Shelter Island 4 Stars Hotels

  • 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 availability on Shelter Island 4 Star Hotels

Our top choices for Shelter Island 4-star hotels

Exterior

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (739 reviews)
"Room was spotless, staff were great and the resort is top notch!!"
United States
Carrie
The price is HK$2,517
HK$3,452 total
includes taxes & fees
23 Mar - 24 Mar
Gurney's Montauk Resort & Seawater Spa
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (621 reviews)
"The hotel was exceptional! We love staying at soundview during the winter months! "
United States
Christina
The price is HK$1,345
HK$1,761 total
includes taxes & fees
5 Apr - 6 Apr
Sound View Greenport
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (165 reviews)
"Amazing stay"
United States
Liana
The price is HK$1,446
HK$1,817 total
includes taxes & fees
26 Mar - 27 Mar
Journey East Hampton
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (348 reviews)
"Staff and hotel are lovely "
United States
Steven
The price is HK$1,767
HK$2,032 total
includes taxes & fees
31 Mar - 1 Apr
Madison Beach Hotel
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (152 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is HK$2,018
HK$2,305 total
includes taxes & fees
2 Apr - 3 Apr
The Maidstone
2 restaurants, breakfast served

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
"Wonderful hotel and location "
United States
FIONA
Montauk Yacht Club
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (148 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (143 reviews)
"Everything and everyone was just lovely! Comfortable Welcoming Great restaurant "
United States
Rachelle
The price is HK$3,987
HK$4,583 total
includes taxes & fees
26 Mar - 27 Mar
Topping Rose House
On the beach, sun-loungers, beach towels

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (203 reviews)
"Great weekend trip "
United States
Timothy
The price is HK$1,361
HK$2,352 total
includes taxes & fees
26 Mar - 27 Mar
Hero Beach Club
Courtyard view

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
"Beautiful resort in a great location "
United States
Nikki
The price is HK$1,481
HK$3,258 total
includes taxes & fees
15 Apr - 16 Apr
Marram
Beach nearby, white sand, sun-loungers, beach umbrellas

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (94 reviews)
"Thank you to the crew at The Roundtree for making our stay memorable! This is our second stay, so we couldn't turn down the evening smores by the fire and delivered warm cookies for a late night snack. The grounds and room were so beautiful. We will be back."
United States
Glenn
The price is HK$4,656
HK$5,585 total
includes taxes & fees
24 Mar - 25 Mar
The Roundtree, Amagansett
Exterior

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (509 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is HK$2,186
HK$2,513 total
includes taxes & fees
24 Mar - 25 Mar
Copper Beech Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel
Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is HK$2,366
HK$2,627 total
includes taxes & fees
1 Apr - 2 Apr
James Pharmacy Bed & Breakfast
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
Faraway Sag Harbor
Living area

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is HK$4,301
HK$5,808 total
includes taxes & fees
30 Mar - 31 Mar
Offshore Residences
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
Canoe Place Waterfront Residences
Exterior

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18 reviews)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Front of property

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (37 reviews)
"Great hosts"
United States
David
434 on Main
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island.
Mill House Inn

Mill House Inn

31 North Main Street East Hampton NY
The price is HK$1,958 per night from 22 Mar to 23 Mar
HK$1,958
HK$2,461 total
22 Mar - 23 Mar
includes taxes & fees
9/10 Wonderful! (81 reviews)
Still don't see what you're looking for?
See all properties in Shelter Island.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4/10 Poor
"My second stay but big disappointment the pool and hot tub wasn’t available for hotel guests this is the second time for me last year same thing happened they closed the spa area there was only pool opened, our room didn’t have any coffee cups no wine glass no any other glass wear, the bathroom need some attention leaking sink and we found many ants in the room "
petra 2-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are the best 4-star hotels in Shelter Island?
Make unforgettable memories in Shelter Island at Topping Rose House. A favourite with Expedia customers, this 4-star hotel offers loads of conveniences for a relaxing and comfortable stay.
How much does it cost to stay in a 4-star hotel in Shelter Island?
To lock in a 4-star hotel in Shelter Island that fits your budget, make use of Expedia's filters. Check out what's available during your preferred dates and use our pricing filter to set your maximum rate. You can also sort your results by the most economical option first.

  • Search for the lowest price from HK$2,461

What's the difference between 5-star and 4-star hotels in Shelter Island?
Treat yourself to luxury living during your Shelter Island getaway by choosing a 4-star hotel. As well as featuring upscale surroundings, these properties are typically packed with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go the extra mile to make your trip an even more lavish and memorable one. 24-hour concierge assistance, elegant décor and world-class dining are only the start of the exclusive conveniences and services you'll likely get access to.

Explore a world of travel with Expedia