Shelter Island Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Shelter Island holiday rentals

1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (43 reviews)
"The host was very accommodating and very responsive. The cottage was very clean and tidy. "
United States
Rob C.
The price is HK$649
HK$1,435 total
includes taxes & fees
1 Jun - 2 Jun
1-bedroom cottage with Grove Beach 🏖️ access.
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,327
HK$2,659 total
includes taxes & fees
15 Jun - 16 Jun
North Fork Resort
Smart TV, books

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
The price is HK$1,212
HK$3,839 total
includes taxes & fees
4 Jun - 5 Jun
Rogers Lake House (87) · CT College+Beach+USCGA
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,516
HK$2,332 total
includes taxes & fees
2 Jun - 3 Jun
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Beach nearby

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 HK$1,040
HK$2,071 total
includes taxes & fees
1 Jun - 2 Jun
The Stern at Soundview · Beach+Ocean+Sunrise
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,298
HK$3,166 total
includes taxes & fees
2 Jun - 3 Jun
Adorable Cottage, 5 min walk to water & town
Beach nearby

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.
The price is HK$1,262
HK$3,301 total
includes taxes & fees
1 Jun - 2 Jun
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV, offices

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)
The price is HK$1,034
HK$4,096 total
includes taxes & fees
31 May - 1 Jun
Seabreeze #3 Cozy Cottage steps to the beach
Beach nearby

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 HK$1,151
HK$2,213 total
includes taxes & fees
1 Jun - 2 Jun
Keel at Soundview · Beach+OceanView+Sunrise
1 bedroom, bed sheets

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 HK$1,516
HK$2,332 total
includes taxes & fees
31 May - 1 Jun
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (57 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is HK$1,411
HK$2,828 total
includes taxes & fees
15 Jun - 16 Jun
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Interior

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.
The price is HK$2,053
HK$3,670 total
includes taxes & fees
10 Jun - 11 Jun
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"Beautiful property! Just four houses from the beach and a beachfront restaurant. Very comfortable living areas. Well appointed kitchen with in unit washer and dryer. Host was prompt and clear with all communication. Off street parking with room for three vehicles. Too cold to use the outside lounging areas, but they look very nice as well. "
United States
Tim M.
#35 - Beautiful 3 BR Beach Haven
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,524
HK$2,082 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
Dining

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (1 review)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is HK$1,340
HK$2,758 total
includes taxes & fees
1 Jun - 2 Jun
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,355 reviews)
"Had a wonderful stay"
United States
Meghan
Montauk Manor
Beach nearby, sun-loungers, beach towels

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.
The price is HK$3,048
HK$5,421 total
includes taxes & fees
3 Jun - 4 Jun
Beach Cottage, private beach and pass
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is HK$1,484
HK$1,951 total
includes taxes & fees
4 Jun - 5 Jun
Driftwood Resort
Beach nearby

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 HK$798
HK$2,320 total
includes taxes & fees
1 Jun - 2 Jun
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Smart TV

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
Waterford
10.0 out of 10, Exceptional, (5 reviews)
"Great location and extremely clean. I would definitely recommend and stay again. "
United States
Zach S.
The price is HK$1,594
HK$3,833 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street
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

The Shoals Suites and Slips

The Shoals Suites and Slips

8/10 Good
"The room and balcony were both clean and spacious. No major complaints - just that blackout curtains don't exist on the larger windows, which can be an acquired taste for some. We went over Memorial Day weekend, which is typically the onset of beach season, and had wanted to use the beach passes they advertise as part of the resort amenities, to park at various local beaches for our strolls. But at check-in, they said they had not ordered them yet for the 2026 season, so that was a letdown. Also, the buffet breakfast we thought the resort would provide onsite turned out to be just (2) $10 vouchers/night to Stone Street Cafe a 4-min drive away. Street parking is easy there, but just a juice at the cafe was already $10. A shout-out to Mario at the front desk though - he was responsive and prompt to answer all our questions. He was both kind and patient - a wonderful asset to Shoals."
Deborah 2-night trip
Posted 1 hour ago
The Shoals Suites and Slips

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

Look no further and take a look at our great range of rental properties in Shelter Island!

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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Shelter Island offers an outdoor pool, a patio and a BBQ 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 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 90 Expedia holiday rentals in Shelter Island for a memorable holiday.

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. Mashomack Preserve and Gardiner's Bay Country Club 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.