Vacation Home Rentals By Owner In Shelter Island, NY

$717.71

Shelter Island - spacious 4 bdrm home near beach! Heavenly, peaceful oasis

Shelter Island, New York, United States

Spacious 4 bedroom, 2 1/2 bathroom home on heavenly Shelter Island. Minutes to beach and town. Overlooks a tranquil pond. Large grounds and deck, Kawai grand piano. Cathedral entrance, breakfast room, with bay windows, dining room, fireplace, laundry room, barbecue, air-conditioning, quiet cul de sac. Highest WiFi speeds with mesh system extension throughout the house. A perfect, rejuvenating retreat!

4

Bed

2

Bath

6

Sleeps

$1687.8

/ Nightly

Private Vacation Home

Beautiful Shelter Island/Hamptons Beach House Monthly Rental

Shelter Island, New York, United States

An absolutely amazing vacation property Come enjoy this very private and stylishly renovated beach house with beautiful coral stone floors offering spectacular sunrise to sunset water views on a long stretch of sandy beach. Set on West Neck Harbor with 3 waterside ensuite bedrooms plus a study with convertible sofa and 4 full bathrooms. In a very private setting, the house has an enclosed stone courtyard leading to the glassed entry which opens on to a spacious common area with views of the water from every air conditioned room. Vaulted ceilings in living area, fireplace, inside and outside dining areas plus fabulous kitchen with honed slate countertops, Top of the line Gaggenau appliances and walnut cabinets. The layout affords great separation for all bedrooms, each with direct access to outdoor water view space. A lovely second story master suite has a bath and deck with wonderful outdoor bathtub and birds eye view of the beach. The outdoor amenities include spacious covered deck areas, patios, outdoor fireplace, shower and kitchen. Enjoy your vacation in this magical seaside paradise sunning and swimming at the beach, reading or napping in the cool breezes on the deck to the sound of the waves lapping the shore; or barbeque at cocktail hour as the sun sets over sparkling water and indulge yourself with a romantic dinner under the stars or venture out to one of the wonderful restaurants on the island or in nearby Sag Harbor. This house has the benefit of prevailing breezes, spectacular views, modern amenities and an amazing location on the pristine Shelter Island yet within 4 minutes to the South Ferry and all that Sag Harbor and the Hamptons have to offer (short ferry) or 6 min to the North Ferry and all that Greenport and the North Fork offers. This property is a true gem. Monthly rental only but will consider 2 week rental.

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Sleeps

$675.98

/ Nightly

Private Vacation Home

Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve

Shelter Island, New York, United States

3 bedroom, 2 bath house in Shelter Island offers many amenities including pool, dock, private beach access and great coastal hiking in the 2,000 acre Mashomack Preserve. Close to the south ferry with easy access to Sag Harbor and the Hamptons. It is the perfect house to get away from the hustle of the city to relax, soak in the sun and enjoy the gourmet chef’s kitchen and herb garden and 2 grills.brThe open plan house has a granite eating counter, dining room and a large deck overlooking the pool with an outdoor dining and lounging. brThe large property comes with a paddle board and 4 bikes to explore the beautiful island.brThere are 3 bedrooms, including a master en suite.

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Bath

Sleeps

$1694.71

/ Nightly

Private Vacation Home

Scandinavian family home on the water

Shelter Island, New York, United States

A truly serene place, perfect for a family to wind down for a while.br3 bed, 2 bath on a one + acre waterfront with pool. We love waking up with the sunrise and go out on the paddle board, or enjoy a cup of coffee on the back deck. Near wades beach, and the neighborhood is very quiet and walkable.brbrThis is our year-round home that we rent out while traveling, we ask you to care for our home as you do for your own.

Bed

Bath

Sleeps

$1398.2

/ Nightly

Private Vacation Home

AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

Shelter Island, New York, United States

Discover the beauty of Shelter Island from this Award winning, Architect owned and designed, 4-bedroom estate. brbrWhether you're lounging by the fireplace in the cozy clearstory living room or enjoying the fresh air on the spacious iconic wrap around porch, this property is perfect for a relaxing carefree summer getaway. The First floor encompasses an open floor plan seamlessly connecting kitchen, dining, living room and cozy den spaces as well as a private master suite. Second floor has 3 additional bedrooms and bathroom with access to an exterior observation deck perfect for bird watching with an early morning coffee. Guests will also have access and use of the first floor to the accessory 2 car garage structure on the property. brbrThis Property is located within a prominent Hamptons style estate area of the Island and within walking distance to multiple beaches. Bicycles, kayaks and paddle boards can be rented on island if so desired. And don't forget to take a hike at the Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, it is not to be missed. brbrWe hope you'll enjoy your stay at our estate.brbrNearby Beaches:brShell Beach, Crescent Beach (Sunset Beach), Crab Creek Beach, Bootleggers Alley Beach.brbrNearby Grocery Stores:brIGA brbrNearby Restaurants and Bars:brDan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jars.brbrMarie Eiffel- in the Heights a wonderful great take-out food.brbrRam's Head Inn- always special even just for cocktails on the beautiful lawn in Adirondack chairs.brbrKyles- fantastic homemade jelly and cinnamon doughnuts croissants and cakes.brbrCommander Cody's- great fish store, and fabulous barbecue- pan fried chicken, and take out fish.brbrVine Street Cafe- excellent food, five stars.brbrMaria's kitchen- great take out Mexican- great homemade chips and guac.brbrShelter island slice for pizza.brbrChequit- in town.brbrSaltbrbrLeon 1909

4

Bed

2

Bath

9

Sleeps

$1602.18

/ Nightly

Private Vacation Home

Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...

Shelter Island, New York, United States

Please note that a reservation for this property needs to be approved before it is confirmed.brbrGreat Circle SerenitybrbrTennis Court, Open and Spacious Living and Dining Areas, Close Proximity to Beachbrbr5BR/4BA w/ Living Room & Fireplace, Dining room, chef's kitchen, heated in-ground gunite pool and tennis court.brbrDid someone say private pool and tennis court We did! This home is the perfect getaway for those looking to continue their active lifestyle all throughout their vacation. Circle drive features a private tennis court with a basketball hoop and a fenced-in private pool. Spend the afternoon grilling on the massive deck where guests can enjoy the summer sun. If that isn't enough, take a stroll down to the beach and enjoy the salty Peconic River.brbrThis property has a max occupancy of 10brbrBedroomsbrbrBedroom 1: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, ClosetbrbrBedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, TV, Closet, Balcony/DeckbrbrBedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, ClosetbrbrBedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, TV, ClosetbrbrBedroom 5: One Double/Full Bed, 2nd Floor, Air Conditioning, TV, ClosetbrbrAdditional Sleeping Space 1: One King Bed, Guest House 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet, PrivacybrbrBathroomsbrbrBathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower, TubbrbrBathroom 2: Full Bath, First Floor/Main Floor, Shower, TubbrbrBathroom 3: Full Bath, 2nd Floor, ShowerbrbrBathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, TubbrbrTVsbrbrBedroom 2brbrBedroom 4brbrBedroom 5brbrOutdoors & Pool/SpasbrBeach Chairs, Outdoor Shower, Lounge Chairs (8 Chairs), Deck/Patio, Balcony, Patio Furniture (Table, Chairs, Umbrella), Bicycle (2 Adult Bikes, 4 Children Bikes), Grill (Gas), Tennis Court (Private), Tennis Equipment (Rackets), Fence Around The Pool, Private Pool (Outdoor, Heated, Saltwater)brbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning, Heating, Iron/Ironing Board, Washer, Dryer, Usable Fireplace (Wood-Burning), Internet (Wifi), Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Blender, Ping Pong Table, Speaker System (Bluetooth Speaker, Sonos), Television, Private Entrance, Parking (6 Cars In Driveway), Garage (2 Cars In Garage), Living Room, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Laptop-Friendly Workspace, Pots and PansbrbrOther FAQ'sbrbrPool Fenced In: YesbrbrBackyard Fenced In: YesbrbrEstimated Square Footage: 2,500brbrSuitability: Not handicap accessible.brPrimary renter must be at least 30 years old.brbrUtility Disclaimer:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $115.00 per night of the reservation.brbrCleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.brbrAdditional Guests: Additional persons are prohibited unless express approval is provided.brbrEvents Policy: Events are prohibitedbrbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: A refundable cash security deposit of $3,000 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in.brbrThis property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

5

Bed

4

Bath

10

Sleeps

$603.89

/ Nightly

Private Vacation Home

Cozy waterfront Shelter Island house with panoramic views. Pet-friendly!

Shelter Island, New York, United States

Discover the calming beauty of Shelter Island from this 3-bedroom house overlooking Menantic Creek. Enjoy sweeping vistas of the water from the three-season porch while eating your meals, reading, or relaxing with friends. Stairs provide easy access to a waterfront where your family can play, fish, boat, or swim. Mature trees shade a front lawn large enough for children's games or eating al fresco. The house is pet-friendly so bring your dog(s) or cat(s)!brbrEnter the house through a front porch that captures delightful water breezes and into an eat-in kitchen with a full range of amenities, including a French door refrigerator. A comfortable living room with television opens up to the three-season porch in the back. The first floor also has an en-suite double bedroom and private full bath. Upstairs two bedrooms share a full bath, the master with a queen bed and ample closet space and another with twin beds. brbrOur house can be your Shelter Island playground. Children will spend hours at the easily accessible water's edge fishing, swimming, splashing, and playing. Your family can choose among 6 kayaks and a canoe to explore inside and outside the creek. Access Wades Beach and the Fresh pond with a 3 minute drive or 15 minute walk/paddle, or just take a dip in Menantic creek behind the house. Spend early evenings facing west over the water watching amazing sunsets from your perch on the water. Drive less than two miles to access food and liquor stores, restaurants, and the long walking trails in the pristine Mashomack Preserve.

3

Bed

2

Bath

6

Sleeps

$1304.36

/ Nightly

Private Vacation Home

Idyllic 4-bedroom family home in charming Shelter Island

Shelter Island, New York, United States

Located in Shelter Island’s Hay Beach and set on nearly an acre of land, this recently renovated home offers bay views and easy access to a sandy beach brbrKey features:br- double-height ceilings leading to the living and dining areas, br- fantastic natural light in every room of the house!br- outdoor entertainment deck overlooking the lawn br- Newly installed 16 x 40-foot saltwater Gunite pool complete with pool inflatables and accessories. br- Picture-perfect kitchen with Bertazzoni appliancesbr- A first floor en-suite bedroom - perfect for guestsbr- Two further bedrooms upstairs share a hallway bathroom,br- Master en-suite primary bedroom offers with a new full bath. br- The lower level basement provides plenty of further recreational space including games and toys, art supplies, exercise equipment, beach and garden games, bikes and paddle boardsbr- Indoor and outdoor fireplacesbr- High speed fiber internet, with coverage across the propertybr- Located close to five sandy beaches, Dering Harbor Village, and Gardiners Bay Country Club,

Bed

Bath

Sleeps

$1056.81

/ Nightly

Private Vacation Home

Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12

Shelter Island, New York, United States

Welcome to Casa di Famiglia! Close to nature and the water, this family compound will rejuvenate your spirit. This property consists of a 3 bedroom 2 bath farmhouse that sleeps 6 including a queen pull out couch in the office. Also on the property is a 3 bedroom 1 bath pool house that sleeps 6 and has a living area with a kitchenette. The pool house is open from June 1st to October 15th. There is a lovely, private heated pool and a beautiful private backyard for relaxing and playing games. Enjoy morning coffee on the side porch and in the evening sit by the outdoor fire on the patio. Included in the rental are bikes to enjoy cycling around this beautiful island and kayaks to launch only 1/4 mile down the road. This property borders town nature walking trails ideal for viewing the diverse wildlife in the area. A water front restaurant, bar and The Island Boatyard Marina are walking distance from the house. This island is a boating paradise with boating charters available at the marina. The beach is a 5 minute drive. Between listening to all the bird song, smelling the salt air and relaxing in this most serene space, your visit to Casa di Famiglia will be a memorable one!

Bed

Bath

Sleeps

$652.98

/ Nightly

Private Vacation Home

Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island Hts

Shelter Island, New York, United States

Architecturally designed 1,800 sq. ft. contemporary home. Three bedrooms, two bathrooms. Situated on a quiet country road, one-half mile to Wade’s Beach. Wooded property (2.10 acres) with a large backyard. Open first-floor plan with new stainless appliances. Jacuzzi in large upstairs master bedroom with walk-in closet. Excellent for cooking and entertaining. Front porch that looks out on nature preserve and screened back porch, including new Weber grill. Clean, modern peaceful summer home, perfect for relaxation and entertaining guests.brbrbrbrKeywords: Modern, architecturally designed cottage on quiet country road

3

Bed

2

Bath

7

Sleeps

$663.38

/ Nightly

Private Vacation Home

Water views, paradise for a month on lovely shelter island for July

Shelter Island, New York, United States

Enchanted beach house with pool on a private road. No pretentious rules, simple island life close to nature.brVery Safe, families welcome. Enough space for help. No pets at this time.br Beautiful, quiet brWalk to beach

4

Bed

2

Bath

8

Sleeps

$1798.9

/ Nightly

Private Vacation Home

unbelievable water views, 50' heated pool and private beach

Shelter Island, New York, United States

Feel like you are on a luxury cruise ship! brBeautiful Shelter Island three bedroom/ three bathroom home. brLarge living room/dining room, two car garage. The home has unobstructed expansive views of Peconic Bay. This bright and airy house faces southwest towards 50' pool and private sandy beach with incredible sunsets. Pool perfect for swimming lapsbrPrivate fenced yard with outdoor shower, and gas BBQ. brPerfect summer rental.

3

Bed

3

Bath

6

Sleeps

$1723.6

/ Nightly

Private Vacation Home

Waterfront Victorian farmhouse with heated pool and deepwater dock

Shelter Island, New York, United States

4,000 sq ft waterfront family home on 3 acres. Plenty of space for the whole family! Our home maintains the traditional charm of a late 19th century farmhouse. If you love vintage houses with an elegant, boho feel, a huge porch to gather with friends and watch spectacular sunsets over the creek, daily swims in our heated gunite pool while gazing out over the water, kayaking/boating and fishing off the dock, a trampoline for fun, our family-oriented house is for you!

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$2020.5

/ Nightly

Private Vacation Home

Huge Island Getaway Pool Hot Tub Walk To Beach

Shelter Island, New York, United States

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.brbrWhat our guests love about the space: brbrEscape to island paradise at this luxurious designer vacation home, nestled in the heart of mature landscaping so you can unwind in your private huge heated gunite pool. The house has an open floorplan that feels huge with an indoor/outdoor feel that makes it great for entertaining, with plenty of room to hang out with your family and friends and still retreat to your private, enormous bedrooms with extremely comfortable beds. The house also features a finished basement that is great fun for kids and adults alike, with a movie theater and a pool table. Wake up to the seaside air and spend your days basking in the sun, surrounded by breathtaking and relaxing open green views of the nature reserve. Walk to some of the top rated restaurants on the island (Salt, Leon, Chez Maries), a short stroll to get ice cream at Tuck Shop, or simply take a leisurely bike ride to excellent Wades or Sunset Beach. After a day of hiking, sunbathing or beachcombing, come back home to cozy up in the living room or basement for a movie or game night, by the crackling fire, or have a glass of wine in the bubbling hot tub under the stars, taking in the serene beauty of the surrounding nature reserve. This is the ultimate luxurious seaside getaway to make the most unforgettable memories with your loved ones. brbr About the housebrbrThere are three master bedrooms with en-suite bathrooms, one in a private building or separate wing connected by a walkway - great for someone who wants privacy or a nanny / in-laws. Lots of room for entertaining - a beautiful sunroom with a round table, a long outdoor table overlooking the peaceful nature reserve, and an indoor table. The group can be together and interacting but still have privacy. Imagine the breeze coming in from lots of french doors opening to decks, overlooking the pool, but yet shrouded by tall trees so you are in your own private, green, pool oasis. Rooms and portions of the house are connected by walkways (you can also walk inside of course), so you really feel a bit like you're at a glam summer camp - GREAT for family or large groups, as you can host but still retreat to privacy.brbrThe center of the house is through french doors into a beautiful long table overlooking the private, green, nature preserve. Nothing is more calming than eating overlooking the pool and those gorgeous lawns as the birds chirp or you may sight a deer or two - dogs love running on the lawn! You have these views from a beautiful breakfast room even in the winter. brbrA great place for your family and groups to make unforgettable memories and spend quality time together. brbrMaster 1: King size bed, huge vaulted ceilings, en suite bath with tubbrMaster 2: Queen size bed, amazing light, private deck overlooking green laws, en suite bath brMaster 3: In separate wing, king sized bed, en suite bath, tons of space, huge private deck overlooking greenerybrBedroom 4: Queen sized bed, bathroom right outside door, beautiful views of the lawns and pool. brBedroom 5: Two twin beds and extra trundle bedbrBonus Bedroom 6: Queen Bed (please note this room has pocket doors for privacy), huge deck overlooking lawnbrLiving Room with Wood Burning Fireplace, Huge Couch, Big French Doors overlooking DeckbrDining Room for 12-14, open to Gourmet KitchenbrGourmet Kitchen with Wolf Stove + Cooking SuppliesbrBasement: Theater with Projector, Big Pool Table - kids love it brOutdoor: Huge Gunite Pool, Ping Pong, Dining for 12-14 overlooking the nature reserve, outdoor grill, HOT TUB that is piping hot all year round. brbr***COVID update: The house is cleaned by covid-certified cleaners, has excellent wifi, and is private with a secluded beach nearby****brbr2024 DATES are now open with most of the summer booked! Book as the best houses go early :) : Weekly rates below. Please contact me directly if you would like to book. brbrSummer - Almost Fully Booked!! Last Availability Going Fast brMay 27 - Jun 2 (6 nights) - 15K brJune 9 - June 30 - 16K/week, or 45K for the month brJul 30 - Aug 4 (5 nights) - 14K br*May, September and October on the island are also wonderful value*brbrOther Months brFebruary, March - $4K weeklybrApril - $6K weeklybrMay - $11K weeklybrSeptember - $11K weeklybrOctober - $7K weeklybrNovember- $5K weeklybrDec - $5.5K weeklybrbrEverything! It's all yours with tons of privacy thanks to huge green trees on all sides of the property.brbrHelp is always available with quick response time. Our house manager, Kim, lives next door and is a favorite with our guests.brbrShelter Island: “an emerald jewel set in the bracelet of turquoise waters.” An easy five minute ferry ride from Sag Harbor and all the Hamptons has to offer yet once you get on the ferry, your shoulders relax, there is little traffic, beaches are serene and not overly crowded, yet there is much happening - try Sunset Beach, from Andre Balazs, the owner of The Standard and Chateau Marmont, where you feel like you are in the south of France (really!), or Salt, Leon [both walking distance] or the Vine Street cafe for great food. Tons of gorgeous beaches including the blissful Wade's Beach which we are incredibly close by to. For those that don't know Shelter Island, it is an 'insider's secret' - it manages to be unbelievably relaxed, low key and surrounded by nature and the quaint and charming whitewashed architecture of the Heights, yet a 15 minute drive to Sag Harbor or the North Fork so you can enjoy everything about the Hamptons or Greenport! Our guests love that the best lobster roll in town is at Salt, which is literally next door to the house, and is great when you need to cater a party in a pinch. Chanel and Marni chose to host their summer pop ups on Shelter Island for a reason - it is a very special place, that manages to be nostalgic, glamorous, serene and low key all at once :) Just read our reviews!brbr5 minute ride from the ferry. Few steps away from the water - at the end of our street! Prime location but still serene with lots of privacy - walking distance to Salt (bring lobster rolls home and eat on your patio!) and Leon restaurant, Tuck Shop ice cream shop, and Chez Marie's. Walk to the dock or bike to Wade's beach, town or Sunset Beach. Go for a relaxing hike in nearby Mashomack Nature Reserve. 5 minute drive to pretty much anywhere on the island. 16 minutes door to door to Sag Harbor! Or, explore the wineries in Greenport, also just a few minutes drive again. You truly have the best of both worlds on Shelter Island - you can be in the thick of things on the North or South Fork, and still come back to a peaceful sanctuary surrounded in nature in just a few minutes.brbrPlease note pool is open in the warmer weather months (usually open sometime in late April and close in early October), not the winter months, but hot tub is piping hot and available year round :) brbrPlease note we love pets and they are very welcome, but there is a $195 fee per pet. Please do let Kim, our house manager know if you plan to bring your pet :)

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Sleeps

$599.81

/ Nightly

Private Vacation Home

Hilltop Cottage Privacy Abounds

Shelter Island, New York, United States

Private Hilltop Cottage on 1.5 acre lot bordering horse farm. Feel the stress melt away. brCentrally located within walking distance to restaurants, golf, and beach. Clean, cozy, 3 bedroom with 2 full baths, wood stove, grill, washer & dryer, full kitchen, and dining room. Bikes and games, too.

3

Bed

2

Bath

6

Sleeps

$1228.16

/ Nightly

Private Vacation Home

Relax at a private beach! Three bedrooms await you near Shelter Island beaches!

Shelter Island, New York, United States

Tranquil getaway in Shelter Island with private beach access. Modern, bright home newly decorated by top design firm is a 2 min drive or 30 min walk from Crescent/ Sunset Beach, the Pridwin, Leon. Near Wades Beach, Shelter Island Heights.brbrHouse officially has 3 bedrooms, but the finished basement effectively acts as a 4th bedroom. House has central a/c, multiple decks & outdoor spaces to relax and dine, and is fully equipped with new grill, cookware, appliances, beach chairs & towelsbrbrPrivate beach is ideal for swimming, kayaking, paddle boarding or sunset drinks at a picnic table.

3

Bed

2

Bath

10

Sleeps

$1042.18

/ Nightly

Private Vacation Home

Serene Shelter Island Getaway: House + Guest Cottage Steps from the Water

Shelter Island, New York, United States

Escape to a peaceful Shelter Island retreat just moments from the water. Perfect for families and groups, this charming 5-bedroom property includes a main house plus guest cottage with space to relax, gather, and play.brbrThe home comfortably sleeps guests with 1 king bed, 3 queen beds, and a bunk room kids will love. Enjoy three full bathrooms plus an outdoor shower, ideal after beach days and paddleboarding adventures.brbrSpend your days launching kayaks and paddleboards from nearby beach access just steps away, or a 10 min walk to Reel Point beach, then come home to sunset dinners on the expansive deck. Kids can enjoy the playset and finished basement entertainment room while adults unwind upstairs. Or hang on the huge deck around the outdoor fire table with s’mores under the stars.brbrInside, cozy up by the wood-burning stove after a day exploring Shelter Island’s beaches, farm stands, restaurants, and nature preserves.brbrLocated walking distance from the iconic Ram’s Head Inn for dinner or Bocci ball. This home offers the perfect balance of relaxation, adventure, and classic island charm.brbrWhether you're planning a summer getaway, family gathering, or quiet weekend escape, this is your home away from home on Shelter Island.

5

Bed

3

Bath

10

Sleeps

$1737.26

/ Nightly

Private Vacation Home

Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!

Shelter Island, New York, United States

Shelter Island PreservebrbrBeautiful Shelter Island Getaway on over an acre, minutes from the ferry!brbr4BR/3BA + an additional sleeping space, private heated pool, outdoor shower, BBQ, total privacy, surrounded by naturebrbrWelcome to your perfect Shelter Island getaway, Shelter Island Preserve! This beautiful 4 bedroom, 3 bathroom home with an additional sleeping area is perfect for families and friends looking to escape from daily life. Located just minutes from the ferry, this is the ultimate Shelter Island getaway!brbrStep inside and you'll immediately feel at home taking notice of the open layout that's filled with natural light. The living spaces easily flow from one room to another, making it perfect for entertaining and spending time with family and friends. The kitchen is a chefs dream, boasting top-of-the-line appliances and multiple sitting areas for everyone to gather around.brbrWhen it's time to head outside, you'll be greeted by total privacy on the over 1 acre property. Take a dip in the heated pool, relax on the loungers or sink into the comfortable couches surrounding the pool. The outdoor BBQ is perfect for whipping up a delicious meal under the stars. There's even an outdoor shower to wash off after a sand-filled day at the beach.brbrUpon returning after a day exploring town, sitting on the beach, or just catching rays by the pool, retreat to one of the four beautifully appointed bedrooms, each equipped with fresh linens and all the essentials you need for a comfortable stay. Don't forget about the additional sleeping space providing extra room to make everyone feel comfortable. With three bathrooms, everyone will have the space they need to get ready for the day ahead.brbrShelter Island Preserve is conveniently located near Shelter Island's art galleries, restaurants, town and beaches, and conveniently just minutes from the ferry. This home is sure to provide you with everything you need to have an experience and build memories that will last a lifetime.brbrThis property has a max occupancy of 10brbrBedroomsbrbrBedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Standard ClosetbrbrBedroom 2: One Double/Full Bed, 2nd Floor, Air ConditioningbrbrBedroom 3: One Double/Full Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, TV, Standard ClosetbrbrAdditional Sleeping Space: One Double/Full Bed, 2nd Floor, Air ConditioningbrbrBathroomsbrbrBathroom 1: Full Bath, 2nd Floor, Ensuite, ShowerbrbrBathroom 2: Full Bath, 2nd Floor, ShowerbrbrBathroom 3: Full Bath, First Floor/Main Floor, Handicap Accessible, Shower, TubbrbrTVsbrbrBedroom 1brbrBedroom 4brbrOutdoors & Pool/SpasbrDeck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Outdoor Shower (Hot + Cold Water), Bicycle (1 Adult Bikes), Beach Chairs (4 Chairs), Beach Umbrella, Cooler, Fence Around The Yard, Private Pool (Outdoor, Heated, Freshwater)brbrAmenitiesbrBed Linens, Bath Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Main Living Room), Parking (5 Cars In Driveway), Iron/Ironing Board, Wine Fridge, Ice Maker, Coffee (Pot), Toaster, Blender, Smart TV, Speaker System (Sonos), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, EssentialsbrbrSuitability: Not handicap accessible.brPrimary renter must be at least 35 years old.brbrPet Policy: Pets may be allowed but are subject to owner's approval (please inquire). Pet approval may include additional fees and/or security deposit.brbrUtility Disclaimer:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $135.00 per night of the reservation.brbrCleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.brbrAdditional Guests: No additional persons beyond the max occupancy of this listing are permitted.brbrEvents Policy: Events are prohibitedbrbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

5

Bed

3

Bath

10

Sleeps

$1856.56

/ Nightly

Private Vacation Home

Family Friendly Oasis Steps to Water - Heated Pool

Shelter Island, New York, United States

Enjoy the peaceful oasis of Silver Beach from this casual, airy, 6-bedroom home. The house sits on a quiet street, perfect for long walks and bike rides. Only minutes' walk to Shell Beach and seconds to boat landing. We have 2 tandem kayaks located at the water for you to explore West Neck, Menantic, and Dickerson Creeks. Three bedrooms upstairs and three down, the space is perfect for two families traveling together or a single-family that likes to spread out. Two TVs, deck with grill, fast Wifi. New bedding in all rooms. Beautiful home, only a minute’s walk to kayaks, and a short stroll to one of Shelter Island’s most beautiful beaches. brbrPrice is inclusive of utilities. Cleaning and pet fees additionalbrbrNote we have a one week minimum stay policy during our peak season (June - August). Ten (10) adult capacity is strictly enforced due to insurance limitations.brbrPlease enquire about long term stay discounts during the off season!

6

Bed

3

Bath

12

Sleeps

$1952.11

/ Nightly

Private Vacation Home

Shelter Island 4 bedroom waterfront home with home office

Shelter Island, New York, United States

Sunny and bright spacious home with 4 bedrooms, 2 living rms, laundry and office.brPerfect home to enjoy any seasonbr6 min from ferrybrlocated on Menantic Creekbrbedroom 1 has king bedbrbedroom 2 and 3 have queensbrbedroom 4 has 2 twinsbrthere is also a day bed outside the bedroom areabrmaximum 8 adults brbrThis house also has a home office to accommodate todays life stylebrthere are 2 living rooms br2 1/2 bathroomsbrlaundry roombrall bed linens and towels are suppliedbrthe kitchen is fully equipped with dishes, flatware, pots, pans etcbrbrthere are 2 parking spots any additional cars with have park at the ferrybrthis home is also equipped withbr2 bicyclesbr2 kayaksbr2 paddle boardsbrbeach chairsbrbeach umbrellabrbrplease bring your own beach towels our towels are not to leave the inside of the housebrthere will be no hosting of parties

4

Bed

2

Bath

10

Sleeps

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