captivating setting. The island plays host to a variety of events and activities, including farmers' markets, art fairs, and community gatherings. The lush green surroundings, invigorating coastal breezes, and overall sense of serenity make it an attractive destination for those in search of an escape. This rental opportunity guarantees an immersive, high-end escape where guests can unwind in a serene atmosphere, surrounded by the beauty of nature and the thoughtful luxury woven into every aspect of the property. Available for any 4 consecutive weeks May-July & September-October

This stunning 3-bedroom rental embodies the epitome of seasonal living with its exquisite design and comfortable furnishings whether you are looking to stay in Newport for the summer or winter. Upon entering, you'll be greeted by a bright and airy living space adorned with tasteful decor and thoughtfully chosen furnishings that effortlessly blend style and comfort. There is central AC, a fireplace and off-street parking PLUS a quaint fenced-in yard. The second floor has two bedrooms: the primary where you can step outside onto your private balcony for a little quiet time and R&R and a guest room with two twins. A private bedroom suite is located on the third floor with its own bathroom. In case a little separation is needed, the basement is finished and offers a pull out couch and an TV room. Convenience is key during your stay, and this rental delivers just that. Whether it's proximity to the beach, local attractions, or vibrant dining spots, this property situates you within easy reach of all the seasonal delights the area has to offer. AVAILABLE FOR JUNE, JULY AND SEPTEMBER 2024 and OCTOBER 2024-MAY 2025. Please inquire about rates.

Available for August 2024. Charming newly renovated cottage available for summer rental. This cozy retreat features modern updates and a fresh, inviting atmosphere. The cottage boasts a nice layout with a spacious living area, a fully equipped kitchen, and three comfortable bedrooms and two full bathrooms. CENTRAL AIR, SECOND-FLOOR LAUNDRY and FOUR OFF-STREET PARKING SPACES. Enjoy the beautiful surroundings from the private deck or take a short walk to the nearby King's Park for beach access. Perfect for a relaxing summer getaway, this cottage offers a peaceful escape with all the amenities needed for a memorable vacation. Also available for June ($12k), July ($15K), and September ($12k).

Available for September 2024. Charming newly renovated cottage available for summer rental. This cozy retreat features modern updates and a fresh, inviting atmosphere. The cottage boasts a nice layout with a spacious living area, a fully equipped kitchen, and three comfortable bedrooms and two full bathrooms. CENTRAL AIR, SECOND-FLOOR LAUNDRY and FOUR OFF-STREET PARKING SPACES. Enjoy the beautiful surroundings from the private deck or take a short walk to the nearby King's Park for beach access. Perfect for a relaxing summer getaway, this cottage offers a peaceful escape with all the amenities needed for a memorable vacation. Also available for June ($12k), July ($15K), August ($15K).

Single level luxury living offered for September 2024 - May 2025. With character-rich details at every turn, this stylish abode has just undergone a spectacular resurrection. From the sun-drenched eat-in kitchen with double-height ceilings to a glamorous den adorned with an opulent creamy shell chandelier- this midcentury cottage offers delightful, carefully designed elements around each and every corner. The den flows into a light-filled, three-season room (which could serve as an office) overlooking the patio — the perfect sunny spot to read, rest or converse. Past the vibrant powder room is an alluring hallway with a glossy, edgy green ceiling leading to the “sleeping wing,” with four exquisitely appointed bedrooms and three full baths. The woodland-inspired primary suite boasts views of the European-inspired in-ground pool and an acre of lush grounds- perfectly fenced-in and landscaped. The lower level has been finished to create a hip lounge space with adjacent laundry room. With plenty of parking, plus a 2-car garage, this home is exactly what you have been waiting for.

Waterfront Summer Rental Opportunity in Jamestown Waterfront Summer Rental Opportunity in Jamestown A classic shingle-style home located on the waterfront of Jamestown Harbor, this beautiful home offers all of the amenities of a luxury summer experience. Tastefully appointed with a modern kitchen, beautiful baths, and a large wraparound porch, gorgeous sunrises and panoramic water views of Narragansett Bay, the Newport Bridge, Fort Adams, and Clingstone await. With 7 bedrooms in the main home and a 8th bedroom suite in the garage apartment, located just a short walk to Jamestown’s shops and restaurants, 30 Bay View Drive presents a singular opportunity. Available for off-season stays as well, please inquire Location · Waterfront · Mooring Available · Walk to Village Shops & Restaurants Property Amenities- · Central Air Conditioning · Linens Included · Gas Grill Recreational Items- · 4 Kayaks Sleeping Accommodations by Bedroom Level 1- · Bedroom 1- Queen Level 2- · Bedroom 2- King · Bedroom 3- Two Full Beds Level 3- · Bedroom 4- Queen · Bedroom 5- Twin · Bedroom 6- Two Twins Garage Apartment · Bedroom 7- Queen

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.

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.

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.

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.

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located to all forms of public transportation and close proximity to public Bay beach. This property offers convenience, style and stunning views of Shelter Island and the Peconic Bay. Main features are large front porch, inviting/well appointed living spaces multiple en-suite bedrooms and a large rear yard for entertaining. This historical treasure has been recently updated and provides both the charm of a classic New England port village home and the accommodations of an updated home. Easy North Fork living in Greenport Village.

Charming exquisitely restored mission style cottage with unique privacy. Original beach stone fireplace, custom woodwork throughout, large deck, screened porch, 2 ensuite bedrooms, studio / office, gourmet kitchen and period furnishings. Walk to 2 beautiful sound beaches. July $15,000; Aug $15,000; Aug-LD $17,000. Permit# 1003.

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.

Available for the month of July 2024. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the summer days and nights. Updated kitchen with stainless appliances and large dining nook, mud room and office and dedicated laundry room and half bath all found on the main level. Four levels of living make this the perfect home for multi generations: with a main level bedroom with Queen bed, Master Suite on the second level with en- suite bath and office nook with a private balcony, second bedroom with bunks -on the third level is the fourth bedroom with twin beds, shared full bath on the second level. Lower level has a rec/play room. Access to the Soundview Association beach.

Available August 1 through Labor Day $25k. Spend a perfect summer month in this Gorgeous Connecticut Antique Edson Bradley Estate, beautifully updated 3 bedroom antique home, with an additional 1 bedroom guest apartment in the nearby renovated barn, a gunite pool with views west, apple orchard and a lovely park-like setting. The 3 bedroom home main house offers open kitchen to Conservatory for great light and family along with living room and library. Just a short drive to Roxbury Center, and privately sited with a grove of pine trees. Close to Roxbury Land Trust's gorgeous hiking trails, the Shepaug River and Maple Bank Farm, and just minutes away from Washington Depot, New Milford and Woodbury for great shopping and restaurants!

Set in one of the most beautiful areas of Roxbury and short walk to acres of land trust, this light, bright and airy open floor plan 18th century Colonial has over 26 acres of peace and quiet. There is a large tranquil pond which is surrounded by white pine trees. A place to one with nature! The home features 2 primary bedrooms, one on each level and an additional bedroom on the second level. The designer kitchen with Carrara marble counters, a vaulted ceiling and custom island opens to a stone patio and screened porch. The huge living room is light filled with wide board floors, French doors and a wood burning fireplace. This home also features central air conditioning, a security system, first floor laundry. Enjoy the sites and sounds of nature in this very special retreat property and relax in this paradise, under 2 hours from New York City.

Spacious Beach House available for the summer months. In the heart of the beach area, 453 Birch welcomes you home with four to five bedrooms, updated kitchen, first floor full bath, private yard and spacious upper deck. The newer kitchen has granite counter tops and gas stove. Nearby is a living room for all to gather. Upstairs there are four spacious bedrooms, all with great closet space, and the second full bathroom. Outside you'll find a large deck, and peaceful and private yard. Shady trees, blooming bushes and fragrant flowers provide a serene getaway, right in your backyard! This home is nestled perfectly between downtown Fairfield and Penfield Beach on one of the most desirable streets in the beach area. A short distance to the beach, parks, playgrounds, schools, downtown, the library, restaurants, the train station, and more.

Available Jan through March at $12.5k per month. April - $15k, May - $20k. This historic Victorian home in the New Preston section of Washington is now available for rent after being tastefully renovated from top to bottom. The main level 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 40x18 heated saltwater pool features an electric cover and 8 person attached hot tub. This home is just a short stroll to swimming and boating at Lake Waramaug, shopping in the New Preston town center, 30 minutes to skiing at Mohawk Mtn. & Metro North trains, and 90 minutes from Manhattan!

Lee Colonial with 4 bedrooms, 2.5 baths short distance to town of Lee and Lenox. Open kitchen dining, living room with fireplace that connects to a sunroom. Upstairs is the primary bedroom with new bath with shower and 3 guest bedrooms that share a full bath with shower/tub combo. Renovated great room with built ins right off the garage. Laundry in basement. Deck overlooking the large backyard. No pets. Plus utilities. Central a/c. Available end of August 2023 to June 1st 2024

Charming and bright guest cottage with beautiful distant views of Lake Waramaug in a park-like setting with a lovely stone patio, and separate driveway and parking. The main level of the cottage, which has charming painted floors and wooden beams, consists of an inviting open living room/dining room conducive to entertaining or cozy evenings spent on the couch, a galley kitchen and a powder room. The second floor has a large open hallway with built in bookcases running the entire length of the hall. The primary bedroom offers a cathedral ceiling and a beautiful view of the lake. The second bedroom, also with a view of the lake, has matching twin beds, while the third bedroom is currently set up as an office, making this a perfect work-from-home spot to snuggle into for the winter. This house is in a wonderful spot for long walks while admiring the beautiful views of the Lake. It's very conveniently located near Hopkins Vineyard, Hopkins Inn, the Warren Town Beach, and The Owl restaurant. It is also just minutes to the sought-after shops of downtown New Preston, 20 minutes to Mohawk Mountain Ski Area, and 30 minutes to the train station. The house is available immediately and can be rented through the end of May or mid-June. Alternatively, it is available as an annual lease, however, the rent for each of June, July and August would be $5,000 per month ($3,800 all other months). Private use of the pool may be used by the tenants on a scheduled basis with the landlord.