Hotels in Shelter Island

Name: The Harbor Front Inn
Price range: $334 total

Search over 4,787 hotels from $104

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

May 12 - May 13

Tonight

May 13 - May 14

Tomorrow night

Top Rated Shelter Island Hotels

18.43 mi from city center

$677 total

per night

May 17 - May 18

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

20.31 mi from city center

$192 total

per night

May 26 - May 27

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.

Pool

Hot Tub

21.1 mi from city center

$341 total

per night

May 13 - May 14

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.

On private beach

Pool

Free Cancellation

Reserve now, pay when you stay

13.71 mi from city center

$168 total

per night

May 21 - May 22

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

Free Cancellation

15.48 mi from city center

$104 total

per night

May 18 - May 19

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

3.59 mi from city center

$401 total

per night

May 27 - May 28

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.

20.67 mi from city center

$263 total

per night

May 13 - May 14

Guests of Montauk Blue Hotel enjoy features like an indoor pool, a hot tub, and a terrace. You'll find limited parking. 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 vending machine and a picnic area.

Pool

Hot Tub

5.05 mi from city center

$360 total

per night

May 25 - May 26

Sag Harbor Inn offers an outdoor pool, a seasonal outdoor pool, and coffee in a common area. Free parking is available if you drive. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations. Additional amenities include a meeting room, a vending machine, and a fireplace in the lobby.

15.59 mi from city center

$304 total

per night

May 20 - May 21

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.

On private beach

Pool

21.02 mi from city center

$394 total

per night

May 14 - May 15

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.

Pool

Parking included

2.61 mi from city center

$334 total

per night

May 19 - May 20

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.

20.59 mi from city center

$146 total

per night

May 13 - May 14

At Ocean Surf Resort, guests have access to free WiFi in public areas, a seasonal outdoor pool, and a terrace. Self parking is offered for USD 35 per day. Front-desk staff can assist with luggage storage, concierge services, and securing valuables. Other amenities at this beach motel include a picnic area, barbecue grills, and a reception hall.

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

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.

How much is a Shelter Island hotel?

Check Shelter Island hotel room prices by star rating

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:

Sound View Greenport is hotel has a private beach, 2 bars, and free breakfast.
The Harbor Front Inn is hotel has free breakfast, free WiFi, and a 24-hour fitness center.
The Shoals Suites and Slips is hotel has free WiFi, private balconies, and a business center.

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	4,787 hotels
Lowest Price	$104
Highest Price	$677
Popular hotels	Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Montauk Yacht Club, The Bentley Hotel Southampton, Pier Blue Inn Old Saybrook - Essex, Sound View Greenport, Montauk Blue Hotel, Sag Harbor Inn, Water's Edge Resort & Spa, Marram, The Harbor Front Inn, Ocean Surf Resort