Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Shelter Island vacation rentals

Lobby

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1,281 reviews)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
$156 nightly
The price is $178
Jan 29 - Jan 30
Total with taxes and fees
Montauk Manor
On the beach

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
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
$172 nightly
The price is $194
Jan 25 - Jan 26
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1 review)
$397 nightly
The price is $454
Jan 29 - Jan 30
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Smart TV, books

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
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.
$358 nightly
The price is $404
Jan 19 - Jan 20
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, fireplace, books

Vacation Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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.
$323 nightly
The price is $365
Feb 9 - Feb 10
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Beach nearby

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
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.
$308 nightly
The price is $348
Jan 27 - Jan 28
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Interior

Cottage in Waterford

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Cottage was perfect. Immaculate, well equipped, beautifully decorated. It had everything we needed! My family and I loved our stay here and will definitely be back."
United States
Nina B.
$277 nightly
The price is $314
Jan 18 - Jan 19
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Beach nearby, sun loungers, beach towels

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$353 nightly
The price is $399
Jan 16 - Jan 17
Total with taxes and fees
Beach Cottage, private beach and pass
1 bedroom, desk, iron/ironing board, travel crib

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$157 nightly
The price is $178
Jan 21 - Jan 22
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
On the beach

Apartment in Old Lyme

Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.6 out of 10, Exceptional, (8 reviews)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
$172 nightly
The price is $194
Jan 25 - Jan 26
Total with taxes and fees
Freeboard at Soundview · Beach+Ocean+Sunrise
Terrace/patio

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,114 nightly
The price is $1,273
Jan 25 - Jan 26
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
On the beach

Apartment in Old Lyme

The Anchor at Soundview · Beach+Ocean+Sunrise
2.0 star property
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.
$172 nightly
The price is $194
Jan 25 - Jan 26
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, oven, stovetop

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4 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.
$856 nightly
The price is $978
Feb 8 - Feb 9
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Condo in Downtown Montauk

Offshore Residences
4.5 star property
$559 nightly
The price is $639
Jan 18 - Jan 19
Total with taxes and fees
Offshore Residences
Terrace/patio

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$198 nightly
The price is $226
Jan 19 - Jan 20
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Outdoor dining

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (22 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,170 nightly
The price is $1,337
Jan 20 - Jan 21
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$389 nightly
The price is $444
Jan 20 - Jan 21
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach
Beach

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
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.
$433 nightly
The price is $490
Jan 20 - Jan 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

Vacation Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
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.
$384 nightly
The price is $434
Jan 18 - Jan 19
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
On the beach

Apartment in Old Lyme

The Bridge at Soundview · Beach+OceanView+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Great space, large dining area, fully stocked kitchen, large bedrooms, great mattresses, ocean view from deck and one block from the ocean "
United States
Scott F.
$432 nightly
The price is $488
Jan 25 - Jan 26
Total with taxes and fees
The Bridge at Soundview · Beach+OceanView+Sunrise
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"The staff was wonderful and the room and views fantastic."
Cathleen 2-night trip
Posted 4 days ago
The Harbor Front Inn

Find out more about Shelter Island

Everything you need to know about Shelter Island vacation rentals

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

Shelter Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shelter Island rentals

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

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.

Explore a world of travel with Expedia

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?

Summer 2026 Now Available! Grab an amazing property in the heart of the Hamptons: This vacation home near Shelter Island is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 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 patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island?

Choose from 89 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Mashomack Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Crescent Beach 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.