Entire home

Work and Play Special! Extended Stay Discount

Vacation home in Shelter Island with private pool and kitchen

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Photo gallery for Work and Play Special! Extended Stay Discount

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

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms1 bathroomSleeps 10

Popular amenities

  • Dryer
  • Washer
  • Pet friendly
  • Parking available

Explore the area

View in a map
Shelter Island, NY
  • Place, Wades Beach
    ‪14 min walk‬
  • Place, Mashomack Preserve
    ‪3 min drive‬
  • Place, Sunset Beach
    ‪8 min drive‬
  • Airport, New London, CT (GON-Groton - New London)
    ‪168 min drive‬

Room options

About the neighborhood

Shelter Island

Within a short walk of Wades Beach, this vacation home is within a mile (2 km) of Havens House. The vacation home includes a private pool, a kitchen, and a patio.

What's nearby

  • Wades Beach - 14 min walk - 0.8 miles
  • Mashomack Preserve - 3 min drive - 1.6 miles
  • Gardiner's Bay Country Club - 7 min drive - 3.7 miles
  • Sunset Beach - 8 min drive - 3.8 miles
  • Sag Harbor Marine Park - 15 min drive - 4.5 miles

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 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!!
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 5 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a coffee maker. Housekeeping is available on request.

Similar properties

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)

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

  • This property welcomes pets
  • Dogs only
  • 1 total pets
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 27

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a smoke detector, and a first aid kit.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.

Property is also known as

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

Frequently asked questions

What is there to do around this vacation home?

This vacation home is located in Shelter Island, a short 15-minute walk from Wades Beach and also 20 minutes on foot from Havens House. You'll also find Sunset Beach and Sag Harbor Marine Park within a short drive.

How much does it cost to stay at Work and Play Special! Extended Stay Discount ?

As of Oct 17, 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 $800.0, 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 for more accurate prices.

Will I be able to park at this vacation home?

No, there isn't parking available at the vacation home.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is an outdoor pool.

Is Work and Play Special! Extended Stay Discount a good place to stay for couples?

This historic vacation home offers many amenities for couples such as a private pool, private pools in some accommodations, as well as an outdoor pool.

Are there hot tubs at Work and Play Special! Extended Stay Discount ?

No, but this vacation home does have a heated pool.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is East Hampton, NY (HTO), which is 8.9 mi away (37 minutes by car). Another top airport is Montauk, NY (MTP), which is located 30 mi away (74-minute drive).

Can I book a room with a balcony at Work and Play Special! Extended Stay Discount ?

Yes, every accommodation at Work and Play Special! Extended Stay Discount comes with a deck.