Find Romantic Hotels in Shelter Island, NY

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Check availability on Shelter Island Romantic Hotels

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Shelter Island romantic hotels

Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is NT$5,831
NT$6,662 total
includes taxes & fees
Jan 11 - 2026/1/12
The Shoals Suites and Slips
Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is NT$4,998
NT$5,748 total
includes taxes & fees
Dec 29 - Dec 30
Inn at Harbor Hill Marina
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1001)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is NT$9,713
NT$11,956 total
includes taxes & fees
Dec 29 - Dec 30
Saybrook Point Resort & Marina
Property grounds
The Hampton Maid

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The Hampton Maid
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (177)
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
The price is NT$7,118
NT$7,901 total
includes taxes & fees
Dec 29 - Dec 30
Westbrook Inn B&B
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is NT$7,921
NT$10,308 total
includes taxes & fees
Dec 28 - Dec 29
American Beech Hotel
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
Southampton
8.6 out of 10, Excellent, (551)
"Such a great location!"
United States
Elizabeth
The price is NT$6,287
NT$7,695 total
includes taxes & fees
Dec 29 - Dec 30
Southampton Inn
Exterior
Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (341)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is NT$8,656
NT$9,954 total
includes taxes & fees
Jan 1 - 2026/1/2
Madison Beach Hotel
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.
View all properties

Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The room was beautiful and staff was exceptional!"
Emily 1-night trip
Posted 5 days ago
Saybrook Point Resort & Marina

Frequently asked questions

Searching for romantic hotels in Shelter Island?
If you and your partner need some romantic time away, we've got just the ticket. If you want to explore the area, you might head to Sunset Beach, Shelter Island Historical Society, or Shelter Island Whale's Tail. If you're interested in staying near a certain attraction, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Shelter Island?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Shelter Island: The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.
What is there to do in Shelter Island?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Shelter Island has to offer. You might think about visiting Sunset Beach, Shelter Island Historical Society, or Shelter Island Whale's Tail.
What's the best way to get to Shelter Island and around town during my romantic getaway?
These transportation options in Shelter Island might help your romantic trip go off without a hitch: To get to Shelter Island, you can fly into East Hampton, NY (HTO), which is the closest major airport, located 8.8 mi (14.2 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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