Search Shelter Island Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

Aerial view

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,292 reviews)
"Nice pool, great restaurant "
United States
April
The price is AU$253
includes taxes & fees
5 Feb - 6 Feb
Montauk Manor
BBQ/picnic Area

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is AU$182
includes taxes & fees
9 Feb - 10 Feb
Hyatt Place Long Island East End
Restaurant

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (238 reviews)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is AU$253
includes taxes & fees
9 Feb - 10 Feb
The Shoals Suites and Slips
One Bedroom Harbor View Terrace Suite | View from room

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (564 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is AU$268
includes taxes & fees
17 Feb - 18 Feb
The Harbor Front Inn
View from property

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195 reviews)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is AU$234
includes taxes & fees
8 Feb - 9 Feb
American Beech Hotel
Lunch, dinner, brunch served; American cuisine, beach views

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (609 reviews)
"Nice place"
United States
Mateusz
The price is AU$290
includes taxes & fees
17 Feb - 18 Feb
Sound View Greenport

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (80 reviews)
"Great stay. The host is amzing and very helpful. The house is peaceful and safe!"
United States
Marshella
The price is AU$169
includes taxes & fees
10 Feb - 11 Feb
House on Chase Creek
Exterior

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (885 reviews)
"Big room Clean Needs bathroom update In general, we had a good day"
United States
Raz
Kenny's Tipperary Inn
Ocean View 2 Queens

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (100 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is AU$270
includes taxes & fees
17 Feb - 18 Feb
Offshore Montauk
Terrace/patio

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (433 reviews)
"Adorable room"
United States
Martin
The price is AU$207
includes taxes & fees
15 Feb - 16 Feb
The Bentley Hotel Southampton
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (150 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is AU$275
includes taxes & fees
15 Feb - 16 Feb
The Maidstone
Oceanfront 2BD Queen and 2 Twins | Terrace/patio

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is AU$245
includes taxes & fees
5 Feb - 6 Feb
Windward Shores Ocean Resort
Property grounds

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,004 reviews)
"Everything was perfect, from the room to the staff. "
United States
Kathleen
The price is AU$277
includes taxes & fees
5 Feb - 6 Feb
Inn at Harbor Hill Marina
Front of property

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (380 reviews)
"Very comfortable, clean, well-appointed room with a modern yet cozy feel. We stayed one night for a wedding. Would highly recommend!"
United States
Marcia
The price is AU$244
includes taxes & fees
9 Feb - 10 Feb
The Preston House & Hotel
Terrace/patio

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,002 reviews)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is AU$490
includes taxes & fees
8 Feb - 9 Feb
Saybrook Point Resort & Marina
Golf

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is AU$159
includes taxes & fees
5 Feb - 6 Feb
Hamlet Inn
Exterior detail

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is AU$178
includes taxes & fees
5 Feb - 6 Feb
Southampton Long Island Hotel
Outdoor pool, pool loungers

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (300 reviews)
"Clean room, courteous staff and great location "
United States
James
Daunt's Albatross Motel
Exterior

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,003 reviews)
"Room was clean and warm and the staff was very friendly "
United States
Pattie
Pier Blue Inn Old Saybrook - Essex
BBQ/picnic Area

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (981 reviews)
"Clean hotel and conveniently located! "
United States
Maria
The Atlantic Hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Very comfortable and enjoyable place to stay."
Stephen 1-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

Find out more about Shelter Island

Shelter Island Cottages information

Number of reviews
10,627
Accommodation
204 Cottages
Lowest Price
AU$159
Highest Price
AU$490