Holiday Rentals in Shelter Island Heights

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Our top choices for Shelter Island Heights holiday rentals

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is €340
includes taxes & fees
23 Feb - 24 Feb
Beach Cottage, private beach and pass

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 €214
includes taxes & fees
24 Feb - 25 Feb
Cozy Lakefront Tiny House

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is €222
includes taxes & fees
2 Mar - 3 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly

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 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €334
includes taxes & fees
23 Feb - 24 Feb
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is €157
includes taxes & fees
23 Feb - 24 Feb
1-bedroom cottage with Grove Beach 🏖️ access.

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, (16 reviews)
"Convenient location. The property had everything we needed for a one-night stay. "
United States
Jane E.
The price is €256
includes taxes & fees
23 Feb - 24 Feb
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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 €201
includes taxes & fees
26 Feb - 27 Feb
The Stern at Soundview · Beach+Ocean+Sunrise

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 €203
includes taxes & fees
23 Feb - 24 Feb
Lakefront Boho Tiny House

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (306 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is €151
includes taxes & fees
25 Feb - 26 Feb
Windward Shores Ocean Resort

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is €695
includes taxes & fees
23 Feb - 24 Feb
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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 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.
The price is €398
includes taxes & fees
24 Feb - 25 Feb
Rogers Lake House (87) · CT College+Beach+USCGA

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,297 reviews)
"Nice pool, great restaurant "
United States
April
The price is €194
includes taxes & fees
28 Feb - 1 Mar
Montauk Manor

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is €1,053
includes taxes & fees
25 Feb - 26 Feb
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!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is €415
includes taxes & fees
25 Feb - 26 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (76 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is €297
includes taxes & fees
28 Feb - 1 Mar
Cottage on Beach front Estate with Dockage .Walk to Village

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is €410
includes taxes & fees
23 Feb - 24 Feb
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is €313
includes taxes & fees
21 Mar - 22 Mar
Floating Nest on Private River. Serene Views & Ultimate Relaxation

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €173
includes taxes & fees
24 Feb - 25 Feb
American Beech in Greenport - Petite King Room 7

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Southold
The price is €381
includes taxes & fees
1 Mar - 2 Mar
Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
The price is €337
includes taxes & fees
24 Feb - 25 Feb
Direct Lakefront - Stunning Views and Panoramic Sunsets
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, apart-hotels, 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 €194 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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Shelter Island Heights is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.