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Shelter Island Heights Vacation Rentals

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Vacation Rentals in Shelter Island Heights

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1021)
"Best affordable hotel in Montauk"
The price is $168
$211 total
includes taxes & fees
May 23 - May 24
Montauk Manor
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (296)
"We enjoyed our stay!"
The price is $164
$197 total
includes taxes & fees
Jun 5 - Jun 6
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is $174
$253 total
includes taxes & fees
May 30 - May 31
The Surf Club
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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 $154
$197 total
includes taxes & fees
May 22 - May 23
Windward Shores Ocean Resort
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 $186
$256 total
includes taxes & fees
May 27 - May 28
Cliffside Resort Condominiums
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (185)
"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 $162
$207 total
includes taxes & fees
Jun 5 - Jun 6
Driftwood Resort
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
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
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (72)
"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!
Beach nearby, sun loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (62)
"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!
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
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 $325
$597 total
includes taxes & fees
Jun 13 - Jun 14
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
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!!!
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, (91)
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
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
Outdoor pool
Beautiful 3 bedroom Residence in the Hamptons
Beautiful 3 bedroom Residence in the Hamptons
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
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
Interior
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
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.

Shelter Island Heights Vacation Rental Travel Info

Number of vacation rentals
45
Popular accommodation
Shelter Island Heights private vacation homes
Known landmarks
Raphael Winery, Orient Beach State Park and Bedell Cellars
International airports
New York, NY (JFK-John F. Kennedy Intl.), Newark, NJ (EWR-Liberty Intl.) and New York, NY (LGA-LaGuardia)

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

Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (568)
"Great time beautiful property"
The price is $523
$714 total
includes taxes & fees
Jun 2 - Jun 3
Gurney's Montauk Resort & Seawater Spa
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (780)
"This is a no-frills hotel. However we had a mini fridge, microwave and coffee maker in our room. VERY spacious. Staff were friendly and at the front desk when we needed them to be there. A lady came to our door once to see if we needed fresh towels (we were there for 6 days). We will stay here on a return visit. Thanks Pier Blue staff"
The price is $83
$96 total
includes taxes & fees
May 29 - May 30
Pier Blue Inn Old Saybrook - Essex
Lobby
Motel 6 Niantic, CT - New London
2.0 star property
7.2 out of 10, Good, (1001)
"No shampoo, and the smallest soap bar I ever saw,and no tissues. Outside walkway was crumbling in many places"
The price is $65
$75 total
includes taxes & fees
May 22 - May 23
Motel 6 Niantic, CT - New London
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.

Everything you need to know about Shelter Island Heights vacation rentals

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

Shelter Island Heights vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shelter Island Heights in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to 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's the top vacation rental that Shelter Island Heights has to offer?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: Visitors like this Shelter Island Heights vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island Heights?

With 29 Expedia vacation rentals, you're sure 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 vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.

Recent reviews of Shelter Island Heights properties
Expedia verified reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

5/5 Excellent
"Great time beautiful property"
A verified traveler stayed at Gurney's Montauk Resort & Seawater Spa
Posted 16 hours ago
Gurney's Montauk Resort & Seawater Spa