Hotels in Shelter Island

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Nov 15 - Nov 16
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Nov 16 - Nov 17
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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
$351 nightly
The price is $401 total per night
$401 total
Nov 24 - Nov 25
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
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
$71 nightly
The price is $82 total per night
$82 total
Nov 16 - Nov 17
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
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 vending machine, and a picnic area.
Pool
Hot Tub
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
3.59 mi from city center
$237 nightly
The price is $271 total per night
$271 total
Dec 15 - Dec 16
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
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
17.34 mi from city center
$101 nightly
The price is $116 total per night
$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
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
13.36 mi from city center
$151 nightly
The price is $172 total per night
$172 total
Nov 16 - Nov 17
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
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
$264 nightly
The price is $303 total per night
$303 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
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
$116 nightly
The price is $133 total per night
$133 total
Nov 19 - Nov 20
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
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
$221 nightly
The price is $254 total per night
$254 total
Dec 4 - Dec 5
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
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 garden, and a vending machine.
Pool
Free WiFi
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway Montauk NY
19.93 mi from city center
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.
Pool
Free WiFi
The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy, Wainscott, NY
9.43 mi from city center
$183 nightly
The price is $210 total per night
$210 total
Nov 23 - Nov 24
Total with taxes and fees
Guests of The Sagaponack enjoy free WiFi in public areas, a seasonal outdoor pool, and a communal living room. If you drive, put free parking to good use. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include a porter/bellhop, a gift shop, and a water dispenser.
Pool
Pet friendly
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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 Gardiner's Bay Country Club 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
4,682 hotels
Lowest Price
$82
Highest Price
$401
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, Water's Edge Resort & Spa, Sea Crest Resort, Beachcomber Resort at Montauk, The Sagaponack

Recent Reviews

Sound View Greenport

Sound View Greenport

5/5 Excellent
"Beautiful and unique property. We really enjoyed our weekend getaway "
A verified traveler stayed at Sound View Greenport
Posted 3 days ago
Sound View Greenport

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