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 Aug 21, 2025, prices found for a 1-night stay for 2 adults at Work and Play Special! Extended Stay Discount on Sept 14, 2025 start from CA $1,109.84, 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.

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

Yes, this property allows dogs (limit 1 total).

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. Havens House and Shelter Island Historical Society are also within 1 mi (2 km).

Work and Play Special! Extended Stay Discount - Latest Reviews, Deals & Photos 2025

10/10 Excellent

Karin W.

May 19, 2025

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

10/10 Excellent

Liz C.

Aug 20, 2024

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

10/10 Excellent

Zach J.

Oct 10, 2023

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

10/10 Excellent

Christina V.

Jun 22, 2023

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

10/10 Excellent

Tessa W.

Jun 1, 2023

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

10/10 Excellent

Naomi R.

Jun 25, 2024

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

10/10 Excellent

Tessa W.

Sep 13, 2023

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

10/10 Excellent

Jesse A.

Jun 29, 2023

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

10/10 Excellent

M W.

Jun 26, 2023

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

10/10 Excellent

Aron H.

Jun 13, 2024

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

10/10 Excellent

Aura Z.

Oct 3, 2020

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

10/10 Excellent

Rachel R.

Sep 11, 2024

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

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

Evamarie D.

Aug 5, 2023

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

10/10 Excellent

martha k.

Jul 7, 2024

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

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

Joe B., Princeton, NJ

Jul 9, 2023

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

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

jill N.

May 28, 2024

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

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

LYNDA Z.

Sep 29, 2023

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

10/10 Excellent

Nicole M.

May 10, 2023

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

10/10 Excellent

Marcos C.

Oct 12, 2022

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

Paradise

My friends and family had a wonderful time staying at Ingrid’s place. We lounged by the pool, tossed a football in the backyard, and roasted marshmallows in the fire at night. The house is welcoming and cozy, and just a short drive away from Shelter Island’s many shops, beaches, or the ferry. I couldn’t recommend this place enough.

Stayed 2 nights in Oct 2022

10/10 Excellent

Linda a c., Rensselaer

Oct 5, 2022

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

Excellent, always

We are repeat customers. Love the location, the pool is awesome, and owners are cooperative and easy to deal with. They readily worked with us when a family death caused a change in dates and plans. I would definitely recommend it!

Stayed 8 nights in Sep 2022

10/10 Excellent

Katherine A.

Sep 22, 2022

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

Perfect weekend getaway!

Loved this home! Would definitely stay again. The house is adorable, clean and comfortable. The pool was incredible and the outdoor activities provided were endless! Visited for the weekend for a friends wedding and I was very happy with this lovely home!

Stayed 2 nights in Sep 2022

10/10 Excellent

Michael W.

Sep 20, 2022

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

Great cottage getaway

Fantastic host and great property to have a fun weekend with friends and family

Stayed 3 nights in Sep 2022

10/10 Excellent

Lori T., Montclair, NJ

Aug 9, 2022

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

Lovely Cottage with Pool

This property was perfect for our family of 6. The kitchen was well equipped and we really enjoyed the beautiful pool and 15 minute walk to the beach.

Stayed 7 nights in Jul 2022

10/10 Excellent

Patrick K.

Aug 5, 2022

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

Tiny cottage with beautiful pool & property

My family very much enjoyed our stay at Cottage Green. The kitchen, pool and expansive property are highlights! The hosts were excellent - responsive, lovely in person and very accommodating. The cottage has a well appointed kitchen, plenty of towels, washer dryer and room by room A/C. Wifi was consistent. It is a 12-15 min walk to Wades Beach (4 min drive) and a 2 min drive to South Ferry. The driveway holds plenty of cars but is completely blind (treacherous) trying to turn onto S Ferry Road. The cottage is tiny with only one bathroom in the main house - but there is a second half bath in the pool house + an outdoor shower. The two upstairs bedroom are suitable for children - as they are accessed by ladder - not stairs. The two main floor bedrooms are very tiny but adequate. Beds could use some upgrading. Overall, excellent choice for a small family's vacation on lovely Shelter Island.

Stayed 7 nights in Jul 2022

10/10 Excellent

tawana s.

Jul 30, 2022

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

Phenomenal!! will be back for sure!!

Loved absolutely everything. the description is totally accurate and the house and grounds exceeded our expectations!

Stayed 7 nights in Jul 2022

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