Entire home

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

Property grounds
Outdoor pool, a heated pool
Dining
Fridge, microwave, oven, stovetop
5 bedrooms, in-room safe, desk, free WiFi
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.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms1 bathroomSleeps 10

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
The current price is AU$2,214
includes taxes & fees
5 Nov - 6 Nov

Add dates for prices

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 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

  • 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

General

  • Garden
  • Housekeeping (on request)

Similar properties

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

Rules

Absolutely no parties or events of any kind.

Pets

Pets are 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
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 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

Located in Shelter Island, this holiday home is near the beach. Shelter Island Whale's Tail and Shelter Island Country Club are worth checking out if an activity is on the agenda, while those looking for area attractions can visit BookHampton and Sag Harbor Whaling and Historical Museum. East End Seaport Maritime Museum and Greenport Carousel are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
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
  • ‪Opties & Dinghies - ‬4 min drive
  • ‪Pridwin Hotel - ‬8 min drive
  • ‪Dock House - ‬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 10 Oct 2025, prices found for a 1-night stay for 2 adults at Work and Play Special! Extended Stay Discount on 5 Nov 2025 start from AU$2,214.06, 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).

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 ?

Checkout is at 11:00 AM.

Where is Work and Play Special! Extended Stay Discount located?

Situated near the beach, this holiday home is within 1 mile (2 km) of Wades Beach, Havens House and Shelter Island Historical Society. Mashomack Preserve and Shelter Island Whale's Tail are also within 2 miles (3 km).

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