[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Work and Play Special! Extended Stay Discount Vacation home in Shelter Island with private pool and kitchen ![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/a1d1bd69.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Experience the best of the Hamptons at this charming 1700’s cottage, nestled on 7 private acres. Dive into relaxation mode with a heated saltwater gunite pool, unwind on the screened-in-porch or enjoy an invigorating outdoor shower. 10 Exceptional ### Entire home 5 bedrooms1 bathroomSleeps 10 ## Popular amenities - - - Dryer - Washer - Parking available - Kitchen ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Work and Play Special! Extended Stay Discount Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this charming 1700’s cottage nestled on 7 private acres of lush greenery adorned with majestic trees-your very own oasis! There are steep steps up to the second floor. \* Excellent Wifi: Say goodbye to buffering and hello to productivity with top-notch Wifi, ensuring seamless work-from-home sessions! \*Poolside Paradise: Dive into relaxation mode with a heated saltwater gunite pool-the ultimate spot to soak up the sun and splash around. Plus, keep an eye out for our resident turtles and frogs in the pond! Propane usage will be charged after stay. \*Cozy pool house: Need extra space? Our pool house offers an additional bedroom, kitchenette and a half bathroom-perfect for guests or a private retreat! \* Outdoor Delights: Rinse out in style with an invigorating outdoor shower, then unwind on the screened-in-porch-an ideal spot for sipping your morning coffee or enjoying evening cocktails. \*Modern Comforts: This cottage is equipped with all the bells and whistles, including a recently installed chef's kitchen, A/C, heating, and a Sonos sound system-ensuring your stay is as luxurious as it is comfortable. \*Beach Bonanza: Just a ten minute stroll lies Wades Beach, beckoning you with its sandy shores and sparkling waters-paradise found! With room to accommodate up to 10 guests, this dreamy cottage is your ticket to an unforgettable Hamptons getaway. So grab your bags, grab your laptop, and get ready to blend work with pleasure like never before! Ahhhh Shelter Island!! ## Property amenities ### Beach - Beach nearby - Beach loungers - Beach towels ### Pool/Spa - Heated pool - Outdoor pool - Private pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Kitchen island - Kitchenette - Lobster/crab pot - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 0.5 bathroom - Bathtub or shower - Hair dryer - Outdoor shower - Shampoo - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Smart TV with cable/satellite channels - Stereo ### Outdoor areas - Barbecue grill - Garden - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Welcoming dogs only - One pet total ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Phone - Safe ### Location highlights - Near the bay - Near the marina ### Things to do - Heated pool - Table tennis - Birdwatching nearby - Cycling nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Kayaking nearby - Motor boating nearby - Sailing nearby - Swimming nearby - Wildlife walks nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit ### General - Garden - Housekeeping (on request) ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/119000000/118640000/118631900/118631875/c791f5a2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres Shelter Island - Pet-friendly - Air conditioning - Parking available - Barbecue grill [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=118631875&PinnedHotelID=118631875&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76430000/76420400/76420400/53a2a099.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly Silver Beach - Pool - Kitchen - Washer - Dryer 10 Exceptional 16 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=76420400&PinnedHotelID=76420400&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/w6016h4012x0y0-a337bac6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen East Hampton - Pool - Kitchen - Washer - Dryer 10 Exceptional 95 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=34146658&PinnedHotelID=34146658&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/34000000/33996200/33996173/567faece.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront House With Dock And Private Beach Shelter Island - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 22 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=33996173&PinnedHotelID=33996173&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton - Pool - Hot tub - Kitchen - Washer 9.8 Exceptional 32 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=101877657&PinnedHotelID=101877657&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/67000000/66130000/66121300/66121299/8f42b0a9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport! Greenport - Pool - Kitchen - Washer - Dryer 10 Exceptional 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=66121299&PinnedHotelID=66121299&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116770000/116761500/116761460/14261595.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Shelter Island Spacious Getaway with Cozy Fireplace Hay Beach - Kitchen - Washer - Dryer - Pet-friendly 8.0 Very good 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=116761460&PinnedHotelID=116761460&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor spa tub](https://images.trvl-media.com/lodging/36000000/35040000/35037700/35037604/2db832c2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day Peconic - Pool - Hot tub - Kitchen - Washer 9.6 Exceptional 138 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=35037604&PinnedHotelID=35037604&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/39000000/38280000/38273400/38273326/c3065089.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Huge Island Getaway Pool Hot Tub Walk To Beach Menantic Creek - Hot tub - Kitchen - Washer - Dryer 10 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=38273326&PinnedHotelID=38273326&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautifully farmhouse Southold - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 3 reviews CA $837 CA $1,629 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-07&endDate=2025-10-08&selected=113098265&PinnedHotelID=113098265&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 27 ### Check-out Check-out before 11:00 AM Contactless check-out available ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Rules Absolutely no parties or events of any kind. ### Pets Pets allowed Service animals are welcome, and are exempt from fees Welcoming dogs only 1 total pets ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Long-term renters welcome Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a first aid kit This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as Vrbo Property Private Hamptons Cottage Private Hamptons Cottage with excellent WiFi! Shelter Island ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C41.05247%2C-72.32422&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=ldY40V91EwpipbxzKS7-t9e8KZY=) Shelter Island, NY #### What's nearby - Wades Beach - 14 min walk - 1.2 km - Mashomack Preserve - 3 min drive - 2.5 km - Gardiner's Bay Country Club - 7 min drive - 5.9 km - Sunset Beach - 8 min drive - 6.0 km - Sag Harbor Marine Park - 15 min drive - 7.2 km #### Getting around - Greenport Station - 26 min drive - East Hampton, NY (HTO) - 37 min drive #### Restaurants - ‪Sunset Beach Restaurant - ‬7 min drive - ‪Vine Street Cafe - ‬16 min walk - ‪Stars Cafe - ‬6 min drive - ‪Opties & Dinghies - ‬4 min drive - ‪Pridwin Hotel - ‬8 min drive ## Frequently asked questions ### Does Work and Play Special! Extended Stay Discount have a pool? > Yes, this property has an outdoor pool. Pool types include heated pools. ### How much does it cost to stay at Work and Play Special! Extended Stay Discount ? > As of Oct 5, 2025, prices found for a 1-night stay for 2 adults at Work and Play Special! Extended Stay Discount on Nov 5, 2025 start from CA $1,116.16, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. [Choose your dates](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information?rfrr=HOT.HIS.question.link.click) for more accurate prices. ### Is Work and Play Special! Extended Stay Discount pet-friendly? > Yes, this property allows dogs (limit 1 total). ### What time is check-in at Work and Play Special! Extended Stay Discount ? > Check-in begins at 4:00 PM. ### What time is check-out at Work and Play Special! Extended Stay Discount ? > Check-out is at 11:00 AM. ### Where is Work and Play Special! Extended Stay Discount located? > Situated near the beach, this vacation home is within 1 mi (2 km) of Wades Beach, Havens House, and Shelter Island Historical Society. Mashomack Preserve and Shelter Island Whale's Tail are also within 2 mi (3 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Expedia's Latest Trends ### Hotels > [Seneca Allegany Resort & Casino](https://www.expedia.ca/Salamanca-Hotels-Seneca-Allegany-Resort-Casino.h2238839.Hotel-Information) > > [Golden Arrow Lakeside Resort](https://www.expedia.ca/Lake-Placid-Hotels-Golden-Arrow-Lakeside-Resort.h3164.Hotel-Information) > > [The Lake House on Canandaigua](https://www.expedia.ca/Canandaigua-Hotels-The-Lake-House-On-Canandaigua.h49087717.Hotel-Information) > > [Hampton Inn & Suites Lake Placid](https://www.expedia.ca/Lake-Placid-Hotels-Hampton-Inn-Suites-Lake-Placid.h6257605.Hotel-Information) > > [Six Flags Great Escape Lodge & Indoor Waterpark](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) > > [Duck Lake Campground](https://www.expedia.ca/Syracuse-Hotels-Duck-Lake-Campground.h12599916.Hotel-Information) > > [1000 Islands Harbor Hotel](https://www.expedia.ca/Clayton-Hotels-1000-Islands-Harbor-Hotel.h7484927.Hotel-Information) > > [Holiday Inn Resort Lake George - Adirondack Area by IHG](https://www.expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) > > [Crowne Plaza Lake Placid by IHG](https://www.expedia.ca/Lake-Placid-Hotels-Crowne-Plaza-Lake-Placid.h26787.Hotel-Information) > > [The Kartrite Resort & Indoor Waterpark](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) > > [Best Western Summit Inn](https://www.expedia.ca/Niagara-Falls-Hotels-Best-Western-Summit-Inn.h5183.Hotel-Information) > > [Hampton Inn Niagara Falls/Blvd](https://www.expedia.ca/Niagara-Falls-Hotels-Hampton-Inn-Niagara-FallsBlvd.h7532268.Hotel-Information) > > [Holiday Inn Express Hotel & Suites Watertown-Thousand Island by IHG](https://www.expedia.ca/Watertown-Hotels-Holiday-Inn-Express-Hotel-Suites-Watertown-Thousand-Island.h1532633.Hotel-Information) > > [Akwesasne Mohawk Casino Resort and Players Inn](https://www.expedia.ca/Hogansburg-Hotels-Akwesasne-Mohawk-Casino-Resort.h6009138.Hotel-Information) > > [High Peaks Resort](https://www.expedia.ca/Lake-Placid-Hotels-High-Peaks-Resort.h2163041.Hotel-Information) > > [The Whiteface Lodge](https://www.expedia.ca/Lake-Placid-Hotels-The-Whiteface-Lodge.h1343777.Hotel-Information) > > [Days Inn by Wyndham Plattsburgh](https://www.expedia.ca/Plattsburgh-Hotels-Days-Inn-By-Wyndham-Plattsburgh.h40554.Hotel-Information) > > [Holiday Inn Express Hotel & Suites Niagara Falls by IHG](https://www.expedia.ca/Niagara-Falls-Hotels-Holiday-Inn-Express-Hotel-Suites-Niagara-Falls.h1946351.Hotel-Information) > > [Comfort Inn & Suites Watertown - 1000 Islands](https://www.expedia.ca/Watertown-Hotels-Comfort-Inn-Suites-Watertown-1000-Islands.h8037.Hotel-Information) > > [Niagara Crossing Hotel & Spa](https://www.expedia.ca/Niagara-Falls-Hotels-Niagara-Crossing-Hotel-Spa.h11603917.Hotel-Information) > > [Darien Lake Lodge on the Lake](https://www.expedia.ca/Corfu-Hotels-Darien-Lake-Lodge-On-The-Lake.h13279584.Hotel-Information) > > [Bluff Point Golf Resort](https://www.expedia.ca/Plattsburgh-Hotels-Bluff-Point-Golf-Resort.h16037595.Hotel-Information) > > [The Brook at Turning Stone Resort Casino](https://www.expedia.ca/Utica-Hotels-Turning-Stone-Resort-And-Casino.h1684407.Hotel-Information) > > [Best Western Plus Plattsburgh](https://www.expedia.ca/Plattsburgh-Hotels-Best-Western-Plus-Plattsburgh.h3120.Hotel-Information) > > [The Inn At Holiday Valley](https://www.expedia.ca/Ellicottville-Hotels-The-Inn-At-Holiday-Valley.h2184187.Hotel-Information) > > [Comfort Inn & Suites Plattsburgh - Morrisonville](https://www.expedia.ca/Plattsburgh-Hotels-Comfort-Inn-Suites-Plattsburgh-Morrisonville.h18189.Hotel-Information) > > [del Lago Resort & Casino](https://www.expedia.ca/Waterloo-Hotels-Del-Lago-Resort-Casino.h18258309.Hotel-Information) > > [Comfort Inn & Suites Niagara Falls Blvd USA](https://www.expedia.ca/Niagara-Falls-Hotels-Comfort-Inn-Suites-Niagara-Falls-Blvd-USA.h20009524.Hotel-Information) > > [Holiday Inn Express Plattsburgh by IHG](https://www.expedia.ca/Plattsburgh-Hotels-Holiday-Inn-Express-Plattsburgh.h5588.Hotel-Information) > > [Hampton Inn Kingston](https://www.expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information)