Explore top 2026 4 Star Hotels in Shelter Island

Name: Topping Rose House
Price range: $1,133 total
Rating: 9

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Top Shelter Island 4 Star hotels

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,043 nightly

$1,192 total

Jul 15 - Jul 16

Total with taxes and fees

This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside ...

8.4/10 Very Good! (822 reviews)

"-"

Reviewed on Jul 10, 2026

Montauk Yacht Club

32 Star Island Rd Montauk NY

$766 nightly

$875 total

Jul 26 - Jul 27

Total with taxes and fees

This luxury hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi ...

8.6/10 Excellent! (1,006 reviews)

"Lackluster staff service while somehow still being pretentious. There are better places to visit and better places to stay."

Reviewed on Jul 13, 2026

Sound View Greenport

58775 County Rd 48 Greenport NY

$525 nightly

$600 total

Jul 22 - Jul 23

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with ...

8.4/10 Very Good! (665 reviews)

"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

Marram

21 Oceanview Terrace Montauk NY

$780 nightly

$891 total

Jul 16 - Jul 17

Total with taxes and fees

A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage ...

Offshore Montauk

71 S Emerson Ave Montauk NY

$629 nightly

$719 total

Jul 28 - Jul 29

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. Express check-out and luggage storage ...

9.4/10 Exceptional! (158 reviews)

"very clean and well maintained property. All newly renovated. Nice pool and beach access and amenities. only downside no elevator s to bring up luggage nor any dressers or closets in the room . only 3 hooks to hang clothes on."

Reviewed on Jul 13, 2026

The Pridwin Hotel

81 Shore Road Shelter Island Heights NY

$700 nightly

$800 total

Jul 19 - Jul 20

Total with taxes and fees

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. ...

9.6/10 Exceptional! (92 reviews)

"Stunning hotel! Will def stay again!"

Reviewed on Jul 13, 2026

The Maidstone

207 Main Street East Hampton NY

$637 nightly

$728 total

Aug 2 - Aug 3

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Free perks include continental breakfast, free self parking, and a beach shuttle. Free WiFi in public ...

Faraway Sag Harbor

31 West Water Street Sag Harbor NY

$1,271 nightly

$1,452 total

Jul 27 - Jul 28

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free valet parking and free WiFi. Free self parking, ...

Journey East Hampton

490 Pantigo Road East Hampton NY

$678 nightly

$775 total

Jul 20 - Jul 21

Total with taxes and fees

A seasonal outdoor pool, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and ...

9.2/10 Wonderful! (185 reviews)

"Very clean and great staff"

Reviewed on Jun 27, 2026

Topping Rose House

One Bridgehampton - Sag Harbor Turnpike Bridgehampton NY

$989 nightly

$1,133 total

Jul 19 - Jul 20

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public ...

9/10 Wonderful! (152 reviews)

"Amazing"

Reviewed on May 29, 2026

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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.

4 Star Hotels Shelter Island

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Shelter Island 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Shelter Island will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Shelter Island, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.