Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Shelter Island vacation rentals

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, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is ￥26,304
￥61,619 total
includes taxes & fees
Feb 25 - Feb 26
Beach Cottage, private beach and pass
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, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥12,387
￥27,831 total
includes taxes & fees
Feb 25 - Feb 26
1-bedroom cottage with Grove Beach 🏖️ access.
Beach nearby

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 ￥13,924
￥32,529 total
includes taxes & fees
Feb 25 - Feb 26
The Anchor at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, oven, stovetop

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is ￥19,763
￥40,395 total
includes taxes & fees
Mar 2 - Mar 3
The gardners Cottage 1 mile from long Island Sound - pet friendly
Smart TV, fireplace, books

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 ￥18,308
￥60,359 total
includes taxes & fees
Feb 25 - Feb 26
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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, (16 reviews)
"Convenient location. The property had everything we needed for a one-night stay. "
United States
Jane E.
The price is ￥21,155
￥47,215 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is ￥21,696
￥72,590 total
includes taxes & fees
Feb 25 - Feb 26
Rogers Lake House (87) · CT College+Beach+USCGA
Terrace/patio

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (76 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is ￥41,753
￥54,240 total
includes taxes & fees
Feb 28 - Mar 1
Cottage on Beach front Estate with Dockage .Walk to Village
Terrace/patio

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥19,330
￥191,695 total
includes taxes & fees
Feb 25 - Feb 26
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (306 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 ￥20,375
￥27,483 total
includes taxes & fees
Feb 26 - Feb 27
Windward Shores Ocean Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,297 reviews)
"Nice pool, great restaurant "
United States
April
The price is ￥28,253
￥35,308 total
includes taxes & fees
Feb 28 - Mar 1
Montauk Manor
Dining

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, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is ￥16,856
￥76,485 total
includes taxes & fees
Mar 4 - Mar 5
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Exterior

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Southold
The price is ￥25,361
￥68,198 total
includes taxes & fees
Mar 3 - Mar 4
Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Interior

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is ￥34,794
￥58,067 total
includes taxes & fees
Mar 25 - Mar 26
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Exterior

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, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is ￥35,389
￥75,569 total
includes taxes & fees
Feb 25 - Feb 26
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Property grounds

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is ￥27,835
￥55,825 total
includes taxes & fees
Feb 25 - Feb 26
Stylish Modern Stay Steps from the Ocean
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 ￥13,924
￥32,529 total
includes taxes & fees
Feb 26 - Feb 27
The Stern at Soundview · Beach+Ocean+Sunrise
Terrace/patio

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 ￥18,402
￥30,920 total
includes taxes & fees
Feb 25 - Feb 26
American Beech in Greenport - Petite King Room 7
2 bedrooms, desk, iron/ironing board, travel crib

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is ￥20,898
￥59,615 total
includes taxes & fees
Feb 25 - Feb 26
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Terrace/patio

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥15,309
￥206,712 total
includes taxes & fees
Feb 25 - Feb 26
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question. "
Andrew 2-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex

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:

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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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This vacation home rental near Shelter Island is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 88 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.