Search Cottages in Shelter Island

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

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

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is ₩701,040
₩968,148 total
includes taxes & fees
Feb 10 - Feb 11
Offshore Residences

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (101 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is ₩169,918
₩277,737 total
includes taxes & fees
Feb 22 - Feb 23
Offshore Montauk

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

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 ₩202,848
₩260,394 total
includes taxes & fees
Feb 12 - Feb 13
Montauk Manor

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very Good, (723 reviews)
"Room was spotless, staff were great and the resort is top notch!!"
United States
Carrie
The price is ₩475,654
₩652,118 total
includes taxes & fees
Feb 22 - Feb 23
Gurney's Montauk Resort & Seawater Spa

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 ₩192,837
₩252,155 total
includes taxes & fees
Feb 11 - Feb 12
Windward Shores Ocean Resort

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (93 reviews)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is ₩869,898
₩1,043,546 total
includes taxes & fees
Feb 10 - Feb 11
The Roundtree, Amagansett

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (163 reviews)
"Amazing stay"
United States
Liana
Journey East Hampton

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (78 reviews)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is ₩365,888
₩459,833 total
includes taxes & fees
Feb 12 - Feb 13
Mill House Inn

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is ₩524,039
₩613,345 total
includes taxes & fees
Feb 23 - Feb 24
The Huntting Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162 reviews)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is ₩390,036
₩533,215 total
includes taxes & fees
Feb 10 - Feb 11
The 1770 House Restaurant & Inn

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 ₩260,000
₩297,048 total
includes taxes & fees
Feb 17 - Feb 18
The Maidstone

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
Wainscott
7.0 out of 10, Good, (9 reviews)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is ₩417,770
₩477,303 total
includes taxes & fees
Feb 10 - Feb 11
Wainscott Woods Retreat

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (223 reviews)
"The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!"
United States
Daren
The price is ₩222,606
₩312,851 total
includes taxes & fees
Mar 10 - Mar 11
The Sagaponack

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,005 reviews)
"Everything was perfect, from the room to the staff. "
United States
Kathleen
The price is ₩247,340
₩284,441 total
includes taxes & fees
Feb 10 - Feb 11
Inn at Harbor Hill Marina

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (141 reviews)
"Our second home :)"
United States
olivia
The price is ₩783,731
₩900,534 total
includes taxes & fees
Feb 16 - Feb 17
Topping Rose House

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (137 reviews)
"Quiet and warm and clean. Nice touch from Housekeeping too! "
United States
Jessica
The price is ₩168,601
₩193,891 total
includes taxes & fees
Feb 16 - Feb 17
The Niantic Inn

Bridgehampton Inn

Bridgehampton Inn
3.5 star property
Bridgehampton
9.4 out of 10, Exceptional, (221 reviews)
"Everything was excellent. Rooms were upgraded and were lovely, everything sparkling clean, staff most helpful. The breakfast was great. Would recommend and would stay again. "
United States
Patricia
The price is ₩393,841
₩449,954 total
includes taxes & fees
Feb 10 - Feb 11
Bridgehampton Inn

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (582 reviews)
"Lovely hotel, very clean and friendly! Definitely going back!"
United States
Hollie
The price is ₩300,028
₩342,782 total
includes taxes & fees
Feb 15 - Feb 16
Sag Harbor Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Shelter Island Cottages information

Number of reviews
6,136
Accommodation
61 Cottages
Lowest Price
₩193,891
Highest Price
₩1,043,546

Frequently asked questions

Why book your cottage in Shelter Island with Expedia?
We think a getaway should be easy, so if you're seeking cottages in Shelter Island at an affordable rate, Expedia has your back. Keep the budget under control and pick a thrifty option far from the hustle and bustle, or book a 5-star cottage to pamper your favorite people.
How can I find cheap cottages in Shelter Island?
With Expedia's handy filter tool, locating cheap cottages in Shelter Island is easy. To discover properties that'll make your hip pocket happy, narrow your search by amenities, star rating and budget.