Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Shelter Island vacation rentals

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

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 ￥14,048
￥30,147 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥43,624
￥49,840 total
includes taxes & fees
Jun 15 - Jun 16
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 ￥19,089
￥70,880 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥30,808
￥47,391 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥20,116
￥40,759 total
includes taxes & fees
Jun 3 - Jun 4
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 ￥26,375
￥64,813 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥23,194
￥63,956 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥21,024
￥83,244 total
includes taxes & fees
Jun 3 - Jun 4
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 ￥21,347
￥42,807 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥30,808
￥47,391 total
includes taxes & fees
Jun 2 - Jun 3
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, (58 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is ￥25,802
￥53,857 total
includes taxes & fees
Jun 15 - Jun 16
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, (23 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 ￥32,396
￥62,579 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Hair dryer

#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
Condo | 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 ￥39,387
￥51,920 total
includes taxes & fees
Jun 3 - Jun 4
Cliffside Resort Condominiums
Shower, towels, soap, toilet paper

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.
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
The price is ￥60,491
￥72,230 total
includes taxes & fees
Jun 18 - Jun 19
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 ￥61,956
￥110,167 total
includes taxes & fees
Jun 3 - Jun 4
Beach Cottage, private beach and pass
Apartment | 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 ￥30,161
￥39,647 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥14,369
￥44,731 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥31,822
￥77,249 total
includes taxes & fees
Jun 9 - Jun 10
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

Zey Hotel

Zey Hotel

10/10 Excellent
"The garden/lobby/playrooms/boardgames.. bruuuhhh can’t sleep? Just playing there boardgames w family or couple.. travel alone? They have bunch of magazines and books"
Metta 1-night trip
Posted 22 hours ago
Zey Hotel

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

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

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 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.