Top 1% of guest reviews in this areaTop 1% of guest reviews in this area
Highlights
Outdoor pool
The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
Centrally-located
You're never far from where you need to be with this convenient location.
5 bedrooms2+ bathroomsSleeps 10
Popular amenities
Private pool
Onsite parking available
Dog-friendly
Kitchen
Washer
Air conditioning
Explore the area
Shelter Island, NY
Wades Beach
Place, Wades Beach
1 min drive
The Hamptons Beaches
Place, The Hamptons Beaches
8 min drive
Cooper's Beach
Place, Cooper's Beach
44 min drive
East Hampton, NY (HTO)
Airport, East Hampton, NY (HTO)
24 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Double Bed
Bedroom 3: Upstairs bedroom
2 Twin Beds
Bedroom 4: Upstairs bedroom
1 King Bed
Pool house
1 King Bed
2 bathrooms, 1 half bathroom
main floor full bathroom
Bathtub or shower · Toilet · Outdoor shower
Outdoor shower
Outdoor shower
Pool house
Toilet
Spaces
Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Kitchenette
Outdoor play area
Garden
About this property
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 8 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!!
Our prices include all fees. No hidden fees.
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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 fire extinguisher and a first aid kit
About the neighborhood
Shelter Island
Located in Shelter Island, this vacation home is near the beach. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Shelter Island Whale's Tail and Bay Street Theatre are also worth visiting. Discover the area's water adventures with kayaking and motor boating nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
Shinnecock Hills Golf Course - 38 min drive - 30.3 km
Cooper's Beach - 44 min drive - 34.1 km
Getting around
Greenport Station - 26 min drive
East Hampton, NY (HTO) - 37 min drive
Restaurants
K Pasa - 13 min drive
Shelter Island Craft Brewery - 4 min drive
Corner Bar - 13 min drive
Le Bilboquet - 14 min drive
Grindstone Coffee & Donuts - 14 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 Jun 9, 2026, prices found for a 1-night stay for 2 adults at Work and Play Special! Extended Stay Discount on Sep 17, 2026 start from $1,566, including 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 for more accurate prices.
Is Work and Play Special! Extended Stay Discount pet-friendly?
Yes, this property allows dogs (limit 1 total).
How much is parking?
Onsite parking is available at the property.
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 and The Hamptons Beaches. Mashomack Preserve and Shelter Island Whale's Tail are also within 2 mi (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower
Kathleen Andrews K.
Stayed 2 nights in Jun 2026
Response from VrboOwner on Jun 7, 2026
Thank you so much! We hope that you will come again soon!
This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want.
We've booked this property multiple times and always had a wonderful time. The hosts are responsive and helpful and the house is always clean and put together. We will definitely be returning.
This cottage was a very nice place with spacious gardens and lovely pool to hang out by. Great location for our family as it was close to the wedding event and to town. All our needs were met. Thank you to the host.
Tracy S.
Stayed 3 nights in Sep 2025
Response from VrboOwner on Dec 7, 2025
Thank you so much! We hope that you will come back and stay with us!
The property was very beautiful. My family and I loved the pool, grounds, house and local wildlfe that visited. We had easy correspondence with the owner; they responded immediately and were very helpful.
The property was beautiful, and Ingrid was a great host! We were in town for a wedding and not within walking distance of dinner so Ingrid helped me set up transportation. The outdoor shower helped a lot in terms of helping us get ready on time, and it was great to have the whole pool area.
Lily A.
Stayed 2 nights in Jun 2025
Response from VrboOwner on Jul 26, 2025
Thank you so much for your resent stay! I hope to welcome you back soon!
Beautiful property, wish we could have stayed longer
Gorgeous property. The pool was fantastic. We stayed with friends in between a wedding weekends events and we kept saying we wish we could just spend more time at the house!!
This is the perfect house. The amenities were fantastic, the owners were easy to communicate with and welcoming. My whole group had a wonderful time and are already looking at future dates to come back!
We had an awesome time staying at Ingrid's place. She was incredibly helpful and communicative throughout the process. The place was very fun, quirky but still exactly as advertised and was a great weekend stay. Highly recommend staying here in the future!
It was our second time booking the property. We love this place and can’t wait to go back. The house has everything you would need and the property is sprawling and gorgeous.
Tessa W.
Stayed 2 nights in Sep 2023
Response from VrboOwner on Apr 16, 2024
Thank you so much! We cant wait to welcome you back!
Clean, easy to get to, and a great place to stay. Property was gorgeous and plenty of wildlife to see in the yard. Pool is perfect for a nice swim and little to no bugs at night in the back
This is our 2nd time staying here. It has a great vibe and is filled with light with awesome settings for outside dining. The pool is spectacular.Two shortcomings: 1) It would be a significant improvement if there was a shower in the pool cottage.2) It’s a shame that the stairs to the second floor are so steep. Not all can safely use them.
Joe B.
Stayed 4 nights in Jul 2025
Response from VrboOwner on Jul 30, 2025
Thank you for your recent stay! We hope that you will come back again soon!
This is our second year back and we enjoyed every moment! The house and grounds are so lovely. The house is clean and has everything you need. The pool is amazing! Can’t wait to go back!
We had an amazing time in our week long local vacation. Ingrid was always available when we had questions. The pool was perfect and exactly what we needed. The heating feature was key as our trip took place late in the summer. We would definitely love to go back!
Incredibly beautiful space that has everything you need for a vacation getaway. Amazing backyard with a pool, plenty of seating to relax and recreation areas for play. Great sound system for groups.
Ingrid was so nice and welcoming, communication with her was super easy throughout the whole process.
Can't recommend this place enough!
Aron H.
Stayed 2 nights in Jun 2024
Response from VrboOwner on Jun 13, 2024
Thank you so much for choosing our home for your mini vacation! We hope that you will come back again soon!
Perfect place to host a girls weekend in the Hamptons
Ingrid is a kind and communicative host, and the property itself is stunning. As soon as we got there, we wished we were staying for even longer. Don't be intimidated by the ferry ride - it's fast and efficient and 1000% worth it to be able to access this hidden gem. Thank you so much!