Vacation Home Rentals By Owner In Shelter Island, NY

Exceptional(52)

$472.87
/ Nightly

Private Vacation Home

Peaceful and Private Shelter Island Getaway

Shelter Island, New York, United States
Enjoy a charming 3 bedroom/2 bath with central AC on an expansive shy acre corner plot located directly across from Sylvester Manor Farm. The land across the street is a preserve and the adjacent lot is undeveloped which allows for plenty of relaxation and privacy. An 800 sqft (open plan) great room with two balconies and large windows is perfect for entertaining or lounging with a good book. The rear balcony descends to a gravel patio area with a fire pit, dining area and charcoal BBQ grill. Owners are very reasonable, responsive, and pet friendly! brbrAbout the Area: Shelter Island is unique to Long Island's east end because it's only accessible by ferry. Upon arriving in S.I., you truly feel like you are in a different world with vacation mode fully setting in. You may be happy to hear that the island has been dubbed the un Hamptons by some because of its low key, relaxed and quiet atmosphere. Shelter Island is home to the 2,100 acre Mashomack Preserve which contains about 10 miles of coastline and represents 1/3 of the island. There you find breathtaking views of fields, creeks, and shoreline. If you are in the mood for an adventure, hop on the north ferry towards Greenport or the south ferry towards Sag Harbor and The Hamptons.brbr Additional notable amenities:brbr -Queen sized air mattress brbr -Workstation with WIFI and a new printer/scannerbrbr -New 55 smart TV with Netflix etc. brbr -Charcoal BBQ grillbrbr-Hammockbrbr -12 cup coffee machinebrbr -New washer/dryerbrbr -Working fireplacebrbr -Outdoor patio setbrbr -Walking distance to mini golfbrbr -Located close to marina & beaches.brbr

3
Bed

2
Bath

5
Sleeps

Exceptional(28)

$805.85
/ Nightly

Private Vacation Home

Private wooded summer house 5 minute walk to Wades Beach

Shelter Island, New York, United States
Privately located on a wooded hill near Wades Beach (5 minute walk) and Fresh Pond (1 minute walk). Open concept floor plan. Clean lines and modern furniture. Chef's kitchen with Viking appliances.brbrSpacious deck off the living room perfect for lounging and cocktails and a second deck off the kitchen with outdoor grill.brbr55 in. TV in living room and 40 in. TV in master–both with cable. High-speed WiFi + Sonos sound system.brbrBeach chairs, towels and gear provided.brbrA 5 minute boat ride on South Ferry leads you to Sag Harbor and the Hamptons. A 10 minute boat ride on North Ferry takes you to Greenport and dozens of vineyards on the North Fork.

4
Bed

2
Bath

6
Sleeps

Exceptional(28)

$805.85
/ Nightly

Private Vacation Home

Private wooded summer house 5 minute walk to Wades Beach

Shelter Island, New York, United States
Privately located on a wooded hill near Wades Beach (5 minute walk) and Fresh Pond (1 minute walk). Open concept floor plan. Clean lines and modern furniture. Chef's kitchen with Viking appliances.brbrSpacious deck off the living room perfect for lounging and cocktails and a second deck off the kitchen with outdoor grill.brbr55 in. TV in living room and 40 in. TV in master–both with cable. High-speed WiFi + Sonos sound system.brbrBeach chairs, towels and gear provided.brbrA 5 minute boat ride on South Ferry leads you to Sag Harbor and the Hamptons. A 10 minute boat ride on North Ferry takes you to Greenport and dozens of vineyards on the North Fork.

4
Bed

2
Bath

6
Sleeps

Exceptional(28)

$924.17
/ Nightly

Private vacation home

Waterfront Estate on Shelter Island - 200 Feet of Waterfront - 100 Foot Dock

Shelter Island, New York, United States

4
Bed

3
Bath

8
Sleeps

Exceptional(28)

$759.77
/ Nightly

Private vacation home

Beautiful, quiet, private, short walk to the beach.

Shelter Island, New York, United States

3
Bed

2
Bath

6
Sleeps

Exceptional(28)

$805.85
/ Nightly

Private vacation home

Private wooded summer house 5 minute walk to Wades Beach

Shelter Island, New York, United States

4
Bed

2
Bath

6
Sleeps

Exceptional(28)

$847.02
/ Nightly

Private vacation home

Shelter Island Retreat, 5 bdrms near everything!

Shelter Island, New York, United States

5
Bed

2
Bath

8
Sleeps

Exceptional(28)

$855.50
/ Nightly

Private vacation home

Lovely home by the sea with dock and heated Gunite pool!

Shelter Island, New York, United States

4
Bed

3
Bath

10
Sleeps

Exceptional(28)

$877.28
/ Nightly

Private vacation home

Shelter Island Sun Filled Modern Waterfront Home with Dock

Shelter Island, New York, United States

3
Bed

4
Bath

6
Sleeps

Exceptional(28)

$1013.36
/ Nightly

Private vacation home

Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly

Shelter Island, New York, United States

3
Bed

2
Bath

9
Sleeps

Exceptional(28)

$1056.81
/ Nightly

Private vacation home

Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12

Shelter Island, New York, United States

6
Bed

3
Bath

12
Sleeps

Exceptional(28)

$1013.95
/ Nightly

Private vacation home

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island, New York, United States

3
Bed

2
Bath

6
Sleeps

Exceptional(28)

$752.47
/ Nightly

Cottage

Charming, Historic Cottage

Shelter Island, New York, United States

3
Bed

2
Bath

6
Sleeps