Compare Cheap Hotels in Shelter Island

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Cheap Shelter Island Hotels

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

$101

includes taxes & fees

$88 per night

Nov 12 - Nov 13

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

Sound View Greenport

58775 County Rd 48, Greenport, NY

$233

includes taxes & fees

$205 per night

Nov 14 - Nov 15

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

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

$512

includes taxes & fees

$449 per night

Nov 3 - Nov 4

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

$82

includes taxes & fees

$71 per night

Nov 4 - Nov 5

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 Crystal Lake Town Park.

Pet friendly

Parking included

Montauk Yacht Club

32 Star Island Rd, Montauk, NY

$284

includes taxes & fees

$249 per night

Oct 31 - Nov 1

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

Saybrook Point Resort & Marina

2 Bridge St, Old Saybrook, CT

$316

includes taxes & fees

$277 per night

Nov 3 - Nov 4

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

$188

includes taxes & fees

$168 per night

Nov 10 - Nov 11

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

Budget Host East End Hotel in Riverhead

30 Lake Avenue, Riverhead, NY

$112

includes taxes & fees

$98 per night

Nov 1 - Nov 2

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.

Baron's Cove

31 West Water Street, Sag Harbor, NY

$281

includes taxes & fees

$247 per night

Nov 4 - Nov 5

5.06 mi from city center

With a stay at Baron's Cove in Sag Harbor, you'll be near the beach, just a 2-minute walk from The Hamptons Beaches and 7 minutes by foot from Bay Street Theatre.

Beachcomber Resort at Montauk

727 Old Montauk Highway, Montauk, NY

19.93 mi from city center

With a stay at Beachcomber Resort at Montauk in Montauk, you'll be a 1-minute walk from The Hamptons Beaches and 8 minutes by foot from Second House Museum.

Pool

Free WiFi

Water's Edge Resort & Spa

1525 Boston Post Road, Westbrook, CT

$229

includes taxes & fees

$199 per night

Nov 4 - Nov 5

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 Sagaponack

3720 Montauk Hwy, Wainscott, NY

$239

includes taxes & fees

$214 per night

Nov 3 - Nov 4

9.43 mi from city center

With a stay at The Sagaponack in Wainscott, you'll be within a 5-minute drive of Wolffer Estates Vineyard and The Hamptons Beaches.

Pool

Pet friendly

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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	4,685 hotels
Lowest Price	$82
Highest Price	$512
Popular hotels	Quality Inn Old Saybrook - Westbrook, Sound View Greenport, Gurney's Montauk Resort & Seawater Spa, Pier Blue Inn Old Saybrook - Essex, Montauk Yacht Club, Saybrook Point Resort & Marina, The Bentley Hotel Southampton, Budget Host East End Hotel in Riverhead, Baron's Cove, Beachcomber Resort at Montauk, Water's Edge Resort & Spa, The Sagaponack