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Shelter Island Holiday Rentals

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Our top choices for Shelter Island holiday rentals

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$515
includes taxes & fees
27 July - 28 July
1-bedroom cottage with Grove Beach 🏖️ access.

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
"Great stay & great staff!"
United States
James
The price is NZ$698
includes taxes & fees
29 July - 30 July
North Fork Resort

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

Rogers Lake House (87) · 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.
The price is NZ$925
includes taxes & fees
5 July - 6 July
Rogers Lake House (87) · CT College+Beach+USCGA

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
The price is NZ$567
includes taxes & fees
5 July - 6 July
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · 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
The price is NZ$552
includes taxes & fees
5 July - 6 July
The Stern at Soundview · Beach+Ocean+Sunrise

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.
The price is NZ$799
includes taxes & fees
8 July - 9 July
Seabreeze 4 Charming Cottage footsteps to beach

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.
The price is NZ$1,146
includes taxes & fees
8 July - 9 July
Beach Cottage, private beach and pass

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is NZ$571
includes taxes & fees
8 July - 9 July
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · 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.
The price is NZ$951
includes taxes & fees
7 July - 8 July
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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.
The price is NZ$1,046
includes taxes & fees
7 July - 8 July
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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
The price is NZ$630
includes taxes & fees
7 July - 8 July
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

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
The price is NZ$601
includes taxes & fees
7 July - 8 July
Keel at Soundview · Beach+OceanView+Sunrise

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Old Lyme
The price is NZ$364
includes taxes & fees
5 July - 6 July
Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

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.
The price is NZ$974
includes taxes & fees
22 July - 23 July
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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
The price is NZ$578
includes taxes & fees
5 July - 6 July
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
The price is NZ$641
includes taxes & fees
7 July - 8 July
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (5 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.
The price is NZ$2,024
includes taxes & fees
6 July - 7 July
BlackBerry Private home with jacuzzi yearlong

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (264 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is NZ$980
includes taxes & fees
21 July - 22 July
Cliffside Resort Condominiums

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is NZ$1,371
includes taxes & fees
22 July - 23 July
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$1,267
includes taxes & fees
7 July - 8 July
Beachside Bliss w/ Game Room, Gym & Golf Green
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shelter Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as NZ$515 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island holiday 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 holiday.

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 holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Shelter Island has to offer?

Exquisite New Hampton Home in a Perfect Location: This holiday home rental outside of Shelter Island is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Shelter Island?

Choose from 90 Expedia holiday rentals in Shelter Island for a memorable holiday.

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 holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.