House in Shelter Island, NY
8 guests · 5 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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
-- 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
Amenities at Shelter Island Retreat w/ Outdoor Pool!
Non-smoking
No pets allowed
Family friendly
Map of Shelter Island, NY
Ratings and reviews
10 / 10Outstanding·Sep 2025
Wonderful home in a gorgeous location.
10 / 10Outstanding·Jun 2025
Lovely house with great accommodations. Any questions we had were quickly answered. Perfect location - beautiful views from the decks. Look forward to returning!
10 / 10Outstanding·Oct 2024
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.
10 / 10Outstanding·Sep 2024
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.
$$$$
Top rated by guests
10Outstanding
(5 Ratings)
"Wonderful home in a gorgeous location. "
craig h.Don't miss out! Price and availability may change
