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Independent in Shelter Island

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$466 nightly

$532 total

Dec 15 - Dec 16

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$79 nightly

$91 total

Dec 21 - Dec 22

Total with taxes and fees

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

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$244 nightly

$281 total

Dec 14 - Dec 15

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

Sound View Greenport

58775 County Rd 48 Greenport NY

$212 nightly

$242 total

Jan 12 - Jan 13, 2026

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.

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

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

$331 nightly

$380 total

Dec 14 - Dec 15

Total with taxes and fees

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 steps from Fort Saybrook Monument Park and 4 minutes by foot from Connecticut River.

Pool

Hot Tub

Offshore Montauk

71 S Emerson Ave Montauk NY

$166 nightly

$190 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

20.51 mi from city center

When you a 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 Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

$118 nightly

$135 total

Dec 22 - Dec 23

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

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 near the beach, just a 1-minute walk from The Hamptons Beaches and 8 minutes by foot from Second House Museum.

Pool

Free WiFi

Montauk Manor

236 Edgemere St. Montauk NY

$156 nightly

$178 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

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

Hot Tub

The Atlantic Hotel

1655 County Road 39 Southampton NY

$151 nightly

$172 total

Dec 14 - Dec 15

Total with taxes and fees

13.36 mi from city center

Located in Southampton, The Atlantic Hotel is by the ocean, within a 5-minute drive of Shinnecock Hills Golf Course and The Hamptons Beaches.

Pool

Pet friendly

Sea Crest Resort

2166 Montauk Hwy Amagansett NY

16.59 mi from city center

Located in Amagansett, Sea Crest Resort is on the beach, within a 5-minute walk of The Hamptons Beaches and Hither Hills State Park.

Pool

Free WiFi

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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	4,687 hotels
Lowest Price	$91
Highest Price	$532
Popular hotels	Gurney's Montauk Resort & Seawater Spa, Pier Blue Inn Old Saybrook - Essex, Water's Edge Resort & Spa, Sound View Greenport, Montauk Blue Hotel, Saybrook Point Resort & Marina, Offshore Montauk, The Bentley Hotel Southampton, Beachcomber Resort at Montauk, Montauk Manor, The Atlantic Hotel, Sea Crest Resort

Most Recent Shelter Island Hotel Reviews

Water's Edge Resort & Spa

5 out of 5

Posted 2 days ago

CheapTickets Verified Review

"The staff were all pleasant and helpful. View from the room was amazing. Place was decorated beautifully for Christmas. Beautiful wood burning fireplaces to sit by and relax. The perfect cold weather getaway"

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