Holiday Homes in Shelter Island

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 June - 14 June
In three months
10 July - 12 July
In four months
7 Aug - 9 Aug

Our top choices for Shelter Island holiday homes

Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is AU$1,808
includes taxes & fees
21 Apr - 22 Apr
Work and Play Special! Extended Stay Discount
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, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is AU$380
includes taxes & fees
26 Apr - 27 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is AU$707
includes taxes & fees
11 May - 12 May
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 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$622
includes taxes & fees
5 May - 6 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor dining

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (127 reviews)
"Great property!"
United States
Matthew B.
The price is AU$850
includes taxes & fees
24 Apr - 25 Apr
Coastal New England Waterfront Home, Harkness Park, Casinos
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$370
includes taxes & fees
20 Apr - 21 Apr
American Beech in Greenport - Petite King Room 7
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AU$843
includes taxes & fees
21 Apr - 22 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is AU$373
includes taxes & fees
26 Apr - 27 Apr
Stylish Modern Stay Steps from the Ocean
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "
United States
Karen B.
The price is AU$867
includes taxes & fees
22 Apr - 23 Apr
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is AU$806
includes taxes & fees
20 Apr - 21 Apr
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is AU$894
includes taxes & fees
20 Apr - 21 Apr
Renovated Townhouse walk to all
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is AU$1,911
includes taxes & fees
22 Apr - 23 Apr
Minutes from the beach, brand new 4 bedroom
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is AU$1,351
includes taxes & fees
20 Apr - 21 Apr
Beachfront Greenport Villa
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
Cozy 5 Bedroom With Wi-fi And Air Condition
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$3,898
includes taxes & fees
21 Apr - 22 Apr
Sag Harbor Water View w Dock 1.5ml from town
Property grounds

Waterfront tranquility near Sag Harbor Village

Waterfront tranquility near Sag Harbor Village
Bay Point
The price is AU$1,710
includes taxes & fees
20 Apr - 21 Apr
Waterfront tranquility near Sag Harbor Village
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is AU$1,246
includes taxes & fees
20 Apr - 21 Apr
Cozy Hamptons Escape 3BR Minutes From Beach!
Smart TV, fireplace

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is AU$8,737
includes taxes & fees
26 Apr - 27 Apr
Spacious 5-bedroom house with water views and 2 houses from the bay.
Property grounds

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is AU$2,380
includes taxes & fees
20 Apr - 21 Apr
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Was clean unique didnt expect to see the rooms so nice for the price and the rooms are unique in its own way"
Adela 1-night trip
Posted 1 hour ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Shelter Island

Shelter Island Holiday Homes information

Number of reviews
443
Accommodation
1611 Holiday Homes
Lowest Price
AU$370
Highest Price
AU$8,737