Shelter Island Retreat

$ 1,735 per night

Shelter Island

Shelter Island,

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Entire home |

Entire home

Villa|

Villa

10 Guests

| 5 Bedrooms|

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Listing Description

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!

Room Description:
Bedroom 1: King Bed – Ensuite BA
Bedroom 2: King Bed – Ensuite BA
Bedroom 3: 2 Twin Beds – Ensuite BA
Bedroom 4: 2 Twin Bunk Beds – Ensuite BA
Bedroom 5: Queen Bed – Ensuite BA
Bedroom6 (bonus room): King Bed – Ensuite BA

8.625% tax included in rates.

Price Info

Price per night: $ 1,735

Price per weekend (Friday and Saturday) : $ 1,735

Cleaning Fee: $ 450 Single Fee

Minimum no of nights: 3

Security deposit: $ 2,500

Sleeping Situation

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single

Bedroom 4

2 Single

Bedroom 5

1 Queen Bed

Address

Address: Exact location information is provided after a booking is confirmed.

City: Shelter Island

County: United States

Zip: 11964

Country: United States

Details

Property ID: 29784

Property Size: 5,000 ft²

Rooms: 5

Bedrooms: 5

Bathrooms: 6.5

Check-in Hour: 3:00 PM

Check-Out Hour: 10:00AM

Features

Other Features

Air conditioning

Beach chairs

Beach front

Bed linen

Blender

Canoe kayak

Central heating

Cooking utensils

Dishwasher

Essentials

Iron and board

Kitchen stove

Near ocean

Ocean view

Oven

Parking

Pool table

Private heated outdoor swimming pool

Refrigerator

Smoking not allowed

Swimming pool

Toaster

Towel set

TV cable

TV satellite

Washbasin

Washing machine

Terms and Conditions

Smoking Allowed

Pets Allowed

Party Allowed

Children Allowed

Cancellation PolicyThis booking is eligible for a 100% refund 2 weeks prior booking at 3:00 PM.After that, this booking is eligible for an Evolve Future Travel Credit for 100% of what you’ve paid for if cancelled 2 days before booking, at 3:00 PM.After that, no refundable.

Availability

November 2025

M	T	W	T	F	S	S
	1 $ 1,735	2 $ 1,735
3 $ 1,735	4 $ 1,735	5 $ 1,735	6 $ 1,735	7 $ 1,735	8 $ 1,735	9 $ 1,735
10 $ 1,735	11 $ 1,735	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3
17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3
24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3

December 2025

M	T	W	T	F	S	S
1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3
8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3
15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3
22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3
29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

January 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3
5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3
12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3
19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3
26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

February 2026

M	T	W	T	F	S	S
	1 $ 1,735 3
2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3
9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3
16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3
23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3

March 2026

M	T	W	T	F	S	S
	1 $ 1,735 3
2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3
9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3
16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3
23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3
30 $ 1,735 3	31 $ 1,735 3

April 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3
6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3
13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3
20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3
27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3

May 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3
4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3
11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3
18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3
25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

June 2026

M	T	W	T	F	S	S
1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3
8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3
15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3
22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3
29 $ 1,735 3	30 $ 1,735 3

July 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3
6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3
13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3
20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3
27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

August 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3
3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3
10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3
17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3
24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3
31 $ 1,735 3

September 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3
7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3
14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3
21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3
28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3

October 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3
5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3
12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3
19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3
26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

November 2026

M	T	W	T	F	S	S
	1 $ 1,735 3
2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3
9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3
16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3
23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3
30 $ 1,735 3

December 2026

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3
7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3
14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3
21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3
28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

January 2027

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3
4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3
11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3
18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3
25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

February 2027

M	T	W	T	F	S	S
1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3
8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3
15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3
22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3

March 2027

M	T	W	T	F	S	S
1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3
8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3
15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3
22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3
29 $ 1,735 3	30 $ 1,735 3	31 $ 1,735 3

April 2027

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3
5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3
12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3
19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3
26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3

May 2027

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3
3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3	7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3
10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3	14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3
17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3	21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3
24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3	28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3
31 $ 1,735 3

June 2027

M	T	W	T	F	S	S
	1 $ 1,735 3	2 $ 1,735 3	3 $ 1,735 3	4 $ 1,735 3	5 $ 1,735 3	6 $ 1,735 3
7 $ 1,735 3	8 $ 1,735 3	9 $ 1,735 3	10 $ 1,735 3	11 $ 1,735 3	12 $ 1,735 3	13 $ 1,735 3
14 $ 1,735 3	15 $ 1,735 3	16 $ 1,735 3	17 $ 1,735 3	18 $ 1,735 3	19 $ 1,735 3	20 $ 1,735 3
21 $ 1,735 3	22 $ 1,735 3	23 $ 1,735 3	24 $ 1,735 3	25 $ 1,735 3	26 $ 1,735 3	27 $ 1,735 3
28 $ 1,735 3	29 $ 1,735 3	30 $ 1,735 3

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Adults

Ages 13 or above

Children

Ages 2 to 12

Infants

Under 2 years

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Shelter Island Retreat

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