Shelter Island Holiday Rentals

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Our top choices for Shelter Island holiday rentals

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled
Old Lyme
#34- Stunning-Newly Remodeled

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (38 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$260
includes taxes & fees
9 Mar - 10 Mar
1-bedroom cottage with Grove Beach 🏖️ access.

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is AU$683
includes taxes & fees
8 Mar - 9 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,299 reviews)
"Nice pool, great restaurant "
United States
April
The price is AU$274
includes taxes & fees
30 Mar - 31 Mar
Montauk Manor

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
The price is AU$349
includes taxes & fees
28 Mar - 29 Mar
The Stern at Soundview · Beach+Ocean+Sunrise

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 AU$409
includes taxes & fees
8 Mar - 9 Mar
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (309 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is AU$271
includes taxes & fees
8 Mar - 9 Mar
Windward Shores Ocean Resort

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, (16 reviews)
"Convenient location. The property had everything we needed for a one-night stay. "
United States
Jane E.
The price is AU$436
includes taxes & fees
8 Mar - 9 Mar
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is AU$7,572
includes taxes & fees
19 Mar - 20 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$286
includes taxes & fees
8 Mar - 9 Mar
American Beech in Greenport - Petite King Room 7

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)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AU$611
includes taxes & fees
12 Mar - 13 Mar
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is AU$415
includes taxes & fees
8 Mar - 9 Mar
Hamptons apartment getaway

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is AU$944
includes taxes & fees
8 Mar - 9 Mar
Offshore Residences

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is AU$520
includes taxes & fees
21 Mar - 22 Mar
Floating Nest on Private River. Serene Views & Ultimate Relaxation

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
United States
Katy C.
The price is AU$652
includes taxes & fees
8 Mar - 9 Mar
Rogers Lake House (87) · CT College+Beach+USCGA

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
The price is AU$397
includes taxes & fees
1 Apr - 2 Apr
North Fork Cottages & RV Resort

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
East Hampton North
The price is AU$955
includes taxes & fees
15 Mar - 16 Mar
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is AU$355
includes taxes & fees
1 Apr - 2 Apr
The Anchor at Soundview · Beach+Ocean+Sunrise

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.
The price is AU$714
includes taxes & fees
1 Apr - 2 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is AU$2,714
includes taxes & fees
19 Mar - 20 Mar
Cozy 5 Bedroom With Wi-fi And Air Condition
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 favourite 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 depend 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 AU$237 per night. Entering your travel dates in the search wizard might find you 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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Shelter Island is located on the beach, and has a fireplace, a patio 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island?

Choose from 89 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. Mashomack Preserve and Crescent Beach 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.