Entire home

Work and Play Special! Extended Stay Discount

Photo gallery for Work and Play Special! Extended Stay Discount

A gravel path leading through a grassy area with trees and a stone wall in the background.
A two-story house with a covered porch, a flag, and well-maintained landscaping.
A grey wooden shed with a sliding door, located next to a house with a window.
A modern bathroom with a large arched window, a white bathtub, a white chair, and a bed.
A hotel room with a large bed, a mirror, and a painting of a woman by the sea.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Private pool
  • Kitchenette
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning

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, Westhampton, NY (FOK-Francis S. Gabreski)
    ‪57 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed

Bedroom 3: Upstairs bedroom

2 Single Beds

Bedroom 4: Upstairs bedroom

1 King Bed

Pool house

1 King Bed

2 bathrooms, 1 half bathroom

main floor full bathroom

Bathtub or shower · Toilet · Outdoor shower

Outdoor shower

Outdoor shower

Pool house

Toilet

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Kitchenette
Outdoor play area
Garden

Add dates for prices

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About the area

Shelter Island

Located in Shelter Island, this holiday home is near the beach. Shelter Island Whale's Tail and Gardiner's Bay Country Club are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Bay Street Theatre and Sag Harbor Whaling and Historical Museum. East End Seaport Maritime Museum and Greenport Carousel are also worth visiting. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
View more Holiday homes in Shelter IslandOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Wades Beach - 1 min drive - 1.5 km
  • The Hamptons Beaches - 8 min drive - 1.6 km
  • Wolffer Estates Vineyard - 24 min drive - 16.6 km
  • East Hampton Main Beach - 30 min drive - 23.3 km
  • Cooper's Beach - 44 min drive - 34.1 km

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
  • ‪Pridwin Hotel - ‬8 min drive
  • ‪Sunset Beach Restaurant - ‬7 min drive
  • ‪K Pasa - ‬13 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.

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

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

How much is parking at Work and Play Special! Extended Stay Discount ?

On-site parking is available at the property.

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 mi (2 km) of Wades Beach and The Hamptons Beaches. Havens House and Shelter Island Historical Society are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 59 out of 62 reviews
Rating 8 - Good. 3 out of 62 reviews
Rating 6 - Okay. 0 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 0 out of 62 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Suited our needs just fine. Was a little smaller than we needed, but had everything we needed to be comfortable. Host was quick to respond to our needs during our stay. Price was on point to other properties on shelter island. Location to south ferry a plus.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed here for a family wedding on the island, and the location was perfect—close to the venue and easy to get to. Check-in was simple, and communication with the owner was excellent. The house was very clean, and the kitchen was well-equipped with everything we needed. The property is beautiful and tucked away off the road, making it feel peaceful and private. We would definitely stay here again and highly recommend it!
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was as advertised.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower
Stayed 2 nights in Jun 2026
Response from VrboOwner on 7 Jun 2026
Thank you so much! We hope that you will come again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ingrid and Bobby’s home is like a little magical oasis. You’re surrounded by natural beauty with deer wondering about and a pond filled with little turtles. The beds are so comfortable! Better than a hotel! The home looks small on the outside but there’s more than enough room on the inside with lots of different areas to hang inside and out. We stayed there with our three children and they spent hours and hours in the salt water pool. They have speakers all around that you can connect to. Ingrid responded to every message immediately and check in was seamless. Highly recommend! We hope to come back next year
Stayed 4 nights in Aug 2026
Response from VrboOwner on 13 Aug 2026
Thank you so much for your wonderful words! We hope to welcome you again soonm
Verified review

10/10 Excellent

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
Response from VrboOwner on 30 Jul 2025
Thank you for choosing our home for your vacation! We hope that you will come back again soon!
Verified review

10/10 Excellent

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
Response from VrboOwner on 7 Dec 2025
Thank you so much! We will welcome you back!
Verified review

10/10 Excellent

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

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

10/10 Excellent

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
Response from VrboOwner on 15 Aug 2025
Thank you so much for staying with us!
Verified review

10/10 Excellent

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
Response from VrboOwner on 26 Jul 2025
Thank you for choosing our cottage! We hope that you will come visit us again!
Verified review

10/10 Excellent

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
Response from VrboOwner on 30 Jul 2025
Thank you so much! We hope that you will come back soon!
Verified review

10/10 Excellent

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
Response from VrboOwner on 2 Sept 2025
Thank you so much!
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 7 Dec 2025
Thank you so much! We hope that you will come back and stay with us!
Verified review

10/10 Excellent

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
Response from VrboOwner on 26 Jul 2025
Thank you so much for your resent stay! I hope to welcome you back soon!
Verified review

10/10 Excellent

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

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

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
Response from VrboOwner on 20 Sept 2023
Thank you so much!
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 16 Apr 2024
Thank you so much! We cant wait to welcome you back!
Verified review

10/10 Excellent

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

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

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
Response from VrboOwner on 20 Sept 2023
They were wonderful guests!
Verified review

10/10 Excellent

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
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