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Shelter Island Heights Holiday Rentals

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Holiday Rentals in Shelter Island Heights

Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (89)
"We unfortunately had bad weather during our stay but we were cozy in this home which is spacious and conveniently located. For those with kids, there are safety gates and toys available. There’s a lot of outdoor seating and in the summer we look forward to returning to take advantage of the pool. Carter is very responsive - a terrific host!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"We had a wonderful week and enjoyed being in this beautiful manor immensely. We strolled the grounds and caught gorgeous sunsets. The shuttle into downtown Montauk (5 mins away) allowed us to untether from our car and parking worries, and to spend time at the ocean and wandering the quaint downtown. It was the perfect spot and we would go back again."
Montauk Mansion With Outdoor Pool
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (73)
"We enjoyed our stay. No complaints. Great location."
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Beach nearby, sun-loungers, beach towels
Beach House
9.8 out of 10, Exceptional, (42)
"This was such a cute place. We visited in spring where everything is just start to bloom the yard was fenced in so great for dogs, with a cute play place for kids. The neighborhood is so quiet and peaceful. We walked several of the streets and meet a few friendly neighbors. The host was fantastic checking in to make sure we had everything we needed. The house was clean, Air with lots of windows and light. We spent time playing board games and reconnect. Definitely would come the area again and...
Beach House
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (60)
"Perfect spot in Montauk, close to the beach and town. We walked to town with a 3 year old and infant in the stroller and very doable nice walk. The condo is clean and equipped with basic necessities so bring anything you might need cooking wise. Kept the baby in the bedroom and our 3 year old in the living room but we made it work. Kelly is extremely responsive and a pleasure to rent from."
Newly Renovated Montauk Condo with Ocean Views!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
The price is HK$2,535
per night
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is HK$1,311
per night
20 May - 21 May
Montauk Manor
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is HK$1,919
per night
19 May - 20 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is HK$1,199
per night
19 May - 20 May
Windward Shores Ocean Resort
Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (184)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is HK$1,268
per night
2 Jun - 3 Jun
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"Very nice location and nice condo"
The price is HK$1,747
per night
9 Jun - 10 Jun
The Surf Club
Don't see what you're looking for?
See all available properties in Shelter Island Heights
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.

Other types of properties in Shelter Island Heights you may be interested in

Exterior
The Rams Head Inn
3.0 star property
9.2 out of 10, Wonderful, (7)
"It's traditional, quaint, serene, and the air is fresh"
The price is HK$2,002
per night
28 May - 29 May
The Rams Head Inn
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1020)
"Best affordable hotel in Montauk"
The price is HK$1,311
per night
20 May - 21 May
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (565)
"Amazing beds "
The price is HK$4,107
per night
23 May - 24 May
Gurney's Montauk Resort & Seawater Spa
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.

Search for holiday rentals in Shelter Island Heights on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island Heights using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island Heights
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Look no further and take a look at our great range of rental properties in Shelter Island Heights!

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.

How many holiday rentals are there in Shelter Island Heights?

With 29 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.

Recent reviews of Shelter Island Heights properties
Expedia verified reviews

Sag Harbor Inn

Sag Harbor Inn

5/5 Excellent
"Kind and clean "
A verified traveller stayed at Sag Harbor Inn
Posted 3 days ago
Sag Harbor Inn