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Find Historic Hotels in Shelter Island Heights, NY

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Nov 30 - Dec 1
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Top 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, (201)
"Hero hotel was incredibly adorable and meticulously clean. The staff is very friendly and accommodating. I would highly recommend staying here! "
United States
Sarah
$238 nightly
The price is $272
Dec 4 - Dec 5
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, (160)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
$310 nightly
The price is $403
Dec 2 - Dec 3
Total with taxes and fees
The 1770 House Restaurant & Inn
Deluxe Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
The Reform Club

The Reform Club

2.0 star property
Amagansett North
10.0 out of 10, Exceptional, (2)
"Unique property; lots of attention from staff; close to town."
United States
Cathleen
The Reform Club
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, (38)
"Great property, would stay here again."
United States
charles b.
$453 nightly
The price is $512
Dec 2 - Dec 3
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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.
$268 nightly
The price is $306
Dec 7 - Dec 8
Total with taxes and fees
American Beech in Greenport NY - King Suite 1
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Saybrook Manor
9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
$455 nightly
The price is $515
Dec 22 - Dec 23
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Property grounds
American Beech - King Suite 2

American Beech - King Suite 2

Greenport
10.0 out of 10, Exceptional, (2)
"Excellent one night stay."
United Kingdom
Patrick M.
$268 nightly
The price is $306
Dec 9 - Dec 10
Total with taxes and fees
American Beech - King Suite 2
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)
"Great job "
United States
emilio
$243 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
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
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.
$325 nightly
The price is $371
Dec 2 - Dec 3
Total with taxes and fees
American Beech - Deluxe King Suite 14
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

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

10/10 Excellent
"Very clean property and room, good breakfast options and very friendly staff. Clearly a new property and working to keep it that way. Great stay!"
william 10-night trip
Posted 8 hours ago
Best Western Niantic - New London/Mystic Area

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 54 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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