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Nov 12 - Nov 13

Tonight

Nov 13 - Nov 14

Tomorrow night

Featured Shelter Island 5 Stars Hotels

3.59 mi from city center

$242 nightly

$276 total

Nov 13 - Nov 14

Total with taxes and fees

Guests of Sound View Greenport enjoy features like a private beach, free WiFi in public areas, and conference space. Self parking is available for USD 29 per night. The front desk is staffed 24 hours a day to help with luggage storage and concierge services. Other amenities at this beach hotel include a seasonal outdoor pool, a terrace, and a banquet hall.

On private beach

Pool

13.36 mi from city center

$151 nightly

$172 total

Nov 13 - Nov 14

Total with taxes and fees

Guests staying at The Atlantic Hotel enjoy an outdoor pool, outdoor tennis courts, and free WiFi in public areas. There's free parking if you drive. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.

Pool

Pet friendly

Free Cancellation

Reserve now, pay when you stay

13.71 mi from city center

$118 nightly

$135 total

Dec 3 - Dec 4

Total with taxes and fees

Renovated in 2023, The Bentley Hotel Southampton offers a seasonal outdoor pool, coffee in a common area, and laundry facilities. You can put free parking to good use if you drive. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a picnic area and a garden.

Pool

Pet friendly

16.59 mi from city center

At Sea Crest Resort, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. You'll find limited parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach hotel include laundry facilities, a garden, and a vending machine.

Pool

Free WiFi

Free Cancellation

Reserve now, pay when you stay

14.87 mi from city center

$291 nightly

$334 total

Nov 30 - Dec 1

Total with taxes and fees

Saybrook Point Resort & Marina features a marina, a full-service spa, and 2 outdoor pools. There's free parking and a free train station shuttle. The front desk is staffed 24/7 to help with tours or tickets, access to locker space, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this spa hotel include an indoor pool, a gym, and a sauna.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

15.48 mi from city center

$71 nightly

$82 total

Nov 19 - Nov 20

Total with taxes and fees

Pier Blue Inn Old Saybrook - Essex features free WiFi in public areas and barbecue grills. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. This smoke-free hotel also has a picnic area.

Pet friendly

Parking included

18.43 mi from city center

$359 nightly

$410 total

Nov 25 - Nov 26

Total with taxes and fees

Guests of Gurney's Montauk Resort & Seawater Spa have access to a private beach, a full-service spa, and an indoor pool. The front desk is staffed 24/7 to help with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, meeting rooms, and a conference center.

On private beach

Pool

Free Cancellation

Reserve now, pay when you stay

17.34 mi from city center

$101 nightly

$116 total

Nov 23 - Nov 24

Total with taxes and fees

At Quality Inn Old Saybrook - Westbrook, guests enjoy an indoor pool, a gym, and free WiFi in public areas. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a microwave in a common area.

Pool

Breakfast included

20.67 mi from city center

At Montauk Blue Hotel, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. Self parking is offered for USD 35 per day. The front desk has multilingual staff that can help with luggage storage, and offer advice about sights and eateries nearby. Other amenities at this beach hotel include a terrace, a vending machine, and a picnic area.

Pool

Hot Tub

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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.

Best 5 star hotels in Shelter Island

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Shelter Island. After all, treating yourself to the finer things is what vacations are about.

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Shelter Island hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Shelter Island 5 star hotels and resorts typically offer luxury amenities such as:

Gourmet restaurant
Full-service fitness center with pool
Luxury spa
Welcome gifts upon arrival
Top-of-the-line beds and linens
Designer personal care products
Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Shelter Island with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place:

Search hotels by price, ranging from $82 to $410
Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
Choose from 4,697 5 star hotels in Shelter Island!

Shelter Island hotels essential information

Accommodation	4,697 hotels
Lowest Price	$82
Highest Price	$410
Popular hotels	Gurney's Montauk Resort & Seawater Spa, Pier Blue Inn Old Saybrook - Essex, Montauk Blue Hotel, Sound View Greenport, Quality Inn Old Saybrook - Westbrook, The Atlantic Hotel, Saybrook Point Resort & Marina, The Bentley Hotel Southampton, Sea Crest Resort