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Work and Play Special! Extended Stay Discount

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A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.
A modern living room with a sectional sofa, a glass coffee table, and large windows offering a view of greenery outside.
A room with a blue-striped table, white curtains, a blue sofa, and a patterned rug.
A modern bathroom with a large arched window, a white bathtub, a white chair, and a bed.
A backyard with a swimming pool, lounge chairs, and umbrellas.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms1 bathroomSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Shelter Island, NY
  • Place, Wades Beach
    ‪1 min drive‬
  • Place, The Hamptons Beaches
    ‪8 min drive‬
  • Place, Cooper's Beach
    ‪44 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪62 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 The Hamptons Beaches. The vacation home includes a private pool, a kitchen, and a patio.
View more Vacation Homes in Shelter IslandOpens in a new window

What's nearby

  • Wades Beach - 1 min drive - 0.9 miles
  • The Hamptons Beaches - 8 min drive - 1.0 mile
  • Wolffer Estates Vineyard - 24 min drive - 10.3 miles
  • Pindar Vineyards - 40 min drive - 14.8 miles
  • Cooper's Beach - 44 min drive - 21.2 miles

Getting around

  • Greenport Station - 26 min drive
  • East Hampton, NY (HTO) - 37 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬27 min drive
  • ‪Tutto il Giorno - ‬14 min drive
  • ‪K Pasa - ‬13 min drive
  • ‪Pridwin Hotel - ‬8 min drive
  • ‪Claudios Clam Bar - ‬27 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!!
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.

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North Fork Resort
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  • Pool
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9.4 out of 10, Exceptional, 44 reviews
$598 nightly
The price is $683
Aug 10 - Aug 11
Total with taxes and fees
North Fork Resort

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

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 elevator
  • 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
  • Fire extinguisher

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
Information provided by the property may be translated using automated translation tools

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 fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • 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 fire extinguisher, a smoke detector, and a first aid kit.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.
  • There are no elevators.

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 Shelter Island Historical Society. You'll also find The Hamptons Beaches and Sunset Beach within a short drive.

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

As of Aug 4, 2026, prices found for a 1-night stay for 2 adults at Work and Play Special! Extended Stay Discount on Aug 16, 2026 start from $1,918, 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 parking available on site at Work and Play Special! Extended Stay Discount ?

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 good for couples?

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

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

No, but guests can enjoy a heated pool at this vacation home.

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.

Are there connecting rooms at Work and Play Special! Extended Stay Discount ?

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).

Are there rooms with balconies that I can book at Work and Play Special! Extended Stay Discount ?

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

Work and Play Special! Extended Stay Discount Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 53 out of 55 reviews
Rating 8 - Good. 2 out of 55 reviews
Rating 6 - Okay. 0 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 0 out of 55 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Nava S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A lovely weekend stay

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

10/10 Excellent

Adam M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

Anjelica B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful stay. Great pool. My kids and I liked walking to the beach from here.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Hank P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean convenient
Stayed 1 night in Sep 2025
Verified review

10/10 Excellent

Tessa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

Tyler W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

moshe A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

C M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

Tracy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

Karin W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Lily A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liz C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Christina V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Tessa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Shelter Island Stay

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!
Stayed 2 nights in May 2023
Verified review

10/10 Excellent

Zach J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Tessa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Jesse A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

M W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Aura Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

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!
Stayed 7 nights in Sep 2020
Verified review

10/10 Excellent

Naomi R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Joe B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Aron H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Nicole M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 2 nights in May 2023
Verified review

10/10 Excellent

LYNDA Z.

Liked: Cleanliness, check-in, communication, location

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
Verified review

10/10 Excellent

Evamarie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

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