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Shelter Island Heights Vacation Rentals

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Shelter Island Heights vacation rentals

Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1270)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
$156 nightly
The price is $178
Jan 5 - Jan 6, 2026
Total with taxes and fees
Montauk Manor
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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.
$6,469 nightly
The price is $7,391
Jan 5 - Jan 6, 2026
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
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
$172 nightly
The price is $195
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
$184 nightly
The price is $208
Jan 6 - Jan 7, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
$320 nightly
The price is $362
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
$178 nightly
The price is $201
Dec 23 - Dec 24
Total with taxes and fees
Lakefront Boho Tiny House
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1)
$387 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Exterior
Cozy Lakefront Tiny House

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
$193 nightly
The price is $218
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cozy Lakefront Tiny House
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5)
"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.
$356 nightly
The price is $403
Jan 21 - Jan 22, 2026
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
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.
$325 nightly
The price is $367
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

Vacation Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.
$5,636 nightly
The price is $6,439
Dec 27 - Dec 28
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Front of property
Canoe Place Waterfront Residences

Condo in Hampton Bays

Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
$2,009 nightly
The price is $2,296
Dec 24 - Dec 25
Total with taxes and fees
Canoe Place Waterfront Residences
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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, (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.
$277 nightly
The price is $314
Jan 13 - Jan 14, 2026
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Pool
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views

Villa in New London

Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views
10.0 out of 10, Exceptional, (45)
"Great location. Nice outdoor space and plenty of room for large group. Clean and thoughtful amenities."
United States
Beth N.
$1,573 nightly
The price is $1,780
Dec 23 - Dec 24
Total with taxes and fees
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

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)
"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
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
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.
$799 nightly
The price is $913
Jan 4 - Jan 5, 2026
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

Beachside Bliss w/ Game Room, Gym & Golf Green
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.
$458 nightly
The price is $518
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,085 nightly
The price is $1,240
Dec 23 - Dec 24
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Anchor at Soundview · Beach+Ocean+Sunrise
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.
$173 nightly
The price is $196
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise
Exterior
Shoreline Oasis

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
$229 nightly
The price is $260
Dec 23 - Dec 24
Total with taxes and fees
Shoreline Oasis
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 Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything was wonderful. Staff was friendly, very clean,we enjoyed it."
Donna 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

Find out more about Shelter Island Heights

Everything you need to know about Shelter Island Heights 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 Heights 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 Heights vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island Heights vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island Heights. 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 Heights 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 Heights rentals

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

Are there vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Shelter Island Heights. Make sure you have time to check out the golf courses and entertainment choices during your trip.

What's the top vacation rental that Shelter Island Heights has to offer?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : Visitors like this Shelter Island Heights vacation home rental. It 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 Heights?

With 34 Expedia vacation rentals, you're sure to find just the right place for your Shelter Island Heights stay.

What’s there to see and do in Shelter Island Heights?

Sunset Beach and Crescent Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shelter Island Country Club and Sylvester Manor.

What’s a vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.