Photo by Brian V. Rowe

Find Historic Hotels in Shelter Island Heights, NY

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Our top choices for Shelter Island Heights historic hotels

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Hero Beach Club

Hero Beach Club

4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
$232 nightly
The price is $265
Dec 28 - Dec 29
Total with taxes and fees
Hero Beach Club
Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

4.0 star property
East Hampton
9.8 out of 10, Exceptional, (161)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
$279 nightly
The price is $363
Dec 14 - Dec 15
Total with taxes and fees
The 1770 House Restaurant & Inn
Garden
The Maidstone

The Maidstone

4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
$278 nightly
The price is $318
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Maidstone
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center
9.6 out of 10, Exceptional, (39)
"Great property, would stay here again."
United States
charles b.
$450 nightly
The price is $509
Dec 14 - Dec 15
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Property grounds
American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3

Greenport
$297 nightly
The price is $339
Jan 1 - Jan 2, 2026
Total with taxes and fees
American Beech in Greenport - King Suite 3
1 bedroom, iron/ironing board, internet
American Beech in Greenport NY - King Suite 1

American Beech in Greenport NY - King Suite 1

Greenport
10.0 out of 10, Exceptional, (5)
"Perfect Great place"
United States
Dean J.
$267 nightly
The price is $305
Dec 11 - Dec 12
Total with taxes and fees
American Beech in Greenport NY - King Suite 1
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$242 nightly
The price is $277
Dec 11 - Dec 12
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Outdoor dining
American Beech - Deluxe King Suite 14

American Beech - Deluxe King Suite 14

Greenport
10.0 out of 10, Exceptional, (2)
"Right in the heart of Greenport Villiage "
United States
Suzanne B.
$324 nightly
The price is $370
Dec 11 - Dec 12
Total with taxes and fees
American Beech - Deluxe King Suite 14
Property grounds
American Beech in Greenport - Deluxe King Suite 12

American Beech in Greenport - Deluxe King Suite 12

Greenport
$301 nightly
The price is $344
Dec 11 - Dec 12
Total with taxes and fees
American Beech in Greenport - Deluxe King Suite 12
Property grounds
American Beech in Greenport - Deluxe King Suite 11

American Beech in Greenport - Deluxe King Suite 11

Greenport
$301 nightly
The price is $344
Dec 11 - Dec 12
Total with taxes and fees
American Beech in Greenport - Deluxe King Suite 11
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 Heights Hotel Reviews

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

10/10 Excellent
"Very clean room Did not have the breakfast as we left prior to it starting. Would stay there again "
John 1-night trip
Posted 2 days ago
Sleep Inn & Suites Niantic North

Frequently asked questions

What should a history enthusiast expect from a trip to Shelter Island Heights?
The historical places in Shelter Island Heights are likely at the top of your sightseeing list. Why not appreciate the beaches during your visit?
How many historical hotels will I find in Shelter Island Heights?
Shelter Island Heights is home to 55 lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Shelter Island Heights?
Shelter Island Heights is notable for landmarks like Sylvester Manor. Natural beauty is on display at Sunset Beach, Crescent Beach, and Menhadden Lane Beach. Additionally, you might want to add Shelter Island Country Club to your agenda.
What is a historic hotel like in Shelter Island Heights?
When you book a historic hotel, you'll sleep someplace that has an official historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be considered a historic hotel as long as it has special significance. Traditional architecture and period features are typically found in the public spaces and guestrooms of these historic hotels in Shelter Island Heights, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of a historic hotel tends to be the most significant aspect. For a heritage hotel, it's often the cultural value as well as how it shaped the community.
Do historic hotels in Shelter Island Heights have modern facilities?
Hotels have the safety features and modern conveniences you've come to expect, but every effort is made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the popular amenities found at a contemporary hotel will also be available in a historic hotel. Rest assured that when you choose a historic hotel in Shelter Island Heights, you won't find a place that's uncomfortable or rundown.

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