Shelter Island Vacation Rentals

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Our top choices for Shelter Island vacation rentals

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
$1,145 nightly
The price is $1,308
Apr 19 - Apr 20
Total with taxes and fees
Work and Play Special! Extended Stay Discount

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
$332 nightly
The price is $376
Apr 18 - Apr 19
Total with taxes and fees
Floating Nest on Private River. Serene Views & Ultimate Relaxation

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$162 nightly
The price is $183
Apr 27 - Apr 28
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
$295 nightly
The price is $333
Apr 22 - Apr 23
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
$186 nightly
The price is $213
Apr 19 - Apr 20
Total with taxes and fees
North Fork Cottages & RV Resort

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
$240 nightly
The price is $271
Apr 26 - Apr 27
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
$221 nightly
The price is $250
Apr 20 - Apr 21
Total with taxes and fees
Freeboard at Soundview · Beach+Ocean+Sunrise

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,324 reviews)
"Great property "
United States
brian
$168 nightly
The price is $192
Apr 20 - Apr 21
Total with taxes and fees
Montauk Manor

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
$394 nightly
The price is $445
Apr 21 - Apr 22
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$428 nightly
The price is $484
May 14 - May 15
Total with taxes and fees
Beach Cottage, private beach and pass

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
$198 nightly
The price is $226
Apr 29 - Apr 30
Total with taxes and fees
Cliffside Resort Condominiums

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
$172 nightly
The price is $197
Apr 19 - Apr 20
Total with taxes and fees
Windward Shores Ocean Resort

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 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
$448 nightly
The price is $506
May 12 - May 13
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
$379 nightly
The price is $428
Apr 21 - Apr 22
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Seabreeze 3 Cozy cottage by the beach

Seabreeze 3 Cozy cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$453 nightly
The price is $484
Apr 26 - Apr 27
Total with taxes and fees
Seabreeze 3 Cozy cottage by the beach

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
$161 nightly
The price is $184
Apr 21 - Apr 22
Total with taxes and fees
Montauk Oceanside Suites

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
$239 nightly
The price is $270
Apr 20 - Apr 21
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
BlackBerry Private home with jacuzzi yearlong

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
$235 nightly
The price is $266
Apr 26 - Apr 27
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
$215 nightly
The price is $246
May 11 - May 12
Total with taxes and fees
The Surf Club
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

Find out more about Shelter Island

Everything you need to know about Shelter Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $183 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation home rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island?

Choose from 88 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.