Shelter Island Heights Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Shelter Island Heights holiday rentals

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 AU$319
includes taxes & fees
3 Apr - 4 Apr
The Anchor at Soundview · Beach+Ocean+Sunrise

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
The price is AU$379
includes taxes & fees
7 Apr - 8 Apr
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$276
includes taxes & fees
14 Apr - 15 Apr
1-bedroom cottage with Grove Beach 🏖️ access.

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 AU$295
includes taxes & fees
7 Apr - 8 Apr
The Stern at Soundview · Beach+Ocean+Sunrise

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, (18 reviews)
"Wonderful place with a great location! Fantastic communication!"
United States
Cary H.
The price is AU$449
includes taxes & fees
7 Apr - 8 Apr
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is AU$284
includes taxes & fees
13 Apr - 14 Apr
Windward Shores Ocean Resort

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is AU$335
includes taxes & fees
5 Apr - 6 Apr
Lakefront Boho Tiny House

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (53 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is AU$302
includes taxes & fees
7 Apr - 8 Apr
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is AU$630
includes taxes & fees
6 Apr - 7 Apr
Rogers Lake House (87) · CT College+Beach+USCGA

Seabreeze 3 Cozy cottage by the beach

Seabreeze 3 Cozy cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is AU$681
includes taxes & fees
13 Apr - 14 Apr
Seabreeze 3 Cozy cottage by the beach

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is AU$363
includes taxes & fees
5 Apr - 6 Apr
Cozy Lakefront Tiny House

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (420 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is AU$240
includes taxes & fees
16 Apr - 17 Apr
Montauk Oceanside Suites

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is AU$898
includes taxes & fees
24 Apr - 25 Apr
Coastal New England Waterfront Home, Harkness Park, Casinos

PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
The price is AU$4,949
includes taxes & fees
7 Apr - 8 Apr
PinkWood PlayHouse

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled
Old Lyme
8.0 out of 10, Very good, (1 review)
"Check in was a nightmare, no code was sent to open the key holder. Got there about 6 PM and still no code, had to contact VRBO directly to get code. Took almost 15 min to open the key lock. It needs to be replaced. Was a big problem as we left as well. Other than that all was good. Was shocked that only 1 nice restaurant in the area, The Hideaway, but they were fantastic and did all they could to make each of our 7 visits there great. Will head back again to this place come summer, food was...
United States
Richard W.
The price is AU$584
includes taxes & fees
5 Apr - 6 Apr
#34- Stunning-Newly Remodeled

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is AU$539
includes taxes & fees
5 Apr - 6 Apr
Floating Nest on Private River. Serene Views & Ultimate Relaxation

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is AU$301
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is AU$280
includes taxes & fees
5 Apr - 6 Apr
North Fork Cottages & RV Resort

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
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.
The price is AU$639
includes taxes & fees
7 Apr - 8 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,309 reviews)
"Great property "
United States
brian
The price is AU$278
includes taxes & fees
16 Apr - 17 Apr
Montauk Manor
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favourite 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 depend 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 AU$240 per night. Entering your travel dates in the search wizard might find you 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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Shelter Island Heights is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Shelter Island Heights?

With 33 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.