
Holiday rentals in Shelter Island Heights
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Shelter Island Heights
Guests agree: these stays are highly rated for location, cleanliness and more.

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

Waterfront NoFo Cottage w/ public beach access
Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

Serene East Hampton Escape - Stars Forest Sauna
A luxuriously curated woodland escape with massive pool, outdoor dining living and play areas, fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with a french privacy door, a freestanding soaking tub, and a chef’s kitchen with dining table for ten or more.

The Hideaway | Clearwater Beach
Your private retreat in the heart of Clearwater Beach, East Hampton! Escape to this serene, design-forward suite nestled in one of the most peaceful corners of the Hamptons. Just minutes from the bay, this luxury hideaway offers the perfect balance of comfort, style and convenience. The space features a plush king bed and all the amenities you need for a relaxing stay. Sip your morning coffee in your private outdoor space before heading off for a swim at Clearwater Beach.

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

J&J's BnB Lovely, BR/Bath w/ Private Entrance!
Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

Hamptons - Shelter Island Farmhouse
Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Astounding Watermill 5 Bedroom home with Pool
Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Lovely 2-bedroom apartment in a historic home
Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Walk to Vineyards, Beaches, Farms & Town
Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Private Suite in a Greenport Historical Townhouse
Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.

4 BD w/ Heated Pool in E Hampton, Fully Furnished
Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.
Popular amenities for Shelter Island Heights holiday rentals
Other great holiday rentals in Shelter Island Heights

Waterfront Treehouse with Pool as seen on HBO

Peaceful and Private 3 bedroom home in the woods

Designer Renovated Farmhouse with Pool

Shelter Island Waterfront Getaway

Casa Greenport

Stylish Studio Suite on Shelter Island

Moonlit Manor | Shelter Island Escape w/ Sauna

3 Min Walk to Beach|Close to Town| Fam-Friendly
When is the best time to visit Shelter Island Heights?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £259 | £268 | £277 | £278 | £333 | £380 | £439 | £445 | £373 | £318 | £285 | £268 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
Are there Shelter Island Heights vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 150 vacation homes with pools in Shelter Island Heights, available on Airbnb. Make a splash and soak up the sun in style!
Do bed and breakfast rentals in Shelter Island Heights have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Shelter Island Heights?
Shelter Island Heights has more than 350 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Shelter Island Heights?
Yes! Work meets play with ease at over 220 vacation rentals in Shelter Island Heights featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Shelter Island Heights?
Experience the best of Shelter Island Heights with our apartment rentals, starting at about $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Shelter Island Heights have free parking?
Absolutely! We offer over 280 house rentals with free parking in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Bed And Breakfast Rentals in Shelter Island Heights?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shelter Island Heights have a kitchen?
Absolutely! We offer over 280 house rentals with a kitchen in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Shelter Island Heights have wifi?
Absolutely! We offer over 20 condo rentals with wifi in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Shelter Island Heights?
Four-legged friends are welcome in Shelter Island Heights. Choose from more than 140 vacation rentals for guests traveling with pets.
Quick stats about holiday rentals in Shelter Island Heights

Total holiday rentals
Explore 430 holiday rentals in Shelter Island Heights

Nightly prices starting at
Shelter Island Heights holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 16,450 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Holiday rentals with a pool
160 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
410 of Shelter Island Heights holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelter Island Heights rentals

4.9 Average rating
Shelter Island Heights stays are highly rated by guests – averaging 4.9 out of 5!
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