Hotels in Shelter Island

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Oct 16 - Oct 17
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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
Reserve now, pay when you stay
15.48 mi from city center
$89 nightly
The price is $102 total per night
$102 total
Oct 19 - Oct 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
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
$363 nightly
The price is $415 total per night
$415 total
Nov 13 - Nov 14
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 securing valuables, concierge services, 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
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
$94 nightly
The price is $108 total per night
$108 total
Nov 2 - Nov 3
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
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
20.67 mi from city center
$119 nightly
The price is $136 total per night
$136 total
Nov 9 - Nov 10
Total with taxes and fees
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
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
21.02 mi from city center
$280 nightly
The price is $320 total per night
$320 total
Oct 29 - Oct 30
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 banquet hall, a garden, and a gift shop.
Pool
Parking included
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
3.59 mi from city center
$266 nightly
The price is $304 total per night
$304 total
Oct 26 - Oct 27
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 concierge services and luggage storage. Other amenities at this beach hotel include a seasonal outdoor pool, a terrace, and a banquet hall.
On private beach
Pool
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 $334 total per night
$334 total
Nov 6 - Nov 7
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
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
13.36 mi from city center
$161 nightly
The price is $184 total per night
$184 total
Oct 19 - Oct 20
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
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
$150 nightly
The price is $171 total per night
$171 total
Nov 2 - Nov 3
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
$224 nightly
The price is $258 total per night
$258 total
Oct 19 - Oct 20
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, securing valuables, and luggage storage. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
On private beach
Pool
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave, Montauk, NY
20.51 mi from city center
$252 nightly
The price is $288 total per night
$288 total
Oct 30 - Oct 31
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 Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
2.61 mi from city center
$208 nightly
The price is $238 total per night
$238 total
Nov 2 - Nov 3
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 concierge services. Additional amenities include a terrace and a TV in a common area.
Pool
Breakfast included
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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
4,730 hotels
Lowest Price
$102
Highest Price
$415
Popular hotels
Pier Blue Inn Old Saybrook - Essex, Gurney's Montauk Resort & Seawater Spa, Quality Inn Old Saybrook - Westbrook, Montauk Blue Hotel, Marram, Sound View Greenport, Saybrook Point Resort & Marina, The Atlantic Hotel, The Bentley Hotel Southampton, Water's Edge Resort & Spa, Offshore Montauk, The Harbor Front Inn

Recent Reviews

Montauk Blue Hotel

Montauk Blue Hotel

5/5 Excellent
"Didn’t get to stay the night had a family emergency had to leave an hour after I checked in. Hope to get credited for another stay in the future. Staff was very nice. "
A verified traveler stayed at Montauk Blue Hotel
Posted 4 days ago
Montauk Blue Hotel

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