Hotels in Shelter Island

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May 30 - May 31
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May 31 - Jun 1
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Top Rated Shelter Island Hotels

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
15.48 mi from city center
$98 nightly
The price is $112 total per night
$112 total
Jun 7 - Jun 8
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.
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
$683 nightly
The price is $780 total per night
$780 total
Jun 1 - Jun 2
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.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
20.31 mi from city center
$286 nightly
The price is $327 total per night
$327 total
May 31 - Jun 1
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 luggage storage, securing valuables, and concierge services. Additional amenities include outdoor tennis courts, free WiFi in public areas, and a hot tub.
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
13.34 mi from city center
$191 nightly
The price is $218 total per night
$218 total
May 31 - Jun 1
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 free newspapers.
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
21.1 mi from city center
$409 nightly
The price is $467 total per night
$467 total
May 31 - Jun 1
Total with taxes and fees
Montauk Yacht Club features a private beach, a marina, and 2 outdoor pools. There's free parking and limo/town car service. The front desk has multilingual staff on hand 24/7 to help with luggage storage, concierge services, 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 hotel include an indoor pool, a children's pool, and a gym.
Marram

Marram

4 out of 5
21 Oceanview Terrace Montauk NY
21.02 mi from city center
$405 nightly
The price is $462 total per night
$462 total
May 31 - Jun 1
Total with taxes and fees
Guests of Marram enjoy free WiFi in public areas, a seasonal outdoor pool, and a terrace. There's free parking if you drive. 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 gift shop, a banquet hall, and a garden.
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
$264 nightly
The price is $304 total per night
$304 total
May 31 - Jun 1
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 tours or tickets, luggage storage, and securing valuables. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
20.51 mi from city center
$292 nightly
The price is $334 total per night
$334 total
Jun 2 - Jun 3
Total with taxes and fees
Guests of Offshore Montauk have access to an outdoor pool, a gym, and a sauna. You can put free parking to good use if you drive. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. Additional amenities include free WiFi in public areas, coffee/tea in a common area, and free use of bicycles.
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
13.71 mi from city center
$166 nightly
The price is $190 total per night
$190 total
Jun 7 - Jun 8
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.
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway Montauk NY
19.93 mi from city center
$294 nightly
The price is $332 total per night
$332 total
Jun 1 - Jun 2
Total with taxes and fees
At Beachcomber Resort at Montauk, guests have access to a gym, a sauna, and free WiFi in public areas. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include an outdoor tennis court, a seasonal outdoor pool, and a vending machine.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
3.59 mi from city center
$419 nightly
The price is $479 total per night
$479 total
May 31 - Jun 1
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.
Ocean Resort Inn

Ocean Resort Inn

2 out of 5
95 S Emerson Ave Montauk NY
20.61 mi from city center
$125 nightly
The price is $143 total per night
$143 total
Jun 3 - Jun 4
Total with taxes and fees
Guests of Ocean Resort Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. You can take advantage of free parking if you drive. Front-desk staff can help with concierge services, and provide local restaurant recommendations. This beach motel also has a garden.
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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:

Sunset Beach and Crescent Beach are a couple of sights to visit in the heart of Shelter Island.

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
4,812 hotels
Lowest Price
$112
Highest Price
$780
Popular hotels
Pier Blue Inn Old Saybrook - Essex, Gurney's Montauk Resort & Seawater Spa, Montauk Manor, The Atlantic Hotel, Montauk Yacht Club, Marram, Water's Edge Resort & Spa, Offshore Montauk, The Bentley Hotel Southampton, Beachcomber Resort at Montauk, Sound View Greenport, Ocean Resort Inn

Recent Reviews

Montauk Yacht Club

Montauk Yacht Club

5/5 Excellent
"Nice stay."
A verified traveler stayed at Montauk Yacht Club
Posted 3 hours ago
Montauk Yacht Club

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