Vacation Rentals By Owner In Shelter Island, NY

$480.52

Charming secluded island cottage

Shelter Island, New York, United States

Charming secluded vintage cottage surrounded by nature preserve on 1/2 an acre yet centrally located mid-island. Fully furnished and equipped with everything you need, from beach chairs, towels and umbrella down to an immersion blender.brbrDepending on the day and week, I can often be flexible with check in and check out times. Please feel free to reach out with any questions regarding stays. Shelter Island has passed a no short term rental law which I am happy to answer any questions about.brbrMy home on Shelter Island is my happy place. I spend time here year round, and because of this, it is pretty well stocked from to spices to band aids. It is not like staying in a standard rental that is used only for guests. There are plenty of books, WiFi, but no television. br brThe house is down a dirt road, and surrounded by nature preserve (and a lot of bamboo.) It is mid island between the North and South ferries, and 2 miles to either Wades or Hay beach. The nearest (deserted) beach/water is Coecles Harbor, half mile away, accessible down the back road.brbrThe house is small but open. On the first floor there is a bedroom with a queen bed, and a porch/sunroom with a single bed set up as a couch. There are two sleeping lofts with skylights upstairs accessible by a hand hewn spiral staircase made from a telephone pole. One has two twin beds, the other a queen bed. The space is a converted attic, so think low slanting ceilings. brbrI upgrade the house as I go along, there may be small changes in the photos like new lamps, or pillows. brbrThe outdoor space has a deck with a grill, a table that will seat 4-6 and, and a small seating area. There is also a hammock and a rustic outdoor shower.brbrThe kitchen is a bit retro, but pretty well equipped, with a brand new new air fry convection oven, microwave and toaster oven, Keurig coffee maker, blender, mini food processor, immersion blender, pots and pans, etc...I just put down a new floor, and upgraded the cookware and knives. brbrThere is a washer and dryer off of the kitchen. brbrThe house can sleep 5, but because of the size is probably more suitable for 2-4 people. brbrbrThe bathroom downstairs has a tub and shower, as well as towels and toiletries. There is a very basic half bath upstairs, handy in the middle of the night :)brbrThere are beach chairs, an umbrella, and an assortment of beach towels and basic canvas beach bag on the porch as you enter the house.brbrAround the corner where Shelter Island Kayak rents their boats, I have one kayak that is available to use anytime. I'm working on getting another one. brbrPlease reach out with any questions!

Bed

Bath

Sleeps

$1626.7

/ Nightly

Private Vacation Home

Contemporary Home with heated pool and waterviews on Shelter Island

Shelter Island, New York, United States

Our Shelter Island beach house is within a 5-minute walk to beautiful Wades Beach. A heated salt water pool is located within an enclosed patio and has an automatic safety cover which can only be accessed by tenant with a key (lock is separate from the pool), providing peace of mind to anyone with small children or guests.brbrEnjoy close proximity to one of Shelter Island's beautiful beaches and relax in the pastoral yard while grilling your dinner.brbrIt offers guests a peaceful and quiet spot for an unforgettable vacation only 100 miles from New York City. Our beach house is situated on more than one acre on South Midway Road, about 1 mile from Shelter Island Heights, with easy access to the surrounding restaurants, shops and Mashomack Nature Preserve. Our house is just a short walk from the house to the sand and the water. brbrThe interior features 4 bedrooms (2 master bedrooms with private bathrooms) and 3 full bathrooms in a sunny two-story-style layout (dual zone Central Air equipped). Beautiful Vintage doors and classic appointments adorn the open floor plan with beamed ceilings, cast iron tub, country kitchen and stained glass windows. The master bedroom has a veranda to enjoy.brbrThe backyard has a wraparound porch with furniture, sunning deck and gas grill perfect for a barbecue. The large backyard is ideal for summer evening entertaining. Comfortably furnished, our house provides a relaxed atmosphere in wonderful surroundings. It is close to local restaurants, boat yard, ferries and all amenities that Shelter Island offers.brbrPlease note: I do not allow pets of any kind. brbrHouse features: br18 x 36 heated salt water poolbr4 large bedrooms (1 king, 1 queen, 1 full and 2 twin)br3 full bathrooms brSun room brLiving room brPrivate upstairs deck brLarge backyard (1.25 acre) brFree Highspeed Wireless Internet Network brCentral A/C & Heat throughout brCeiling fans throughout brTwo televisionsbrDishwasher brMicrowave & Oven brGas GrillbrLaundry room with washing machine & dryer

4

Bed

3

Bath

8

Sleeps

$4312.94

/ Nightly

Private Vacation Home

Congdon's Point Shelter Island

Shelter Island, New York, United States

Please contact us for availability. brbrCongdon`s Point is a five bedroom, six and one-half bathroom private home that is surrounded by water, beach and nature preserve.brbrEach bedroom features en suite bath with steam shower and Aesop amenities.brbrThe kitchen, complete with exposed hardwood beams and handcrafted finishes, features a Thermador Professional series oven, and is fully equipped with enough equipment, appliances, small wares, and service pieces for just about any cooking or entertaining need.brbrThe living room features 24` high ceilings, 10-foot-tall windows, and french doors leading to outdoor living spaces.brbrOutdoor living spaces include an immense wraparound veranda with numerous seating areas, an outside dining table and gas grill, a screened-in patio overlooking the gunite pool and hot tub sauna, and a waterfront lawn leading to the private beach and 100` dock.brbrThe Boat Barn houses a billiards table, dart board, and a bar.brbrMain House and Boat Barn brbrFive bedrooms, six and one-half bathroomsbrbrOne king master suite with tub and steam showerbrbrThree king junior master suites with steam showerbrbrOne trundle loft with two full size beds, one single trundle bed, bath and steam showerbrbrGunite swimming pool with hot sauna areabrbrPrivate beach with fire pit seating area and 100` boat dockbrbrProfessional kitchen outfitted for cooking and entertainingbrbrWrap-around veranda with screened-in sitting patiobrbrTwo-story living room with fireplace and formal dining roombrbrWiFi and whole home automation controlbrbrAesop bath amenitiesbrbrBilliards table, dart board and other gamesbrbrLandscape maintenance and pool service includedbrbrHousekeeping, electricity and gas deducted from utilities depositbrbrCurated Concierge and Dock Steward services available for additional feebrbrPool and hot tub closed after the October holiday weekendbrbr2021-L-96brNOISEbrNo parties or noise pollution are permitted. This is a quiet, residential area, not a resort. Quiet time starts at 9:00pm EST. Noise regulations are aimed to protect a rural, nostalgic way of life. If we are required to intervene in this regard, or if police intervention is required, all occupants will have to vacate the premises immediately and the guest will lose the entire payment and security deposit.brbrGUEST PERMISSIONbrIf the number of people on the premises exceeds the number initially indicated in the reservation, all occupants will have to vacate the premises immediately and the guest will lose the entire payment and security deposit.brbrPARKINGbrParking is available within the designated property parking areas – in front of the pool gate, and off to the side of the driveway entrance. Please ensure the long drive is always unobstructed.brbrPETSbrPlease note that pets or dogs are not permitted. There may be exceptions with service animals, for example. Please inquire, written approval must be provided in advance. An additional deposit and/or cleaning fee may apply.brbrNO SMOKINGbrThis is a smoke-free and tobacco-free property. Nowhere inside or outside is smoking, tobacco, vaping, or any inhaled substance permitted. If guest(s) do not follow this rule, all occupants will have to vacate the premises immediately and the guest will lose the entire payment and security deposit.brbrSHOES INSIDE THE HOMEbrAll guests should remove shoes before entering the home.brbrDOORS, WINDOWS, LOCKSbrPlease lock all doors and windows before leaving the property, especially doors and windows that will blow open if not engaged or locked. Guest(s) shall not change or re-key any locks or lock hardware.brbrLIGHTS, HVACbrPlease turn off all lights, inside and outside, upon departure. Please return the heat or air conditioning to 70 degrees Fahrenheit upon departure.brbrGARBAGE/REFUSEbrGarbage drawers are located 1.) to the left of the kitchen sink, 2.) to the right of the island sink, and 3.) the Boat Barn bar. All refuse and recyclables can be combined in the same receptacle – the town separates this. Once the garbage is full, please remove and tie the bag liner, then immediately drop into the large garbage cans on the far outside wall of the Boat Barn. Please do not leave garbage bags sitting on the floor inside the home, or the ground outside the home.brbrACCESS TO PROPERTYbrIf there are any legitimate reasons for concern (including, but not limited to, an electrical or plumbing problem, the presence of one or more animals, the use of tobacco or any other substance inhaled on the premises, over capacity, a complaint from the neighborhood, excessive noise or any other serious situation), a member of our team could enter the property and premises, without the prior consent of the guest, to ensure the integrity of the premises.brbrNATUREbrThe property is surrounded by nature, water, and wildlife. You may see deer, turkey, fox, squirrels, racoons, turtles, gulls and other birds, flying insects, butterflies, bugs, etc. While we have implemented property management protocols for a country setting, there are obviously aspects of nature and wildlife that are out of our control. We ask that you please clean up after yourself -- pick up all foods, drinks, empty food or drink vessels, and please keep trash only in the appropriate containers, inside or outside the home.brbrCLEANLINESSbrIt is the guest`s responsibility to keep the premises clean and tidy. The guest must, if necessary, wash the dishes they have used themselves, return everything to its original location, collect and take out their garbage, etc. If the property is left untidy at the end of the rental period, a fee for each additional hour of cleaning required beyond the included cleaning will be deducted from the security deposit.brbrINVENTORYbrThe inventory is established before arrival and after departure. A critical walkthrough of the property after departure allows us to assess the condition of the property per the rentals terms herein. Guest(s) must leave the premises in perfect condition, all contents, inventory and assets in perfect condition, and fully functional. The cost of any damage to the property and its contents, inventory and assets will be charged to you. If anything that presents a hazard that could cause damage to the apartment or to any person, guest(s) must notify us immediately.brbrHOUSEKEEPINGbrWe are happy to assist with special or additional cleaning requests. If there is an accidental spill, let us know immediately and we will assist. Please do not spray cleaning products on furniture or upholstered items. Failure to allow housekeeping employees to begin work at the pre-determined departure time will result in guests being charged a fee of $175 per hour. These hourly charges double 2 hours after scheduled departure/check-out time and are applied at the start of each subsequent hour. They do not apply if our team has previously authorized a late checkout.brbrHOLDOVERbrGuest(s) acknowledges and agrees that they are taking possession of the property for the agreed time period, and that it is important they vacate at the agreed upon departure/check-out time. As such, guest(s) agrees that should they hold over for any reason, or for no reason, and fail to vacate the property as agreed upon, that Host damages may be impossible to calculate. As Liquidated Damages, the guest(s) may be subject to pay an amount of $4,000 per day for every day the tenant holds over after departure/check out day.brbrFURNITURE, SMALL APPLIANCESbrBeds, sofas, tables, appliances, etc. should not be moved around. If you require assistance, please ask. Please do not operate small appliances such as space heaters or dehumidifiers.brbrPOOL, HOT TUBbrPool towels are in the cabinet of the common bathroom downstairs. Temperature can be controlled on the outside keypad next to the spa. Children must always be supervised around the pool and the hot tub. When finished with wet pool towels, please do not leave wet or damp towels on the floors of the house or on furniture. Please use the laundry baskets provided, or the drying rack.brbrGRILLbrThere is a gas valve behind the grill on the veranda to open and close gas flow. Please make all grill knobs are turned off and the gas valve behind the grill is returned to “closed” position after you’ve finished using it – “closed” position means the valve is perpendicular to the gas line and exterior house wall itself.brbrFIRE PITbrEnjoy. There are grey wool Pendleton blankets on the upper shelf in the mud room.brbrBATHROOMSbrShowers are glass enclosed, step-in shower stalls with hot steam settings. Activate the steam system by pressing the power, set desired steam temperature, and wait for the steam system to start (this can typically take a few minutes.) Please keep all hands and feet away from the steam hardware for your safety. There are extraction fans, lights and/or speakers above each shower. The Lutron switch closest to the bathroom entrance will provide control. Please turn off fans when shower is not in use. Please note that only toilet paper should go into the toilet due to the sensitive septic and ecosystem – no wipes or paper towels, for example, please.brbrWASHER, DRYERbrThe washer and dryer are in the basement. Laundry detergent and dryer sheets are provided. Please leave the washing machine door slightly ajar when finished.brbrTABLETOP, COOKWAREbrThere is formal dishware and glassware, and there is shatterproof dishware and glassware. Please use shatterproof dishware and glassware when serving food and beverage outdoors or poolside for your safety. There is no food or drink permitted in or around the bedrooms.brbrCOOKWARE, DISHWASHERbrThe two dishwashing machines on either side of the kitchen sink are for dishes, cups, glassware and flatware. Please do not machine wash pots, pans and other cookware. Dishwasher tablets are located under the kitchen sink.brbrBEACHbrThere is a path and bridge to the beach.brbrDELIVERIESbrIf you require special handling for any deliveries, please contact us in advance to arrange.brbrLIABILITYbrGuests

Bed

Bath

Sleeps

$448.88

/ Nightly

Private Vacation Home

Fishermans Cottage near Crescent Beach

Shelter Island, New York, United States

This 1920's original is nestled in a land reserve just off Crescent Beach. Enchanting and quiet, this property is in a unique position of having tranquil nature a short stroll from Pridwin, Sunset Beach...

Bed

Bath

Sleeps

$1271.03

/ Nightly

Private Vacation Home

Private oasis with new baths and heated Gunite pool near Wades Beach

Shelter Island, New York, United States

Fabulous open floor plan features soaring ceilings and a striking stone fireplace, as well as a gourmet fully equipped kitchen for the discerning cook. This 4 bedroom/3.5 bath beautiful home is private, nestled among mature trees and set far back from the road. The backyard is a secluded oasis with heated pool, chaise lounges, and an enormous NEW deck with a large teak dining table and seating for 10, comfortable lounging/seating area, and gas grill. All baths are newly renovated. On the front porch are comfortable rockers and vintage chairs, where you can enjoy your morning coffee or a glass of wine in the evening. Stargaze from your perch on the beautiful new deck outside the master bedroom. The first floor of the house has an expansive layout with open living and dining areas and kitchen with a breakfast bar, Subzero refrigerator and Wolf 6-burner range. A cozy family room, fully equipped with games and TV, leads out to the deck. A guest room (Queen) with ensuite bath completes the first floor. The second floor, includes a loft area (with twin sleeper and queen sleeper) overlooking the living area, a spacious primary (king) bedroom with ensuite bath and private deck as well as two additional bedrooms (one with king, one with twins and trundle) and a full hall bathroom with a new washer/dryer. Congdon's Creek is within walking distance and Wades Beach is just over a mile away. brbrTHE POOL IS NOT OPEN UNTIL LATE MAY AND CLOSES MID-SEPTEMBER UNLESS OTHER ARRANGEMENTS ARE MADE FOR AN ADDITIONAL FEE.brbrPLEASE ALSO KNOW THAT NO PETS OF ANY SIZE ARE ALLOWED AND THAT MINIMUM AGE OF PRIMARY RENTER MUST BE 30.

Bed

Bath

Sleeps

$2885.17

/ Nightly

Private Vacation Home

This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!

Shelter Island, New York, United States

This luxury home includes 6 bedrooms with additional sleeping accomodations for 4 in the downstairs walkout recreational room. All bedrooms have ensuite baths, 300 count linens & mutiple pillows & plush towels. The gourmet kitchen is a cook's dream. With water views from all areas of the home, this house lends itself to outdoor dining as well as warm summer nights seated around the large outdoor fireplace pit... the ideal location for entertaining family and friends. For 2015, a beautiful in-ground heated gunite pool has been constructed with water views from the in-pool benches.

Bed

Bath

Sleeps

$382.06

/ Nightly

Cottage

Charming, Renovated Island Cottage - Shelter Island License #: 012-2017

Shelter Island, New York, United States

This lovely 2 bedroom, 1 bath (plus an outside shower) renovated cottage located on a large lot in the center of Shelter Island is the perfect home base for your vacation. With all the amenities of home plus beach chairs, umbrella, rafts, towels, you'll be ready for a day at the beach and relaxation at home. Each bedroom is complete with a comfortable queen size bed, ceiling fan, antique dressers, and large closets. There is a double futon in the living area. 15 X 26 cedar deck overlooking the large back yard. Close proximity to restaurants, beaches, preserve for hiking, and kayak & bike rentals.brbrbrKeywords: vacation cottage, vacation home

Bed

Bath

Sleeps

$917.14

/ Nightly

Private Vacation Home

Shelter Island Waterfront Home!

Shelter Island, New York, United States

A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, pool and other areas of the home; this house is your vacation paradise. It has four bedrooms (comfortably sleeping 8), as well as four dedicated full bathrooms. With is also a den with a queen size fold out couch that can accommodate 2 additional people allowing the house to accommodate up to 10 people. Located on Shelter Island, only a three hour drive from Manhattan, and a short ferry ride from the east end of Long Island.brbrThis unique waterfront home features over 500 feet of private beach with stunning sunset views. Privately it is located at the end of a dead end street on the ocean/sound with a small adjacent boat ramp. During the day your private beach is perfect for beach fishing, minnow netting, kayaking, sailing, shell collecting or just relaxing with a book and watching the boats go by. The ocean/sound is tranquil and safe for children, with easy launching of kayaks or boats. Access to the beach is simply steps down from the pool/deck area onto the sand and ocean below. brbrAt night the home is the perfect place to watch a sunset, stargaze or enjoy the lights of the boats that go silently by in the ocean/sound. Shelter Island is far enough from the city and light pollution that you can even see the Milky Way.brbrYour family can enjoy the large yard between the house and the entrance road providing ample space for recreation. It is suitable for pickup football, soccer and yard games such as bocce or croquet. The island itself lends itself perfectly for those who enjoy biking as there are many roads throughout that provide the ability to ride through tree covered roads, stop at a beach or go into town for a bite to eat or drink.brbrA large patio overlooking the sound from the main living room is a large patio. Lounge chairs for sunbathing line this outdoor living area including table, chairs, couch for reading and outdoor grill. It’s a great place to sit with a cup of coffee in the morning watching the wildlife, or to enjoy the stunning sunsets with a glass of wine in the evening. brbrEntering the house through the entry vestibule, you walk into the main living room or into the main dining area with a table that seats 8; each with glorious views of the ocean. From the dining room you can enter into the kitchen that also has a small breakfast bar for relaxing. A washer, dryer, and dishwasher are provided here which make cleanup easy. Through the kitchen is either a formal den, complete with fold out couch and bathroom or alternatively going through a small hall, enter into the main TV room. It includes a flat screen TV that comes with a DVD player, stereo and the modem (WIFI included). brbrThe bedroom wing of the house has a homey charm. It was built in 1958 when the grandparents of the family made it their summer retreat. Two of the bedrooms have king-sized beds (one is comprised of two twins put together as a King and the other a full King), and one has two twin beds. The room with the King size bed and the 2 twin beds have a Jack and Jill bathroom; while the bedroom with a King bed has an ensuite bath with an ocean view. Another bedroom, off the kitchen is separately private with a private bath. brbrThe house is located about five minutes from the North Ferry from which it is another fifteen minutes to Greenport on North Shore of Long Island. Do some window shopping, grab a bite to eat, see a movie, and enjoy this delightful North Fork town, a historic center of 19th century whaling. To the South is Historic Sag Harbor, 25 minutes away by ferry, Easthampton’s boutiques 40 minutes away, and ocean beaches to catch some bigger waves are 40 minutes to 1 hour away. You can go to Montauk Point in an hour as well to hike around the park or do chartered fishing from either Greenport or the South Shore. The wineries, only some 20 minutes away, on both the North and South forks are also a great escape during the week that provide the fun of wine tasting along their routes lined with fresh farm/markets that sell fresh vegetables, pies, jams, corn and many other items. brbrOn the island itself, you are fifteen minutes away from Shelter Island Heights with its many restaurants, charming coffee shops, and quaint stores. On the way you can stop at the organic farm and education center at Sylvester Manor, the original 17th century manor house of the island. brbrYou’re also a ten minute drive from two of the best restaurants in the region (18 Bay and Vine Street Cafe) and a ten minute drive from a reasonably priced 2,500 yard public golf course. For the kids, it’s a scenic bike ride (or ten minute drive) to mini golf or one of two ice cream shops. Or for those young at heart, try the eclectic Sunset Beach renowned for its European flair and beach side location.brbrIf you like hiking, then Shelter Island is the place for you. One third of the island is a preserve known as Mashomack Preserve. Owned by the Nature Conservancy, the 2,100 acres shelter a large population of breeding ospreys as well as nesting populations of the endangered piping plover and least tern, as well as a number of rare plants.brbrAll of these delights and more await you in your stunning vacation rental. We’ll be waiting for you on the beach!brbrProperty Type br• House br• 3006 sq. ft. brAccommodation Type br• Vacation Rental brMeals br• Guests Provide Their Own Meals brOnsite Services br• Housekeeper Optional brSuitability br• Minimum Age Limit For Renters: 25br• Children Welcome br• Non Smoking Only br• Wheelchair Inaccessible brBedrooms: 4 Bedrooms, Sleeps 10, Beds for 10 br• Bedroom 1: 1 King br• Bedroom 2: 2 twins br• Bedroom 3: 1 King (made up of 2 twin beds) br• Bedroom 4: 2 twins br• Bedroom 5: 1 queen pull out couch brBathrooms: 4 Bathrooms br• Bathroom 1: toilet, combination tub/shower br• Bathroom 2: toilet, combination tub/showerbr• Bathroom 3: toilet, combination tub/showerbr• Bathroom 4: toilet, shower brbrOwner info:br brYear Purchased: 1958brAbout the owner: My grandparents bought this house in 1958 and it has been a beloved part of our family ever since. My siblings and I grew up spending every summer at this house, and as we grew up and had families the trend continued on a larger scale. brbrWhy the Owner Chose (Shelter Island Heights, NY, USA): brbrWho wouldn't want a large private beach and huge yard In 1958 it was a chance for my grandparents to buy a house that let them escape the busy city life they led. This property, between being in a quiet part of the island, and being waterfront, has the benefit of being simultaneously removed from everything, and extremely close to it. It has the dual benefit of being both private, so you can enjoy time to truly unwind, and also very close to shopping, restaurants, and public beaches so you can enjoy your vacation with family and friends. brbrThe Unique Benefits at this House: brbrA large private beach to fish, minnow net, boat, kayak, and generally relax on. Beautiful ocean views with a large deck so you can enjoy breakfast (lunch, dinner, and after dinner drinks) outside looking at the gorgeous water views. Huge yard for recreation (or laying on a blanket outside). Very private location but also no more than ten minutes away from anything. brbr

Bed

Bath

Sleeps

$759.77

/ Nightly

Private Vacation Home

Beautiful, quiet, private, short walk to the beach.

Shelter Island, New York, United States

This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking distance to Silver Beach off of Bootleggers Alley. We have bikes on hand to help you reach these and other beautiful destinations around Shelter Island. In the spacious backyard, which backs up to a nature preserve, you’ll find a brick patio with outdoor furniture, plenty of sun to sunbathe, lawn games, and an enclosed outdoor shower.br brThe master bedroom has a king-sized bed, en suite bathroom, and french doors that open to the serene privacy of the back yard. The second bedroom has a queen-sized bed, and the third bedroom has two twins – perfect for children or to share. Each bedroom has large closets and plenty of storage space. The hallway linen closet has towels for both bath and beach, sheets, and other comforts.br brThe living room, which features a large bay window, has a plush and comfortable couch and matching love seat that both pull out for additional sleeping space. The formal dining room has a sizable table that fits up to 10 guests and a set of french doors opens to the park-like back yard. The kitchen, which has great counter space, also has a benched bay window overlooking the backyard, and all the conveniences of home: a dishwasher, an oven, a Keurig coffee machine, a toaster oven, a microwave, and all the necessary items to cook and host. Just off the kitchen is a den that’s stocked with board games and an entertainment system, as well as a cozy, exposed brick gas fireplace. The den’s sectional sofa also pulls out to create another sleeping space. Finally, the laundry room has both a washer and dryer and is connected to the one car garage. Bookings over the summer months are Saturday to Saturday. brbr

Bed

Bath

Sleeps

$847.02

/ Nightly

Private Vacation Home

Shelter Island Retreat, 5 bdrms near everything!

Shelter Island, New York, United States

Bed

Bath

Sleeps

$924.17

/ Nightly

Private Vacation Home

Waterfront Estate on Shelter Island - 200 Feet of Waterfront - 100 Foot Dock

Shelter Island, New York, United States

Year round retreat on your own private waterfront estate with a meticulously renovated 1816 cedar shake house. Water views from almost every room! You will enjoy a private 2 acre parcel with a private dock on Shelter Island's beautiful Coecles Harbor. A covered entry porch opens to a delightful living room with fireplace, newly renovated kitchen, dining area, sunporch and deck. There is also a main floor master bedroom suite with spacious marble bath. The second floor features a 2nd master bedroom with ensuite full bath and private waterside balcony deck, plus two additional bedrooms and full bath. Sweeping lawns with sheltering trees lead gracefully to the waterfront dock. This wonderful property is the perfect summer retreat for swimming, fishing and boating enthusiasts. Strong Wi-Fi on both floors. 5G extender.brbr brbrKeywords: Two acres of beautiful waterfront with fully renovated waterfront house, with marble baths, large french doors facing the harbor, opening to a large deck. Very large yard to water 200 feet of waterfront in yard with dock.brbr brbr brbr brbrNOTE: There is no lifeguard on duty at our property. Swimmers swim at their own riskbr

Bed

Bath

Sleeps

$2281.57

/ Nightly

Private Vacation Home

Stunning Waterfront Estate House with 270 degree sea views on 7 private acres

Shelter Island, New York, United States

This stunning waterfront Estate House is a quiet paradise nestled in 7 private acres of nature on the pristine Menantic Peninsula. Enjoy strolls along the water’s edge or bask in the sun on the large plank stairs, which lead to a private, sandy beach area for frolicking, kayaking, and clamming. Marvel at magnificent sunsets nightly from the comfort of the seaside jacuzzi, or commune with hawks, herons and osprey in this peaceful nature sanctuary.brbrNewly renovated as of Spring 2020, this is the first year the Estate is open to stay. Scandinavian beauty meets modern luxury in this elegant, uplifting home. Every room offers panoramic sea views. Cathedral ceiling and copious skylights make heaven and earth meet. Sun-filled, spacious living and dining area are steps from the water. Open, ethereal kitchen offers marble counters, sub zero fridge, Viking gas stove, electric stove, and two dishwashers. White oak floors throughout make you feel like you are walking on a cloud. Also, two large balconies with water views, fully air conditioned with screens and shades throughout, laundry room on site.brbrExtremely convenient, the property is a five minute drive from the center of town, Sunset Beach and excellent restaurants.brbr- Palatial gas-powered fireplacebr-1/4 mile drivewaybr-Park like grounds with precious nature and wildlifebr-Surrounded by 350 ft bulkheadbr-Long deep water dock for fishing, boatingbr-Additional deep water mooring use for oversized water vehiclesbr-Convenient parkingbr-exterior security light and camera at front door

Bed

Bath

Sleeps

$1013.95

/ Nightly

Private Vacation Home

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island, New York, United States

Walk to Beach from this Bright and Comfortable 3 Bedroom / 2 Bath, Expanded Cottage. Weekly rentals available, please inquire. brThe open floor plan of the Kitchen, Dining Room and Living Room is enjoyed by all from morning until night. It has been said The Family room is one of the best napping destinations on the Island , surround by windows the room let the outside in, enjoy the wonderful relaxation of a summer breezes or fall afternoon by the fire. The deck, patio, heated pool and private yard are truly an extension of this home and a wonderful place to enjoy any part of the day. New Bathrooms and Comfortable Bedrooms complete this is a gem! brWe love: brShelter Island's restaurants are top notch and easy to experience. brHaving a relaxing lunch at The Pridwin's outside bar overlooking the water; brBiking to Crescent beach for a quick bite from the Islander's food truck; brA Sun and Sip on the lawn at the Rams Heads Inn; brLate afternoon live music at Shipwreck and White Oak Wine Bar . brDinner on the terrace of the Chequit. brGrab and Go at Vine Street Market, Marie's Kitchen and Elli Deli.brA Latte and Croissants at Height Cafe brLate night dancing at Sunset Beach. brbrAllow 1 dog of a non-shedding breed. No Cats brbrKeywords: Pool,Beach,Cottage,Sunset Beach, Shelter Island, Greenport, Sag Harbor, long weekend, short stay, Weekly Rental, pridwin, Chequit, Rams Head

Bed

Bath

Sleeps

$1237.27

/ Nightly

Private Vacation Home

Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!

Shelter Island, New York, United States

This Shelter Island beach house has all the necessary ingredients for a fabulous year-round getaway. Located on a shy acre just outside the Village of Dering Harbor, this sun-filled and spacious waterfront home is on a slight elevation, with 150-foot sandy beachfront and dock . The first level features an open living, dining and kitchen layout with magnificent water views. The kitchen was renovated in the last two years with custom cabinets, granite countertops, and high end appointments. A sunroom is just off the living room with views of the garden. The master suite overlooks the water and as a bonus has a porch for romantic evenings. Two additional bedrooms are on the first floor. The lower level is above grade and finished with a dorm style bedroom with sliders to the waterside grounds and full bath.

Bed

Bath

Sleeps

$927.67

/ Nightly

Private Vacation Home

Cozy Shelter Island all season Rental

Shelter Island, New York, United States

This family friendly private three-bedroom, two bathroom Silver Beach ranch house is perfect for any season. Enjoy the pool, covered porch and walking distance to beaches and bays, the large chef's kitchen and comfy living room with fireplace in cooler months.brbrThe house features a large, enclosed and private pool and garden area with gas grill and outdoor shower, as well as a great covered outdoor porch perfect for cocktails. There is also a quiet separated work studiobrbrThe house has a very large kitchen with every cooking accouterment and 8-10 seat table in kitchen . There is a comfortable living room equipped with a large smart TV, and wifi/cable. There is a washer/dryer in the basement and bedding and towels are provided. br Spend Fall and winter here watching the leaves turn and hanging out in the enclosed yard around the fire pit, roasting s'mores and staying cozy and warm. brbrThe house has a modern beach island feel on a quiet road. There is a semi private association beach close by as well as beautiful Shell Beach all in walking distance. Access to multiple beach outlets is the great part of this house. The house has a kayak, many bikes for kids and adults, fishing rods, and there is nearby access to sailing, boating, fishing, SUP, windsurfing, kiteboarding, etc.brbrTennis in local courts is available in many locations on the island, fun public golf course 1 mile away and a quaint Heights area with shops and restaurants 3 miles away.brbrOff island activities include shopping, antiquing, and touring the wine and farm country in the North Fork as well as dinning in Greenport, or easy access to Sag Harbor and the rest of the Hamptons via the South Ferry.

Bed

Bath

Sleeps

$911.56

/ Nightly

Private Vacation Home

Harbor-front gem w/ private beach and open property

Shelter Island, New York, United States

Spacious ocean front, two story home located in peaceful neighborhood on West Neck Harbor. Home is perfect for large families. Both first and second floor have two spacious bedrooms, full kitchen, full bath, and family/dining room. Two first floor porches and a second floor deck offer gorgeous harbor views. Additional outdoor shower makes after-beach rinses a breeze.brPlenty of driveway parking and one car garage. Private beach, a large lawn, grill, and Wifi offer a variety of activities.brOutdoor patio furniture on the second and first floor porch allow for scenic spots to enjoy your morning cup of coffee or a nice family meal. Open lawn is ideal for games and outdoor barbecues, make use of the charcoal grill (we require grills to be used only on the grass, not on any of the decks). The tranquil private beach is perfect for swimming, kayaking, fishing, sunbathing and any beach activity you prefer. If you have a boat, make use of one of the several boat launches near by and enjoy a day on the water. (Please note renters are not to make use of any of the owner's boats on the property or to move them from their locations. Items locked in the shed are for owner's use only.)

4

Bed

2

Bath

8

Sleeps

$981.85

/ Nightly

Private Vacation Home

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

Shelter Island, New York, United States

Your home away from home in Shelter Island with 4 bedrooms. This awesome house features 1 queen bed, 1 twin bed, 1 full bed, and 1 sofa bed, perfect for families or groups of friends. Enjoy the enchanting bathrooms with a shower, bathtub, and hair dryer. Stay cool with AC and stay connected with WiFi. We hope you'll enjoy your stay at our house. We are born and raised islanders who can also point you in the right direction for anything you are looking for during your stay out east!

4

Bed

2

Bath

14

Sleeps

$1418.86

/ Nightly

Private Vacation Home

Brilliant 4-bedroom house with heated pool in charming Shelter Island

Shelter Island, New York, United States

Shelter Island is waiting for you at this 5,000sq ft, all on one floor, 4-bedroom house. Inside, guests find 4.5 bathrooms featuring showers, bathtubs, and a jetted bathtub for ultimate relaxation. The bedrooms include 2 king beds, 1 queen bed, and 2 full beds, plus a living room with a comfy sofa bed. One of the king bedrooms is located in its own private wing with a kitchenette and it's own living room, perfect for guests and in-laws! With heating and air conditioning, the house stays comfortable no matter the season. The heated pool is just an added bonus! This tremendous space offers plenty of room to unwind and enjoy your time away. Make your holiday one for the books with a stay at our place.

Bed

Bath

Sleeps

$875.24

/ Nightly

Private Vacation Home

Shelter Island, NY Fully Renovated Farmhouse with Pool

Shelter Island, New York, United States

Enjoy Shelter Island in this fully renovated, designer interior farmhousebr3 BR / 2 BAbrThe house is air conditioned, 2nd bathroom has a jacuzzi tub.brSunbathe by the Private swimming pool, cook dinner on the garden and flower enclosed dining patio and relax by the outdoor fireplace or have an evening by the firepit next to the pool.brAn easy bike ride to one of Shelter Island's many beautiful beaches.brAny rainy days can be spent inside by 1 of the 2 indoor fireplaces, shopping in town or exploring the rest of the Hamptons.brbrbrbrKeywords: Summer House

Bed

Bath

Sleeps

$707.26

/ Nightly

Private Vacation Home

Mid-century on idyllic pasture like setting with pond

Shelter Island, New York, United States

This mid-century modern home sits on over an acre of land overlooking a tranquil pond. Located in the Shorewood section of Shelter Island just steps from a private beach and a 10 minute walk to the popular Wades Beach and access to a private tennis court across the street makes this a great summer escape. The open planned living room, dining room and kitchen with vaulted windowed ceiling adds great light by day and stargazing by night. All three bedrooms have sliding glass doors accessing the back deck and backyard. brbrThe furnishings are a mix of mid-century and modern, with white Egyptian cotton bedding in all three bedrooms. The master bedroom has a king bed, on suite bath and lots of windows and light. The second bedroom has a queen bed and lounging chair and the third bedroom has a twin sleep sofa, writing desk and chair, both rooms share a bath with shower in main hallway. Central air and ceiling fans in every room, make your stay comfortable.

3

Bed

2

Bath

5

Sleeps

Vacation Rentals By Owner In Shelter Island, NY

$480.52

$1626.7

$4312.94

$448.88

$1271.03

$2885.17

$382.06

$917.14

$759.77

$847.02

$924.17

$2281.57

$1013.95

$1237.27

$927.67

$911.56

$981.85

$1418.86

$875.24

$707.26

Rent a place that suits your needs

Most popular vacation rentals in Shelter Island

$924.17

$759.77

$805.85

$847.02

$855.50

$877.28

$1013.36

$1056.81

$1013.95

$752.47

Most Popular Cities in New York