Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
$156 nightly
The price is $178
Dec 22 - Dec 23
Total with taxes and fees
Montauk Manor
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Dec 7 - Dec 8
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
$356 nightly
The price is $403
Dec 7 - Dec 8
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Vacation Home in Waterford

10.0 out of 10, Exceptional, (10)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
$319 nightly
The price is $361
Dec 18 - Dec 19
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
$397 nightly
The price is $454
Dec 14 - Dec 15
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
$148 nightly
The price is $167
Dec 9 - Dec 10
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
$265 nightly
The price is $301
Dec 7 - Dec 8
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

2.0 star property
9.0 out of 10, Wonderful, (4)
"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.
$323 nightly
The price is $365
Dec 7 - Dec 8
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in Water Mill

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,353 nightly
The price is $7,259
Dec 8 - Dec 9
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

9.6 out of 10, Exceptional, (13)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

9.0 out of 10, Wonderful, (4)
"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.
$771 nightly
The price is $881
Dec 15 - Dec 16
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$430 nightly
The price is $486
Dec 9 - Dec 10
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
8.0 out of 10, Very Good, (2)
"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.
$171 nightly
The price is $193
Dec 7 - Dec 8
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, stovetop, dishwasher
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in Greenport

10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$457 nightly
The price is $522
Dec 8 - Dec 9
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Cottage in Old Saybrook Center

9.6 out of 10, Exceptional, (39)
"Great property, would stay here again."
United States
charles b.
$450 nightly
The price is $509
Dec 7 - Dec 8
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Private kitchen
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

10.0 out of 10, Exceptional, (1)
"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.
$298 nightly
The price is $337
Dec 6 - Dec 7
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$368 nightly
The price is $416
Dec 7 - Dec 8
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
$432 nightly
The price is $488
Dec 6 - Dec 7
Total with taxes and fees
The Bridge at Soundview · Beach+OceanView+Sunrise
Front of property
Canoe Place Waterfront Residences

Condo in Hampton Bays

4.0 star property
10.0 out of 10, Exceptional, (1)
$1,819 nightly
The price is $2,079
Dec 28 - Dec 29
Total with taxes and fees
Canoe Place Waterfront Residences
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
"A welcoming place with some nice touches."
Leslie 1-night trip
Posted 4 days ago
Pier Blue Inn Old Saybrook - Essex

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.

How many vacation rentals are there in Shelter Island?

Choose from 85 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. Shelter Island Historical Society and Crescent Beach 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.