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Name: Montauk Oceanside Suites
Price range: $142

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Cheap Shelter Island Hotels

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

$87

includes taxes & fees

$76 per night

Dec 8 - Dec 9

Free Cancellation

Reserve now, pay when you stay

17.34 mi from city center

A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex Library.

Pool

Breakfast included

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

$70

includes taxes & fees

$60 per night

Dec 12 - Dec 13

Free Cancellation

Reserve now, pay when you stay

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 Saybrook Country Barn.

Pet friendly

Parking included

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

$354

includes taxes & fees

$310 per night

Nov 25 - Nov 26

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

Saybrook Point Resort & Marina

2 Bridge St, Old Saybrook, CT

$329

includes taxes & fees

$289 per night

Dec 4 - Dec 5

Free Cancellation

Reserve now, pay when you stay

14.87 mi from city center

With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be a 4-minute walk from Connecticut River and within a 5-minute drive of General William Hart House.

Pool

Hot Tub

The Bentley Hotel Southampton

161 Hills Station Rd, Southampton, NY

$191

includes taxes & fees

$167 per night

Dec 1 - Dec 2

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

Water's Edge Resort & Spa

1525 Boston Post Road, Westbrook, CT

$210

includes taxes & fees

$182 per night

Nov 24 - Nov 25

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

Montauk Manor

236 Edgemere St., Montauk, NY

$187

includes taxes & fees

$163 per night

Nov 25 - Nov 26

20.31 mi from city center

With a stay at Montauk Manor in Montauk, you'll be near the beach, just a 3-minute walk from Shadmoor State Park and 14 minutes by foot from The Hamptons Beaches.

Pool

Kitchen

Budget Host East End Hotel in Riverhead

30 Lake Avenue, Riverhead, NY

$112

includes taxes & fees

$98 per night

Nov 22 - Nov 23

Free Cancellation

Reserve now, pay when you stay

19.98 mi from city center

A stay at Budget Host East End Hotel in Riverhead places you in the heart of Riverhead, within a 10-minute walk of All Star Bowling and Suffolk Theater.

Pool

Parking included

The Harbor Front Inn

209 Front St, Greenport, NY

$162

includes taxes & fees

$142 per night

Nov 25 - Nov 26

2.61 mi from city center

When you a 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

Sound View Greenport

58775 County Rd 48, Greenport, NY

$162

includes taxes & fees

$142 per night

Dec 8 - Dec 9

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

Montauk Yacht Club

32 Star Island Rd, Montauk, NY

21.1 mi from city center

Located in Montauk, Montauk Yacht Club is on the waterfront, within a 5-minute walk of Lake Montauk and The Hamptons Beaches.

On private beach

Pool

Montauk Oceanside Suites

115 South Emerson Avenue, Montauk, NY

$142

includes taxes & fees

$125 per night

Nov 26 - Nov 27

20.69 mi from city center

When you a stay at Montauk Oceanside Suites in Montauk, you'll be near the beach, just steps from South Edison Beach and The Hamptons Beaches.

Kitchen

Parking 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.

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Shelter Island hotels essential information

Accommodation	4,669 hotels
Lowest Price	$70
Highest Price	$354
Popular hotels	Quality Inn Old Saybrook - Westbrook, Pier Blue Inn Old Saybrook - Essex, Gurney's Montauk Resort & Seawater Spa, Saybrook Point Resort & Marina, The Bentley Hotel Southampton, Water's Edge Resort & Spa, Montauk Manor, Budget Host East End Hotel in Riverhead, The Harbor Front Inn, Sound View Greenport, Montauk Yacht Club, Montauk Oceanside Suites

Most Recent Shelter Island Hotel Reviews

Water's Edge Resort & Spa

5 out of 5

Posted 1 day ago

CheapTickets Verified Review

"While we were only. At the resort for one night, it was very relaxing, great service comfortable rooms. At this time of year, it was also very affordable. "

A verified traveler stayed at Water's Edge Resort & Spa