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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, (55 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
$1,371 nightly
The price is $1,566
Jul 20 - Jul 21
Total with taxes and fees
Work and Play Special! Extended Stay Discount

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
$260 nightly
The price is $298
Jul 14 - Jul 15
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
$285 nightly
The price is $326
Jul 19 - Jul 20
Total with taxes and fees
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Comfortable bed and beautiful surroundings"
United States
Matthew
$260 nightly
The price is $298
Jul 14 - Jul 15
Total with taxes and fees
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

1-bedroom cottage with Grove Beach ๐Ÿ–๏ธ access.

1-bedroom cottage with Grove Beach ๐Ÿ–๏ธ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
$233 nightly
The price is $264
Jul 21 - Jul 22
Total with taxes and fees
1-bedroom cottage with Grove Beach ๐Ÿ–๏ธ access.

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$260 nightly
The price is $298
Jul 14 - Jul 15
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$824 nightly
The price is $893
Jul 21 - Jul 22
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
$319 nightly
The price is $361
Jul 15 - Jul 16
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
$363 nightly
The price is $415
Jul 26 - Jul 27
Total with taxes and fees
North Fork Resort

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

Rogers Lake House (87) ยท CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
$456 nightly
The price is $515
Jul 16 - Jul 17
Total with taxes and fees
Rogers Lake House (87) ยท CT College+Beach+USCGA

The Stern at Soundview ยท Beach+Ocean+Sunrise

The Stern at Soundview ยท Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$254 nightly
The price is $287
Jul 14 - Jul 15
Total with taxes and fees
The Stern at Soundview ยท Beach+Ocean+Sunrise

Keel at Soundview ยท Beach+OceanView+Sunrise

Keel at Soundview ยท Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (2 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
$286 nightly
The price is $323
Jul 15 - Jul 16
Total with taxes and fees
Keel at Soundview ยท Beach+OceanView+Sunrise

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, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
$465 nightly
The price is $525
Jul 14 - Jul 15
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Bay Cottage ยท Rocky Neck Park, Beach & Niantic

The Bay Cottage ยท Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 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.
$453 nightly
The price is $511
Jul 14 - Jul 15
Total with taxes and fees
The Bay Cottage ยท Rocky Neck Park, Beach & Niantic

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
$626 nightly
The price is $708
Jul 14 - Jul 15
Total with taxes and fees
Beach Cottage, private beach and pass

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
$2,928 nightly
The price is $3,180
Jul 21 - Jul 22
Total with taxes and fees
Black Swan Beachfront Home with Jacuzzi year round

Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$817 nightly
The price is $885
Jul 20 - Jul 21
Total with taxes and fees
Seabreeze 4 Charming Cottage footsteps to beach

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, (28 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
$470 nightly
The price is $532
Jul 19 - Jul 20
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Bridgehampton
9.6 out of 10, Exceptional, (16 reviews)
"Great location very quiet "
United States
nancy m.
$458 nightly
The price is $523
Jul 16 - Jul 17
Total with taxes and fees
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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 youโ€™re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, weโ€™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 โ€ฆand on.

Thereโ€™s just as wide a choice of amenities, too. Maybe youโ€™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 youโ€™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 $264 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. Youโ€™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 wantโ€”and just like that, youโ€™ve built your dream Shelter Island vacation.

If youโ€™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.

Explore a world of travel with Expedia

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 90 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Wades Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Mashomack Preserve 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.