Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Cottages
Estates
Farmhouses
Hotels
Homes
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Shelter Island Pet Friendly Vacation Rentals(38)

38 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
(9)
3 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
14 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
6 - 28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(7)
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 - 31 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
14 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
(5)
1 - 5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 Review
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 7 night minimum stay
  • 3 BR,
  • Sleeps 5
$1,700
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
11 - 41 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night minimum stay
  • 3 BR,
  • Sleeps 8
2 Reviews
2 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 15
2 Reviews
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(9)
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
(6)
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
(5)
7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
(4)
7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
(3)
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
14 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
2 Reviews
Advertisement
 

Recent Shelter Island Reviews

Recommend!

5 of 5
We stayed here with a group of friends and family to relax before my sister's wedding. From the outside, it looks like a historical Victorian home, but from the inside everything is completely up to date and decorated tastefully, even a bit trendy. There are plenty of areas to lounge, but we spent most of our time on the front porch facing the water and doing a little people watching. One of the best features of the house is the location. You can walk to the beach, restaurants, the North ferry, etc. I would stay here again next summer.
  • Submitted: Aug 26, 2014
  • Stayed: Aug 2014

Stunning, fabulous location, GREAT HOUSE

5 of 5
What can I say except I am VERY picky when it comes to rental homes and this property is even better in person than any picture would do it justice, and it hands down beat my high expectations. Each room has been decorated in stunning furnishings, lighting, the right balance of classic and modern. The screened in porch was a great place to start the day with coffee and baked goods purchased on the island, and NOTHING beats getting on the ferry for the short crossing, its like all the stress goes away. I will for sure be renting this property again!
  • Submitted: May 6, 2014
  • Stayed: May 2014

Sweetest House, Kindest Landlady

5 of 5
This was a wonderful experience. I recommend this house to anyone who loves charm, history, and wonderful cozy casual chic. Everything was as represented on the website. Adorable house well located in the "center" of sleepy Shelter Island. The porch overlooks a park and the harbor. The old fashioned pharmacy across the street, was great for supplies, the morning paper, and a counter lunch or breakfast. A charming inn is across the road as well which was good for lunches and dinners with a view of the harbor. Also walking distance on the other side of the park there's another settlement with restaurants and shops. My landlady is the most considerate person I've ever encountered. On my arrival she had laid the table, stocked the fridge with salmon and chowder and desserts. The bedrooms are all charming and comfortable. The living room/dining room area is as comfortable as can be. The landlady anticipates one's every need and goes beyond the beyond to make her tenants happy. If you are looking for a pretty island away from the sometimes frantic Hamptons scene, you will love this. Tennis and golf are nearby. Swimming can be had at the sweet little beach club down by the ferry landing. I recommend bringing a car to explore some the islands other charms, and to breeze quickly across on the ferry to visit Greenport on the North Fork or the wonderful busier village of Sag Harbor just north of the Hamptons .
  • Submitted: Sep 7, 2012
  • Stayed: Aug 2012