Shelter Island house rentals
We found 2,232 house rentals — enter your dates for availability
Explore Shelter Island house rentals
Gorgeous Shelter Island Retreat with Pool and Private Grounds
Sleeps 8 · 3 bedrooms · 3 bathrooms
Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Work and Play Special! Extended Stay Discount
Sleeps 10 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Waterfront House With Dock And Private Beach
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Private oasis with new baths and heated Gunite pool near Wades Beach
Sleeps 8 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Top rated house rentals - Shelter Island
Highly recommend
1010 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Excellent experience with home, location, and property owner
Jeffrey M.
Stayed June 2024
Magical oasis on Shelter island
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
We stayed at Edward and Tracy’s oasis in Shelter island for a month. Words cannot express the magic of this house and property. We created lifelong memories, taking advantage of the amazing view, lawn and dock.
We came during C-19 to shelter in place and escape NYC and there couldn’t have been a more perfect place with ample workstations, super fast wifi, a kitchen with all the gadgets for your at-home chef dreams and tranquility in the beautifully made up bedrooms that felt like you were in a boutique hotel! Edward and Tracy really made us feel safe, making sure we had ample supplies and ensuring the house was fully sanitized before we stayed.
There is so much to do at the property that you don't ever need to leave including swimming off the dock, lovely picnics on the lawn at sun set, grilling on the patio, taking a bath that overlooks the water and meditating on the dock. This was perfect for us to shelter in place in shelter island :) Although we never really needed to leave we do highly recommend the lobster and oysters from Commander Cody after going for hikes in the nature preserve a mile away…!
We couldn’t recommend their home more, we feel very grateful for Edward and Tracy opening up their house and they were an absolute pleasure in all of our communications and all. We cannot wait to go back. Thank you Edward and Tracy!
Negar A.
Stayed May 2020
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Frequently asked questions
Are there any holiday home rentals in Shelter Island?
Stay in one of our 2,232 holiday home rentals in Shelter Island and you'll have the ideal base for your next big adventure. Menantic Creek, Coecles Harbour and The Heights are among the city's most popular areas.
How much does it cost to stay in a holiday rental house in Shelter Island?
Your dream holiday home rental in Shelter Island is waiting to be discovered, with a range of prices from budget-friendly accommodation to more upscale options. Enter your travel dates to compare, ensuring you find the right place for you and your crew.
When is the best time to rent a holiday house in Shelter Island?
First, decide whether you prefer the bustle of high season or the quieter vibe of low season. Also think about things like seasonal weather conditions and what you'd like to see in Shelter Island. Whenever you go, there'll be a holiday home rental with your name on it.
Where can I rent a Shelter Island holiday house with great views?
There's only one thing better than enjoying a break in one of our Shelter Island holiday home rentals — staying someplace that comes with gorgeous views. Scroll through our options to discover a house with the amenities you need and the outlooks that'll make your getaway even more memorable. Sort your results by "Guest rating" or "Recommended" and see what's available.
Does Shelter Island have any weekend house rentals?
Some of our holiday houses are available for weekend rental, making them perfect for spontaneous getaways. Enter your desired travel dates to view the availability. You may need to play around with dates and have a little flexibility in your plans to find the right holiday home rental in Shelter Island.
Are there any pet-friendly house rentals in Shelter Island?
Embark on your next adventure with your four-legged friend at one of our 15 pet-friendly holiday home rentals in Shelter Island. These properties come with features that'll make your dog feel at home, such as a fenced-in yard to play in. Just check the "Pets allowed" filter to find a house that has space for every cherished member of your family.
What are the top things to do in Shelter Island?
East Hampton Main Beach, Orient Point County Park and 67 Steps Beach are terrific attractions that'll keep the whole crew occupied in Shelter Island. There's nothing like a getaway to bring everyone together, so check out our holiday home rentals in this exciting destination.
Why should I book my holiday rental house with Stayz?
We take the hassle out of finding your ideal holiday home rental. Use our filters to fine-tune your search by budget, property type, amenities and more. Whatever your preference, you'll always get the whole space for you and whoever you're adventuring with. Plus, our cancellation policies offer peace of mind should your plans change. You'll get a full refund if you cancel your booking within the timeframe specified by the property's cancellation policy.