Shelter Island Vacation Rentals

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Our top choices for Shelter Island vacation rentals

US Open Luxury Retreat - 9 Min to Course - sleeps 10

US Open Luxury Retreat - 9 Min to Course - sleeps 10
Hampton Bays
$14,964 nightly
The price is $17,096
May 7 - May 8
Total with taxes and fees
US Open Luxury Retreat - 9 Min to Course - sleeps 10

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
$187 nightly
The price is $214
May 3 - May 4
Total with taxes and fees
North Fork Cottages & RV Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$168 nightly
The price is $190
May 1 - May 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$237 nightly
The price is $268
May 3 - May 4
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (55 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
$240 nightly
The price is $271
May 10 - May 11
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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.
$424 nightly
The price is $478
May 6 - May 7
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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, (22 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.
$296 nightly
The price is $335
May 3 - May 4
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,334 reviews)
"Incredible place to stay "
United States
melissa
$168 nightly
The price is $192
May 18 - May 19
Total with taxes and fees
Montauk Manor

Seabreeze #4 Charming Cottage just 2.5 miles to US Open

Seabreeze #4 Charming Cottage just 2.5 miles to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$576 nightly
The price is $620
May 4 - May 5
Total with taxes and fees
Seabreeze #4 Charming Cottage just 2.5 miles to US Open

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
$283 nightly
The price is $323
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
$183 nightly
The price is $209
May 3 - May 4
Total with taxes and fees
Windward Shores Ocean Resort

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 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.
$364 nightly
The price is $411
May 5 - May 6
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$283 nightly
The price is $323
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

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
$429 nightly
The price is $484
May 5 - May 6
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
$224 nightly
The price is $256
May 11 - May 12
Total with taxes and fees
Cliffside Resort Condominiums

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$295 nightly
The price is $337
May 21 - May 22
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

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
$255 nightly
The price is $288
May 3 - May 4
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
$174 nightly
The price is $199
May 12 - May 13
Total with taxes and fees
Montauk Oceanside Suites

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
$184 nightly
The price is $211
May 17 - May 18
Total with taxes and fees
Driftwood Resort
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 $190 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home rental near Shelter Island offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island?

Choose from 89 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Mashomack Preserve 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 Crescent Beach 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.