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Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.

Best Resorts in Shelter Island

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Resorts in Shelter Island

Ocean View One Bedroom Suite | Premium bedding, in-room safe, iron/ironing board, free rollaway beds

Oceanfront One Bedroom Suite | Terrace/patio

Gurney's Montauk Resort & Seawater Spa

4.0 star property

Montauk

8.2 out of 10, Very Good, (668)

8.2/10

Very Good

(668)

"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "

$527 nightly

The price is $603

$603 total

Sep 29 - Sep 30

Total with taxes and fees

Gurney's Montauk Resort & Seawater Spa

3 restaurants, breakfast, lunch, dinner served; Italian cuisine

Couples treatment rooms, sauna, hot tub, steam room, body treatments

Water's Edge Resort & Spa

3.5 star property

Westbrook Center

8.8 out of 10, Excellent, (1018)

8.8/10

Excellent

(1018)

"clean and quiet property, great views, amazing staff"

$219 nightly

The price is $252

$252 total

Oct 26 - Oct 27

Total with taxes and fees

Water's Edge Resort & Spa

Luxury Cottage, Bay View | 1 bedroom, Frette Italian sheets, premium bedding, down comforters

Luxury Cottage, Bay View | Private spa tub

Duryea's Sunset Cottages

2.5 star property

Montauk

10.0 out of 10, Exceptional, (3)

10/10

Exceptional

(3)

"Absolutely beautiful property. Everything was perfect. The staff are amazing. This an incredible place."

$1,570 nightly

The price is $1,794

$1,794 total

Oct 6 - Oct 7

Total with taxes and fees

Duryea's Sunset Cottages

2 bedrooms, desk, iron/ironing board, WiFi

Brand New Waterfront - Chic & Sophisticated Unit # 702

Culloden Shores

Brand New Waterfront - Chic & Sophisticated Unit # 702

2 bedrooms, iron/ironing board, WiFi, bed sheets

Brand New Waterfront - Chic & Sophisticated

Culloden Shores

7.0 out of 10, Good, (2)

7.0/10

Good

(2)

"The Host, Steve was very responsive and helpful. Accommodations are great for a couple, a young family, a small family, or even just some friends! Very spacious and we loved the en-suite bathrooms in the bedrooms. Kitchen was fully equipped with lots of tools. Ample pantry space to store your own goods! Laundry machines were great. Very spacious and great for our family getaway!"

Brand New Waterfront - Chic & Sophisticated

Brand New Waterfront - Chic & Sophisticated Unit # 703

Culloden Shores

10.0 out of 10, Exceptional, (6)

10/10

Exceptional

(6)

"Very comfortable space, great location, close to many restaurants and beaches"

Brand New Waterfront - Chic & Sophisticated Unit # 703

Brand New Waterfront - Chic & Sophisticated Unit # 704

Culloden Shores

Brand New Waterfront - Chic & Sophisticated Unit # 704

Fridge, microwave, stovetop, coffee/tea maker

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Westbrook Center

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook Center

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook Center

8.0 out of 10, Very Good, (1)

8.0/10

Very Good

(1)

"Comfortable space for a small family. We liked the flexibility of having a small beach on property and our own kitchen. The owner was easy to contact too."

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Cozy Pad 2BR Beachside Home | TennisPoolFreePKG Unit 721 | Terrace/patio

1 bedroom, desk, laptop workspace, bed sheets

Ocean Colony Beach and Tennis Club

2.0 star property

Amagansett

Ocean Colony Beach and Tennis Club

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Westbrook Center

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook Center

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

"Had a great stay for a long weekend getaway! The unit was in great shape, and we really enjoyed ourselves!"

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook Center

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

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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Top Shelter Island Hotel Reviews

Ocean Surf Resort

10/10 Excellent

"The view from our balcony was beautiful! We watched whales and dolphins swim by. Hotel is close to restaurants and town and very walkable. Would definitely stay again "

michelle 1-night trip

Posted 1 day ago

Ocean Surf Resort

The Bentley Hotel Southampton

10/10 Excellent

"Huge second floor suite. Full size fridge freezer and microwave. Excellent shower. Super comfortable beds. All spotlessly clean. Added bonus of an outdoor pool. Would not hesitate to stay in this hotel again. "

James 2-night trip

Posted 1 day ago

The Bentley Hotel Southampton

The Montauk Soundview

10/10 Excellent

"Great room! Loved being so close to the beach and boats!"

Giovanna 2-night trip

Posted 2 days ago

The Montauk Soundview

Saybrook Point Resort & Marina

10/10 Excellent

"Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful. "

Patricia 1-night trip

Posted 2 days ago

Saybrook Point Resort & Marina

Offshore Montauk

10/10 Excellent

"The accommodations were beautifully modern & clean. The staff was very friendly & hospitable. We loved it! It was perfect for our getaway!"

Arlette 3-night trip

Posted 2 days ago

Offshore Montauk

Montauk Blue Hotel

10/10 Excellent

"Great hotel, nice staff, clean and i loved the beach access. Only downfall was the 1 bathroom when not checked intoba room. Long line and humid"

Grazyna 1-night trip

Posted 2 days ago

Montauk Blue Hotel

Beachcomber Resort at Montauk

10/10 Excellent

"Perfect location fir a weekend getaway. The beach access was right across the road. You coul walk into town easily or if you wanted to d6ive everything was a close location to here."

Kaitlyn 2-night trip

Posted 3 days ago

Beachcomber Resort at Montauk

Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"Clean, quiet, friendly staff."

sharon 1-night trip

Posted 3 days ago

Quality Inn Old Saybrook - Westbrook

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Highly recommend!"

Christina 1-night trip

Posted 4 days ago

Pier Blue Inn Old Saybrook - Essex

Find out more about Shelter Island

Shelter Island Resorts information

Number of reviews	1,693
Accommodation	14 Resorts
Lowest Price	$252
Highest Price	$1,794

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Hotels near Shelter Island Historical Society
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Flights to Shelter Island Heights
Flights from Shelter Island Heights
Flights to Greenport

Shelter Island Historical Society
Havens House
Sylvester Manor
Wades Beach
Mashomack Preserve
Visit Shelter Island Heights
Sunset Beach
Shell Beach
Crescent Beach
Gardiner's Bay Country Club
Railroad Museum of Long Island
Camera Obscura
Visit Greenport

Car rentals near Shelter Island Heights
Car rentals near Dering Harbor
Car rentals near Greenport

Shelter Island Heights Vacation Rentals
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Things to do in Greenport

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Best Resorts in Shelter Island

Check prices for these dates

Resorts in Shelter Island

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

Water's Edge Resort & Spa

Water's Edge Resort & Spa

Duryea's Sunset Cottages

Duryea's Sunset Cottages

Brand New Waterfront - Chic & Sophisticated Unit # 702

Brand New Waterfront - Chic & Sophisticated Unit # 702

Brand New Waterfront - Chic & Sophisticated

Brand New Waterfront - Chic & Sophisticated

Brand New Waterfront - Chic & Sophisticated Unit # 703

Brand New Waterfront - Chic & Sophisticated Unit # 703

Brand New Waterfront - Chic & Sophisticated Unit # 704

Brand New Waterfront - Chic & Sophisticated Unit # 704

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Water's Edge Resort & Spa May 23, 2025 - May 30, 2025

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Ocean Colony Beach and Tennis Club

Ocean Colony Beach and Tennis Club

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Top Shelter Island Hotel Reviews

Ocean Surf Resort

Find out more about Shelter Island

Find out more about Shelter Island

Shelter Island Resorts information

Explore a world of travel with Expedia

Explore a world of travel with Expedia