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Shelter Island Heights Holiday Rentals

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Shelter Island Heights

Front of property – evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1261)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
The price is NZ$314
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.2 out of 10, Wonderful, (5)
"Very clean, great amenities! "
United States
Hayley
The price is NZ$393
includes taxes & fees
16 Nov - 17 Nov
North Fork Cottages & RV Resort
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is NZ$343
includes taxes & fees
18 Nov - 19 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
Fridge, microwave, oven, stovetop
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, (10)
"Open concept home beautiful with private yard space. It was perfect for our stay"
United States
Berlyne S.
The price is NZ$637
includes taxes & fees
8 Dec - 9 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Outdoor pool, a heated pool
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)
"Our family / extended family was in town for over a week for the Hampton Classic horse show. We all enjoyed or stay at this wonderful home: beautiful newly renovated open space, outstanding kitchens (indoors and outdoors), numerous areas to have separate down time, excellent in suite bedroom / bathrooms including three bedrooms suites with king beds, fabulous backyard with a private pool, and exceptionally clean with all amenities needed. The owners were also incredible; extremely responsive,...
United States
Kristin C.
The price is NZ$9,680
includes taxes & fees
17 Nov - 18 Nov
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

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

Old Lyme
10.0 out of 10, Exceptional, (3)
"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$711
includes taxes & fees
16 Nov - 17 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV
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$799
includes taxes & fees
17 Nov - 18 Nov
Seabreeze #3: Cozy Cottage by the beach
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Lakefront Boho Tiny House

East Lyme
10.0 out of 10, Exceptional, (3)
"My husband has always wanted to try a tiny house. This place exceeded our expectations. Lovely house. Lovely lake. He was in heaven fishing and kayaking "
United States
Asha A.
The price is NZ$399
includes taxes & fees
16 Nov - 17 Nov
Lakefront Boho Tiny House
Exterior
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
18 Nov - 19 Nov
Cozy Lakefront Tiny House
Front of property
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NZ$4,267
includes taxes & fees
23 Nov - 24 Nov
Canoe Place Waterfront Residences
Beach
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$836
includes taxes & fees
17 Nov - 18 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
Outdoor dining
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, (12)
"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.
The price is NZ$549
includes taxes & fees
17 Nov - 18 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is NZ$469
includes taxes & fees
30 Nov - 1 Dec
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is NZ$323
includes taxes & fees
23 Nov - 24 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.

Sag Harbor
The price is NZ$11,361
includes taxes & fees
18 Nov - 19 Nov
Spacious 5-bedroom house with water views and 2 houses from the bay.
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round

East Hampton
9.4 out of 10, Exceptional, (3)
"Just hubby & I. Great fireplace and deck with very clean bubbly hot tub. Comfy king-sized bed. Kitchen was clean & functional with basics. Backyard appeared larger in pictures. Rental could use extra couch in living room to comfortably fit eight ppl. The living room couch is just for sitting, appears larger in pictures. Couch is"
United States
STEPHANIE C.
The price is NZ$1,556
includes taxes & fees
17 Nov - 18 Nov
Blackberry: Private home with jacuzzi year-round
Terrace/patio
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)
"What a great place for a family gathering! The backyard is to die for and the host was very helpful throughout the stay. We’ll be back!!"
United States
Lisa w.
The price is NZ$2,246
includes taxes & fees
23 Nov - 24 Nov
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Fridge, microwave, stovetop, dishwasher
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$973
includes taxes & fees
18 Nov - 19 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays
10.0 out of 10, Exceptional, (12)
"This is a simple house with a great view right on the water. The beds and bedding were comfortable. Despite being on the water, it has a nice yard and little beach area. "
United States
Coleman H.
The price is NZ$2,361
includes taxes & fees
17 Nov - 18 Nov
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
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.
The price is NZ$341
includes taxes & fees
14 Nov - 15 Nov
The Anchor at Soundview · Beach+Ocean+Sunrise
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

Sea Crest Resort

Sea Crest Resort

10/10 Excellent
"Location. Staff. Space. "
claudia 2-night trip
Posted 4 days ago
Sea Crest Resort

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$314 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?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Shelter Island Heights is located near the beach, and has an outdoor pool, a fireplace and a BBQ 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 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 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.