If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and restorative stay. With fun activities year-round, you can kayak on the nearby ocean, sip on some wine at the Wölffer Estate Vineyard, witness stunning views from Montauk Point, catch a Polo match, or get your holiday shopping done in the Hamptons!
-- THE PROPERTY --
Seasonal Outdoor Pool | Fully Equipped Home Gym | Free WiFi (High Speed) | 110 Mi to NYC | 5,000 Sq Ft
Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Bunk Beds | Bedroom 5: Queen Bed | Bonus Room: King Bed
OUTDOOR LIVING: Private beach w/ wood-burning fire pit & beach chairs, kayaks (available spring/summer months), near ocean, walk to beaches, deck, gas grill + outdoor kitchen area, outdoor fireplace, fire pit, bicycles, boating, beach chairs, beach umbrella, trampoline INDOOR LIVING: 3 Smart TVs w/ cable, en-suite bathrooms, walk-in closet, laptop-friendly workspace, game room w/ pool table, gas fireplaces, dining areas, jetted bathtub, shower, books KITCHEN: Refrigerator, stove/oven, blender, toaster, cooking basics GENERAL: Central A/C + heating, complimentary toiletries, linens/towels, washers/dryers, hair dryer, hangers, beach towels, trash bags/paper towels FAQ: Steps required for entry, bedroom + bathroom on 1st floor, zero-entrance shower PARKING: Driveway (7 vehicles)
-- THE LOCATION --
THINGS TO SEE + DO: Sylvester Manor Educational Farm - farm stand + theatre + live music in summer months (4 miles), Shelter Island Historical Society (5 miles), Horton Point Lighthouse Nautical Museum (12 miles), The Hamptons (16 miles), Parrish Art Museum (18 miles), Long Island Aquarium (29 miles), Montauk Point Lighthouse Museum (37 miles) GET OUTSIDE: Lower Beach (1 mile), Upper Beach (3 miles), Coecles Harbor Marina & Boatyard (4 miles), Mashomack Preserve Entrance - walking trails (5 miles), 67 Steps Beach (8 miles), Sagg Main Beach - surfing, deep sea fishing, water sports (17 miles) WINE & DINE: Ram's Head Inn (0.9 miles), Marie Eiffel Market (5 miles), Vine Street Cafe (5 miles), Greenport Harbor Brewing Company (7 miles), Kontokosta Winery (8 miles), One Woman Winery Greenport (10 miles), The Old Field Vineyards (10 miles), Sparkling Pointe Vineyards & Winery (12 miles), Channing Daughters Winery (13 miles), Wölffer Estate Vineyard (14 miles) AIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: There are a few steps required for entry, but there is a bedroom and bathroom with a zero-entrance shower on the main floor - NOTE: The outdoor pool is open seasonally from May-September and the kayaks are only available in the spring and summer months
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Amenities
Pool
Kitchen
Washing machine
Dryer
Air conditioning
Gym
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Shelter Island
Located in Shelter Island, this holiday home is on the beach. The area's natural beauty can be seen at The Hamptons Beaches and Orient Beach State Park, while Havens House and East End Seaport Maritime Museum are cultural highlights. Shelter Island Whale's Tail and Greenport Carousel are also worth visiting. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting nearby.
Gardiner's Bay Country Club - 6 min drive - 6.7 km
Shelter Island Whale's Tail - 7 min drive - 7.4 km
Sylvester Manor - 8 min drive - 8.1 km
Shelter Island Historical Society - 9 min drive - 9.2 km
Getting around
Greenport Station - 29 min drive
East Hampton, NY (HTO) - 56 min drive
Restaurants
Greenport Harbor Brewing Company - 30 min drive
Shelter Island Craft Brewery - 9 min drive
Crazy Beans - 30 min drive
Claudios Clam Bar - 30 min drive
Pip’s Cafe & Provisions - 30 min drive
Frequently asked questions
Does Shelter Island Retreat w/ Outdoor Pool! have a pool?
Yes, this property has a pool.
How much does it cost to stay at Shelter Island Retreat w/ Outdoor Pool!?
As of 7 Apr 2026, prices found for a 1-night stay for 2 adults at Shelter Island Retreat w/ Outdoor Pool! on 10 Apr 2026 start from AU$1,274, 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 Shelter Island Retreat w/ Outdoor Pool! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Shelter Island Retreat w/ Outdoor Pool!?
On-site parking is available at the property.
What time is check-in at Shelter Island Retreat w/ Outdoor Pool!?
Check-in begins at 3:00 PM.
What time is check-out at Shelter Island Retreat w/ Outdoor Pool!?
Checkout is at 10:00 AM.
Where is Shelter Island Retreat w/ Outdoor Pool! located?
This Shelter Island holiday home is on the beach, 2 mi (3.2 km) from Menhadden Lane Beach, and within 6 mi (10 km) of Sunset Beach and Crescent Beach. Gardiner's Bay Country Club and Shelter Island Country Club are also within 6 miles (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Lovely house with great accommodations. Any questions we had were quickly answered. Perfect location - beautiful views from the decks. Look forward to returning!
My family and I had a wonderful stay at this gorgeous property. The pool is terrific, the view is amazing, and the layout was perfect for our large family so we could all have our own spaces and bathrooms. We loved it.
Lauren R.
Stayed 4 nights in Aug 2024
From a partner site
10/10 Excellent
kerry
6 July 2023
The perfect getaway
Though we loved our outings on and around Shelter Island, we would have been just as happy never leaving the property! Our group enjoyed lazy days by the pool and delicious meals cooked at home in the gorgeous kitchen. Ashley was super responsive throughout the weekend, ensuring we had everything we needed. We just checked out last week and are already looking for a week we can come back next year (and hopefully stay even longer).
kerry
From a partner site
10/10 Excellent
Sara
7 Oct 2024
Just Perfect
8 of us old college friends stayed here for 3 nights for our annual reunion. This property on Shelter Island provided everything we might need, and exceeded our expectations. The beds were comfortable. The showers were hot. There were ensuite bathrooms for each bedroom. The kitchen was large and had every utensil needed to cook and serve a group. The dining table accommodated everyone. The living room had a large sectional for relaxing. But the best part was the view, the patio, and the proximity to a gorgeous rocky beach. We sat around and admired the view of the ocean, played bocce (provided with the property), and walked on the beach. It was perfect.