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Holiday Homes in Shelter Island

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Shelter Island holiday homes

Coffee/tea maker, fridge, microwave, oven

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (55 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,178
includes taxes & fees
21 July - 22 July
Work and Play Special! Extended Stay Discount
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$665
includes taxes & fees
21 July - 22 July
American Beech in Greenport - Petite King Room 7
Sun-loungers, beach towels

The SandPiper

The SandPiper
Pipes Cove
9.8 out of 10, Exceptional, (43 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is AU$719
includes taxes & fees
17 Aug - 18 Aug
The SandPiper
Sun-loungers, beach towels

Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (39 reviews)
"great anf friendly, clean"
United States
Sophia
The price is AU$719
includes taxes & fees
12 Aug - 13 Aug
Aqua Vista
Beach

Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (7 reviews)
"Everything was so nice and clean. Location was great, walking distance from everything. My children had an amazing time. I would book this again in the summer."
United States
Jessica0610@gmail.com A.
Beach Block Hideaway
Sun-loungers, beach towels

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$1,039
includes taxes & fees
23 July - 24 July
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AU$583
includes taxes & fees
21 July - 22 July
Adorable Cottage, 5 min walk to water & town
Interior

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is AU$10,090
includes taxes & fees
12 Aug - 13 Aug
Sag Harbor Water View w Dock 1.5ml from town
Property grounds

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is AU$775
includes taxes & fees
21 July - 22 July
American Beech in Greenport - Deluxe King 6
Beach nearby

The Bay Cottage ยท Rocky Neck Park, Beach & Niantic

The Bay Cottage ยท Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is AU$695
includes taxes & fees
21 July - 22 July
The Bay Cottage ยท Rocky Neck Park, Beach & Niantic
Interior

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is AU$5,991
includes taxes & fees
27 July - 28 July
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (6 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is AU$2,783
includes taxes & fees
26 July - 27 July
BlackBerry Private home with jacuzzi yearlong
Beach nearby, sun-loungers, beach towels

Central Private Pool Bridgehampton home

Central Private Pool Bridgehampton home
Sag Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house and property were so nice. We have a 10 and 11 year old. They played outside or were swimming in the pool the entire time. It's close to great shopping and beaches. It was a very relaxing and enjoyable long weekend. Everything was perfect!"
United States
Heather M.
The price is AU$3,876
includes taxes & fees
24 July - 25 July
Central Private Pool Bridgehampton home
Private kitchen

Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
The price is AU$1,965
includes taxes & fees
3 Aug - 4 Aug
Spacious house in East Hampton with heated pool + WFH
Outdoor dining

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (25 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AU$2,645
includes taxes & fees
21 July - 22 July
Villa Luz Family Home w/ heated pool & jacuzzi
Beach nearby

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is AU$1,187
includes taxes & fees
21 July - 22 July
adorable ranch in beach community
Interior

Chic Modern Retreat in the Heart of EH! Pool Open!

Chic Modern Retreat in the Heart of EH! Pool Open!
East Hampton
10.0 out of 10, Exceptional, (13 reviews)
"Great location and amenities. "
Canada
Bryan A.
The price is AU$5,177
includes taxes & fees
27 July - 28 July
Chic Modern Retreat in the Heart of EH! Pool Open!
Coffee/tea maker, fridge, microwave, oven

East Hampton Luxury: Heated Pool, Hot Tub and Expansive Yard with 6 Bedrooms

East Hampton Luxury: Heated Pool, Hot Tub and Expansive Yard with 6 Bedrooms
East Hampton North
9.8 out of 10, Exceptional, (43 reviews)
"Everything about the house, the hot tub, yard and rooms was perfect. Exactly as listed. Owner was extremely accommodating. "
United States
Dorie k.
The price is AU$5,609
includes taxes & fees
26 July - 27 July
East Hampton Luxury: Heated Pool, Hot Tub and Expansive Yard with 6 Bedrooms
Smart TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AU$849
includes taxes & fees
13 Aug - 14 Aug
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Beach nearby, sun-loungers, beach towels

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is AU$1,712
includes taxes & fees
26 July - 27 July
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Beautifully setting , wonderful hotel , good service and excellent restaurant"
Razvan 2-night trip
Posted 2 hours ago
Saybrook Point Resort & Marina

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
336
Accommodation
1342 Holiday Homes
Lowest Price
AU$583
Highest Price
AU$10,090