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Work and Play Special! Extended Stay Discount

Holiday home in Shelter Island with private pool and kitchen

Photo gallery for Work and Play Special! Extended Stay Discount

Fridge, microwave, oven, stovetop
5 bedrooms, in-room safe, desk, free WiFi
Smart TV, ping pong, stereo
Fridge, microwave, oven, stovetop
Outdoor pool, a heated pool

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms1 bathroomSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View map
Shelter Island, NY
  • Place, Wades Beach
    ‪14 min walk‬
  • Place, Mashomack Preserve
    ‪3 min drive‬
  • Place, The Hamptons Beaches
    ‪8 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪52 min drive‬

Room options

About the area

Shelter Island

At this holiday home you'll be within a 20-minute stroll of Wades Beach and Havens House. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, a patio and a living room. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A Smart TV, a coffee/tea maker and a safe are also available. Housekeeping is available on request. .This pet-friendly holiday home offers an outdoor pool, a garden and barbecues. Additionally, you'll find laundry facilities. .Sights within a 30-minute walk of this Shelter Island holiday home include Shelter Island Historical Society and Mashomack Preserve.
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What's nearby

  • Wades Beach - 14 min walk - 1.2 km
  • Shelter Island Historical Society - 2 min drive - 2.2 km
  • Havens House - 2 min drive - 2.2 km
  • Mashomack Preserve - 3 min drive - 2.5 km
  • The Hamptons Beaches - 8 min drive - 1.6 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
  • ‪Opties & Dinghies - ‬4 min drive
  • ‪Pridwin Hotel - ‬8 min drive
  • ‪Dock House - ‬14 min drive

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 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!!

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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 transport

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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

  • No lift
  • Smoke-free property

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
  • Fire extinguisher

General

  • Garden
  • Housekeeping (on request)

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 27

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Absolutely no parties or events of any kind.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 pets
    • Service animals are exempt from fees.

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
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all accommodation.

Property is also known as

Vrbo Property
Private Hamptons Cottage
Private Hamptons Cottage with excellent WiFi! Shelter Island

Frequently asked questions

Are there any beaches close to Work and Play Special! Extended Stay Discount ?

Yep, Work and Play Special! Extended Stay Discount is a short 15-minute walk from Wades Beach. Fun beach activities include kayaking, sailing and fishing. You can also find motor boats.

Does Work and Play Special! Extended Stay Discount have a pool?

Work and Play Special! Extended Stay Discount has a heated pool and a pool.

What luxury perks are available at Work and Play Special! Extended Stay Discount ?

This property features a heated pool, as well as a private pool and a living room.

Is Work and Play Special! Extended Stay Discount family-friendly?

You bet! With amenities such as a playground, laundry facilities and children's dinnerware, it's no surprise that Work and Play Special! Extended Stay Discount is a winner with our family travellers.

Is there a private hot tub at Work and Play Special! Extended Stay Discount ?

No, but there is a private pool.

Is there a free airport shuttle available at Work and Play Special! Extended Stay Discount ?

No, Work and Play Special! Extended Stay Discount does not offer an airport shuttle service.

What time are check-in & check-out at Work and Play Special! Extended Stay Discount ?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Work and Play Special! Extended Stay Discount Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 51 out of 53 reviews
Rating 8 - Good. 2 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 0 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Adam M.

Liked: Cleanliness
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.
Stayed 4 nights in Nov 2025

10/10 Excellent

Hank P.

Liked: Cleanliness
Clean convenient
Stayed 1 night in Sep 2025

10/10 Excellent

Tracy S.

Liked: Cleanliness
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.
Stayed 3 nights in Sep 2025

10/10 Excellent

Anjelica B.

Liked: Cleanliness
Peaceful stay. Great pool. My kids and I liked walking to the beach from here.
Stayed 3 nights in Aug 2025

10/10 Excellent

C M.

Liked: Cleanliness
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.
Stayed 13 nights in Jul 2025

10/10 Excellent

Tessa W.

Liked: Cleanliness
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.
Stayed 3 nights in Jul 2025

10/10 Excellent

Joe B., Princeton, NJ

Liked: Cleanliness

Great, relaxing, peaceful home

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.
Stayed 4 nights in Jul 2025

10/10 Excellent

Nava S.

Liked: Cleanliness

A lovely weekend stay

Really great property, had a relaxing lovely time!
Stayed 2 nights in Jul 2025

10/10 Excellent

moshe A.

Liked: Cleanliness
The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now!
Stayed 2 nights in Jul 2025

10/10 Excellent

Tyler W.

Liked: Cleanliness

Wonderful Outdoor Space

Beautiful pool, badminton net, lots of outdoor seating areas. Location is easy, very close to ferry and nature preserve.
Stayed 4 nights in Jul 2025

10/10 Excellent

Lily A.

Liked: Cleanliness

Great stay!

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.
Stayed 2 nights in Jun 2025

10/10 Excellent

Karin W.

Liked: Cleanliness

The 2 forks wine/bike trip

we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk
Stayed 1 night in May 2025

10/10 Excellent

Rachel R.

Liked: Cleanliness

A very special shelter island retreat

This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time.
Stayed 8 nights in Aug 2024

10/10 Excellent

Liz C.

Liked: Cleanliness

Beautiful Cozy Cottage

We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!
Stayed 7 nights in Aug 2024

10/10 Excellent

martha k.

Liked: Cleanliness

wedding week

The property is enormous and gracious; the house is a perfect size for our needs and has a lot of charm. But it is the huge pool, the eating and sitting areas, and beauty of the rolling nature there that sets this property apart from others I have seen. What other houses might have in capaciousness, they lack in generous surroundings. Ingrid was superbly accommodating and an adept communicator. The week was a dream. A+
Stayed 5 nights in Jun 2024

10/10 Excellent

Naomi R.

Liked: Cleanliness

Will be back!

Ingrid was incredibly communicative throughout and ensured the space was clean. What a lovely well decorated home!
Stayed 2 nights in Jun 2024

10/10 Excellent

Aron H.

Liked: Cleanliness

Amazing Property

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!
Stayed 2 nights in Jun 2024

10/10 Excellent

jill N.

Liked: Cleanliness

Wonderful Stay

Ingrid’s house is magical. We stayed here for 4 days and had everything we needed. The pool was glorious. Sitting by the pond with the bullfrogs and turtles while listening to the multitudes of bird sounds was serene. Our kids playing badminton and ping pong, taking a respite from their swimming was perfect. This house and its garden, with spectacular trees was magical in every way. We felt truly lucky to have found this oasis. And the short walk to the beach another wonderful bonus. We had everything and thank Ingrid and Bobby for their hospitality. A definite must for us to revisit.
Stayed 3 nights in May 2024

10/10 Excellent

Zach J.

Liked: Cleanliness

Awesome, Quirky Shelter Island Home

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!
Stayed 2 nights in Sep 2023

10/10 Excellent

LYNDA Z.

Liked: Cleanliness

Wash Away Wedding

Lovely, well-equipped cottage. A quick, personal response from hosts to resolve an early morning question.
Stayed 2 nights in Sep 2023

10/10 Excellent

Tessa W.

Liked: Cleanliness

Beautiful property

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.
Stayed 2 nights in Sep 2023

10/10 Excellent

Evamarie D.

Liked: Cleanliness

The most relaxing weekend getaway!!

Ingrid and her place was just amazing!!! My family and I do a yearly vacation and this was our first time visiting Shelter Island. The property was three minutes from the south ferry, which was super convenient. The grounds were extremely spacious filled with wild life and nature!! The pool was just perfect!! The house was able to fit all 10 of us with myself and my husband staying in the very cute and private pool house which is separate from the main house. Highly recommend staying at this property! Looking forward to booking this place again in the future!!
Stayed 3 nights in Jul 2023

10/10 Excellent

Joe B., Princeton, NJ

Liked: Cleanliness

The property is beautiful and the salt-water pool fantastic

Ingrid was very helpful and accommodating. The property is beautiful and the salt-water pool fantastic. Our 2-year-old grandson finally learned to enjoy going into the water after spending a few days playing in the pool. Our daughter, who produces films, was thrilled to learn that her favorite film producer, Sam Green, has spent a lot of time at the property, especially when he was younger. One thing to be aware of is that the 2 upstairs bathrooms are reached via very steep stairs which some may find difficult to climb and descend. And, there is no bathroom upstairs. Wades Beach is a relatively easy walk; however, we needed a car for most other outings. Since we had only 1 car, we occasionally tried to use uber or taxi service and found both to be unreliable. We were there just before the July 4th peak. Possibly better service is provided during the peak summer season. The Welcome book/instructions could have been more complete; however, Ingrid’s helpfulness and availability compensated for that. The VRBO app and website was difficult and time consuming to use once we made the reservation; e.g., there were times when we could not see recent messages from Ingrid and it would do things like indicate that we had no messages even just after notifying us that there was a new message!
Stayed 4 nights in Jun 2023

10/10 Excellent

Jesse A.

Liked: Cleanliness

Relaxing

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
Stayed 3 nights in Jun 2023

10/10 Excellent

M W.

Liked: Cleanliness

Amazing!

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!
Stayed 4 nights in Jun 2023