Hotels in Shelter Island

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Top Rated Shelter Island Hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$443 nightly
The price is $507 total per night
$507 total
Jan 22 - Jan 23, 2026
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, securing valuables, and luggage storage. 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
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
15.59 mi from city center
$223 nightly
The price is $256 total per night
$256 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of Water's Edge Resort & Spa have access to a private beach, a full-service spa, and an indoor pool. You can put free valet parking to good use if you drive. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
On private beach
Pool
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
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 picnic area, and a vending machine.
Pool
Hot Tub
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
15.48 mi from city center
$68 nightly
The price is $78 total per night
$78 total
Jan 5 - Jan 6, 2026
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
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
20.51 mi from city center
$166 nightly
The price is $190 total per night
$190 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
Guests staying at Offshore Montauk enjoy an outdoor pool, free WiFi in public areas, and a picnic area. You can put free parking to good use if you drive. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours.
Pool
Pet friendly
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
13.71 mi from city center
$126 nightly
The price is $144 total per night
$144 total
Jan 4 - Jan 5, 2026
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 garden and a picnic area.
Pool
Pet friendly
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
14.87 mi from city center
$291 nightly
The price is $335 total per night
$335 total
Jan 3 - Jan 4, 2026
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 luggage storage, securing valuables, and dry cleaning/laundry. 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
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
20.31 mi from city center
$156 nightly
The price is $178 total per night
$178 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Guests staying at Montauk Manor enjoy an indoor pool, a 24-hour gym, and a sauna. Transportation is made easy with an area shuttle. The 24-hour front desk has staff standing by to help with securing valuables, luggage storage, and concierge services. Additional amenities include outdoor tennis courts, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
2.61 mi from city center
$164 nightly
The price is $187 total per night
$187 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
At The Harbor Front Inn, guests have access to a 24-hour gym, free WiFi in public areas, and a seasonal outdoor pool. Self parking is offered for USD 29 per day. Front-desk staff can assist with luggage storage and tours/tickets. Additional amenities include a terrace and a TV in a common area.
Pool
Breakfast included
Bayview Resort

Bayview Resort

2.5 out of 5
53 West Tiana Road Hampton Bays NY
17.64 mi from city center
Guests of Bayview Resort have access to a private beach, a marina, and a gym. If you drive, take advantage of free parking. The front desk has multilingual staff that can help with luggage storage and concierge services. Other amenities at this beach motel include free WiFi in public areas, meeting rooms, and a 24-hour business center.
On private beach
Pool
Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy Amagansett NY
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 picnic area, and a vending machine.
Pool
Free WiFi
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
3.59 mi from city center
$183 nightly
The price is $209 total per night
$209 total
Dec 25 - Dec 26
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
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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.

Where should you stay in Shelter Island?

What are the best hotels for a stay with my pet in Shelter Island?

Sunset Beach Hotel is a pet-friendly hotel with free WiFi, free parking, and private decks.

What are the best hotels in central Shelter Island?

These are some of the most popular hotels in the center of Shelter Island:

Close to central Shelter Island, you'll find interesting places to visit like Sunset Beach.

What are the best hotels close to Sylvester Manor?

Learn about the local history at this landmark, which is 1.8 mi from central Shelter Island. There are 13 hotels within a mile of Sylvester Manor, giving you plenty to choose from, and here are some of the top ones:

  • American Beech Hotel: Located 2.2 mi away, this 3.5-star inn features a restaurant, a bar, and iPod docks.
  • Dering Harbor Inn: Located 0.7 mi away, this condo resort has an outdoor pool, free WiFi, and free parking.
  • House on Chase Creek: Located 0.8 mi away, this B&B has free breakfast, free WiFi, and free parking.

Shelter Island hotels essential information

Accommodation
4,678 hotels
Lowest Price
$78
Highest Price
$507
Popular hotels
Gurney's Montauk Resort & Seawater Spa, Water's Edge Resort & Spa, Montauk Blue Hotel, Pier Blue Inn Old Saybrook - Essex, Offshore Montauk, The Bentley Hotel Southampton, Saybrook Point Resort & Marina, Montauk Manor, The Harbor Front Inn, Bayview Resort, Sea Crest Resort, Sound View Greenport

Recent Reviews

Offshore Montauk

Offshore Montauk

5/5 Excellent
"Hotel was beautiful !!"
A verified traveler stayed at Offshore Montauk
Posted 2 days ago
Offshore Montauk

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