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Name: The Harbor Front Inn
Price range: $188 total

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Cheap Shelter Island Hotels

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$459 nightly

$524 total

Mar 17 - Mar 18

Total with taxes and fees

18.43 mi from city center

Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State Park.

On private beach

Pool

Montauk Manor

236 Edgemere St. Montauk NY

$148 nightly

$169 total

Mar 5 - Mar 6

Total with taxes and fees

20.31 mi from city center

When you stay at Montauk Manor in Montauk, you'll be near the beach, within a 15-minute walk of The Hamptons Beaches and Shadmoor State Park.

Pool

Hot Tub

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$104 nightly

$120 total

Mar 5 - Mar 6

Total with taxes and fees

Free Cancellation

15.48 mi from city center

Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park.

Pet friendly

Parking included

Sound View Greenport

58775 County Rd 48 Greenport NY

$175 nightly

$200 total

Mar 5 - Mar 6

Total with taxes and fees

3.59 mi from city center

When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.

On private beach

Pool

Hyatt Place Long Island East End

451 East Main Street Riverhead NY

$118 nightly

$135 total

Mar 18 - Mar 19

Total with taxes and fees

19.5 mi from city center

With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All Star Bowling.

Pool

Pet friendly

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

20.67 mi from city center

With a stay at Montauk Blue Hotel in Montauk (Downtown Montauk), you'll be steps from The Hamptons Beaches and South Edison Beach.

Pool

Hot Tub

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$184 nightly

$212 total

Apr 1 - Apr 2

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

15.59 mi from city center

With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.

On private beach

Pool

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

$135 nightly

$154 total

Mar 10 - Mar 11

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

13.71 mi from city center

When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.

Pool

Pet friendly

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

$101 nightly

$116 total

Mar 10 - Mar 11

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

17.32 mi from city center

A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, within a 10-minute drive of Essex Steam Train and Essex Library.

Pool

Breakfast included

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

$311 nightly

$357 total

Mar 9 - Mar 10

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

14.89 mi from city center

With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be steps from Fort Saybrook Monument Park and a 2-minute drive from General William Hart House.

Pool

Hot Tub

Offshore Montauk

71 S Emerson Ave Montauk NY

$166 nightly

$190 total

Mar 8 - Mar 9

Total with taxes and fees

20.51 mi from city center

When you stay at Offshore Montauk in Montauk, you'll be near the beach, just steps from The Hamptons Beaches and Kirk Park Beach.

Pool

Pet friendly

The Harbor Front Inn

209 Front St Greenport NY

$165 nightly

$188 total

Mar 17 - Mar 18

Total with taxes and fees

2.61 mi from city center

When you stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.

Pool

Breakfast included

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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.

Shelter Island hotels essential information

Accommodation	4,708 hotels
Lowest Price	$116
Highest Price	$524
Popular hotels	Gurney's Montauk Resort & Seawater Spa, Montauk Manor, Pier Blue Inn Old Saybrook - Essex, Sound View Greenport, Hyatt Place Long Island East End, Montauk Blue Hotel, Water's Edge Resort & Spa, The Bentley Hotel Southampton, Quality Inn Old Saybrook - Westbrook, Saybrook Point Resort & Marina, Offshore Montauk, The Harbor Front Inn

Most Recent Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

4 out of 5

Posted 3 hours ago

CheapTickets Verified Review

"I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly disappointed to get a call on our check In day to tell us the indoor pool could not be used. That was literally what we wanted to do for the weekend was relax at the pool and eat and drink. I booked the trips weeks prior so to get a call the day of saying we can’t use to pool during our stay was truly disappointing. They waived the resort fee for the inconvenience, otherwise the weekend was great. "

A verified traveler stayed at Gurney's Montauk Resort & Seawater Spa