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Search the Best Cabins in Shelter Island

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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

Exterior
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (83)
"Nice decoration, clean amenities, good stay"
United States
weihao
$166 nightly
The price is $190
Jan 4 - Jan 5, 2026
Total with taxes and fees
Offshore Montauk
Front of property
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (879)
"Really clean and nice location"
United States
Tiara
$120 nightly
The price is $138
Jan 4 - Jan 5, 2026
Total with taxes and fees
Kenny's Tipperary Inn
Front of property - evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1270)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
$156 nightly
The price is $178
Jan 5 - Jan 6, 2026
Total with taxes and fees
Montauk Manor
Property entrance
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (128)
"Great location. Nice and clean room and property"
United States
Eric
$99 nightly
The price is $114
Dec 23 - Dec 24
Total with taxes and fees
The Niantic Inn
Exterior
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1005)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
$69 nightly
The price is $79
Dec 28 - Dec 29
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Exterior detail
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (461)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveler
$67 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
House on Chase Creek
Exterior
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 22 - Dec 23
Total with taxes and fees
Clinton Motel
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very Good, (710)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
$92 nightly
The price is $105
Dec 22 - Dec 23
Total with taxes and fees
Shorewood Inn
Property entrance
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
$178 nightly
The price is $203
Jan 21 - Jan 22, 2026
Total with taxes and fees
The Harbor Front Inn
Property grounds
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$127 nightly
The price is $142
Dec 22 - Dec 23
Total with taxes and fees
Hamlet Inn
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
$387 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Exterior
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
$110 nightly
The price is $126
Jan 12 - Jan 13, 2026
Total with taxes and fees
Hyatt Place Long Island East End
Exterior
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"The staff was friendly. The room was good. "
United States
Narida
$101 nightly
The price is $116
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Exterior
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.2 out of 10, Good, (69)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
$121 nightly
The price is $138
Dec 24 - Dec 25
Total with taxes and fees
Hampton Bays Hotel on Main
Lunch, dinner, brunch served; American cuisine, beach views
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (599)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$186 nightly
The price is $213
Jan 8 - Jan 9, 2026
Total with taxes and fees
Sound View Greenport
Front of property
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, (230)
"Great stay, will definitely go again"
United States
ANTONIO J
$174 nightly
The price is $199
Jan 20 - Jan 21, 2026
Total with taxes and fees
The Shoals Suites and Slips
Exterior
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
$319 nightly
The price is $361
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Exterior
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
$126 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Bentley Hotel Southampton
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

Montauk Manor

Montauk Manor

10/10 Excellent
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
Kathleen 1-night trip
Posted 6 days ago
Montauk Manor

Find out more about Shelter Island

Shelter Island Cabin Rentals information

Number of reviews
9,207
Accommodation
3 Cabin Rentals
Lowest Price
$77
Highest Price
$442

Frequently asked questions

What are the best cabins near Shelter Island?
Choose one of our 36 cabins in Shelter Island and you'll be rewarded with striking scenery, outdoor fun and memories to treasure. Rustic Lakeside Cabin At White Gate Farm offers a more leisurely pace of life. Treehouse - Countryside - Farm Animals is another great choice if you're craving time out in Mother Nature.
Are there cheap cabins near Shelter Island?
Whether you want to stay near the water or on the top of a mountain, we've got a great selection of cheap cabins near Shelter Island to suit your budget and taste. Priced from $77 to $442 a night, your ideal cabin rental is waiting here.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.
What are the best mountain cabins near Shelter Island?
Stay in a mountain cabin near Shelter Island and treat yourself to wondrous views, outdoor activities and an experience that's hard to forget. Rustic Lakeside Cabin At White Gate Farm is a standout. Nestled high in the hills, you'll find amenities like a microwave oven and a kitchen here. Mohegan Cabin Estate is another popular option. It comes with winery tours, a microwave oven and stunning natural surroundings.
What are the best pet-friendly cabins near Shelter Island?
Pack up your pooch's favorite toy and head for a pet-friendly cabin near Shelter Island. Leading the pack is Rustic Lakeside Cabin At White Gate Farm. With useful amenities like children's activities and on-site watersports, you and your furry pal will enjoy a stay worth howling about. Snoopy can also come along for the journey at Remote Long Island Lakefront Cabin W. This getaway features a deck, a queen bed and more.
What are the best cabins with pools near Shelter Island?
Don your swimsuit and enjoy a refreshing dip whenever you want when you opt for one of our cabin rentals with a pool near Shelter Island. Cabin - Water Mill Wooded Escape ranks high among travelers. A swimming pool and fitness facilities are among the other amenities that await you here. Or, take some time out at Spacious And New Deluxe Cabin In Family Campground In Northeastern Ct. As well as a pleasant pool, this cabin comes with on-site watersports and a swimming pool.
Can I find beach cabins near Shelter Island?
Get a big dose of sunshine and salty air at Rustic Lakeside Cabin At White Gate Farm. One of our leading Shelter Island beach cabin rentals, it comes with on-site watersports and beach sun loungers. You can also spend easygoing days by the sea at Lagoon Lodge: North Fork, Charming 3br. Clothes washing facilities and children's activities will help make your break extra special.
What are the best weekend cabin rentals in Shelter Island?
Whether you're organizing a quick trip with your sweetheart or your entire family, we'll help you locate the ideal weekend cabin getaway. One awesome option? Rustic Lakeside Cabin At White Gate Farm. Featuring on-site watersports and a private beach, you'll appreciate being close to nature here. Remote Long Island Lakefront Cabin W is another fantastic place where you can hit pause on life. Spend a couple of nights at this retreat which offers a patio and a fireplace.
What are the best cabin prices near Shelter Island?
Whether you're traveling on a budget or want to splurge on your next getaway, you'll find what you're looking for with Expedia. At the moment, you can score a Shelter Island cabin from as little as $77 per night.
Can I find log cabins in Shelter Island?
Begin your day with a piping hot coffee in your cozy log cabin and then spend hours fishing and shore fishing. Sound perfect to you? Then head for The Retreat Log Cabin. Another wooden escape featuring ample warmth and charm is Log Cabin, 5 Min To Casino With Pond. Activities like canoeing and snowboarding will add to your experience here.
What are the highest-rated cabins in Shelter Island?
Expedia travelers can't get enough of Remote Long Island Lakefront Cabin W. This excellent option features a host of useful amenities including a patio and a fireplace. It won't take you very long to see why Treehouse - Countryside - Farm Animals is also a hit with vacationers. Conveniences like a patio and a fireplace will help make your stay even more memorable.
Why should I book a cabin near Shelter Island?
For a nature-filled escape at a great price, you can't beat a cabin. Visualize yourself waking up to the sounds of chirping birds and having breakfast on your deck surrounded by beautiful vistas. Lock in a cabin near Shelter Island and say "see ya" to the hectic pace of the city. Whether they're up a mountain or down by the beach, cabins offer a relaxing, rustic experience for anyone needing a break.

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