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Shelter Island Heights Holiday Rentals

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Our top choices for Shelter Island Heights holiday rentals

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1276)
"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
The price is NZ$306
includes taxes & fees
29 Jan - 30 Jan 2026
Montauk Manor

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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.
The price is NZ$12,613
includes taxes & fees
5 Jan - 6 Jan 2026
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NZ$769
includes taxes & fees
12 Jan - 13 Jan 2026
Seabreeze #3: Cozy Cottage by the beach

The Bridge at Soundview · Beach+OceanView+Sunrise

The Bridge at Soundview · Beach+OceanView+Sunrise
2.0 star property
Old Lyme
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.
The price is NZ$840
includes taxes & fees
6 Jan - 7 Jan 2026
The Bridge at Soundview · Beach+OceanView+Sunrise

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)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is NZ$637
includes taxes & fees
5 Jan - 6 Jan 2026
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
East Lyme
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.
The price is NZ$630
includes taxes & fees
8 Jan - 9 Jan 2026
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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)
"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 NZ$695
includes taxes & fees
11 Jan - 12 Jan 2026
Rogers Lake House (87) · CT College+Beach+USCGA

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
Waterford
10.0 out of 10, Exceptional, (14)
"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.
The price is NZ$539
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is NZ$317
includes taxes & fees
10 Jan - 11 Jan 2026
1-bedroom cottage with Grove Beach 🏖️ access.

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is NZ$366
includes taxes & fees
6 Jan - 7 Jan 2026
Lakefront Boho Tiny House

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
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.
The price is NZ$366
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Lakefront Tiny House

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$763
includes taxes & fees
5 Jan - 6 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is NZ$795
includes taxes & fees
14 Jan - 15 Jan 2026
Beach Cottage, private beach and pass

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)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$754
includes taxes & fees
1 Jan - 2 Jan 2026
Adorable Cottage, 5 min walk to water & town

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is NZ$2,198
includes taxes & fees
5 Jan - 6 Jan 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
10.0 out of 10, Exceptional, (3)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is NZ$894
includes taxes & fees
11 Jan - 12 Jan 2026
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

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, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is NZ$2,308
includes taxes & fees
4 Jan - 5 Jan 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is NZ$1,142
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Residences

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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.
The price is NZ$896
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Shoreline Oasis

Shoreline Oasis
Clinton
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.
The price is NZ$445
includes taxes & fees
1 Jan - 2 Jan 2026
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

Find out more about Shelter Island Heights

Everything you need to know about Shelter Island Heights holiday rentals

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

Shelter Island Heights holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island Heights holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island Heights holiday rentals we have selected for you start as low as NZ$306 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Shelter Island Heights?

Yes, there are holiday rentals close to the most popular sights in Shelter Island Heights, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shelter Island Heights has to offer?

Stunning Hampton Holiday Family Fantasy for your Team : This holiday home rental outside of Shelter Island Heights is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island Heights?

With 34 Expedia holiday rentals, you're guaranteed 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 holiday rental in Shelter Island Heights like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shelter Island Heights. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.