Photo by Brian V. Rowe

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Cottages in Shelter Island Heights

Exterior
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
$265 nightly
The price is $301
Dec 7 - Dec 8
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
$397 nightly
The price is $454
Dec 14 - Dec 15
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Exterior
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
$148 nightly
The price is $167
Dec 9 - Dec 10
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Cottage in 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 7 - Dec 8
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Terrace/patio
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in Greenport

10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$457 nightly
The price is $522
Dec 8 - Dec 9
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior
My Humble Abode 2BR Beachside Home | TennisPoolPKG

Cottage in Napeague

10.0 out of 10, Exceptional, (1)
$1,373 nightly
The price is $1,538
Jan 6 - Jan 7, 2026
Total with taxes and fees
My Humble Abode 2BR Beachside Home | TennisPoolPKG
Exterior
Seabreeze #4: Charming Cottage Footsteps to the Beach

Cottage in Hampton Bays

8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$398 nightly
The price is $455
Dec 10 - Dec 11
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach
Exterior
Luxurious 3 BR Cottage w/ Ocean View Balcony

Cottage in Napeague

10.0 out of 10, Exceptional, (3)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
$2,162 nightly
The price is $2,423
Jan 1 - Jan 2, 2026
Total with taxes and fees
Luxurious 3 BR Cottage w/ Ocean View Balcony
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
"We stayed for three nights and no issues at all. Place is well taken care. "
Dominick 3-night trip
Posted 4 days ago
Sleep Inn & Suites Niantic North

Find out more about Shelter Island Heights

Shelter Island Heights Cottages information

Number of reviews
59
Accommodation
213 Cottages
Lowest Price
$301
Highest Price
$2,423

Frequently asked questions

How much do cottages in Shelter Island Heights cost?
Rates for cottages in Shelter Island Heights range between $301 and $2,423 per night. No matter your budget, you'll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Shelter Island Heights?
You can choose from 213 cottages in Shelter Island Heights. Whether you're traveling with the little ones or organizing a weekend escape with your closest amigos, Expedia can help you find the ideal space to enjoy the surrounding nature.
Why book your cottage in Shelter Island Heights with Expedia?
Expedia has some excellent cottages in Shelter Island Heights, so get set for a memorable stay close to nature. If you're on a budget, select how much you're willing to spend and the star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the perfect digs whatever your escape looks like.
How can I find cheap cottages in Shelter Island Heights?
Expedia can help you easily track down cheap cottages in Shelter Island Heights. To book your perfect stay in a few quick keystrokes, try out our handy filter tool to refine your search results by budget, star rating and amenities.
What is there to do in Shelter Island Heights near my cottage?
Once you've unpacked and settled in, head out and explore the cool things Shelter Island Heights has for you to experience. Sylvester Manor is a great attraction to add to your travel itinerary.

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