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Shelter Island Heights Vacation Rentals

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Vacation Rentals in Shelter Island Heights

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1052)
"Great hotel loved the architecture and the grounds. "
The price is CA $385
CA $466 total
includes taxes & fees
Sep 24 - Sep 25
Montauk Manor
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (247)
"On the beach Heated pool Great facilities"
The price is CA $342
CA $464 total
includes taxes & fees
Oct 7 - Oct 8
The Surf Club
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (334)
"Close to the beach and the town of Montauk "
The price is CA $191
CA $231 total
includes taxes & fees
Oct 23 - Oct 24
Montauk Oceanside Suites
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (252)
"A unos pasos del océano , muy tranquilo el lugar , limpio, espero volver pronto . "
The price is CA $179
CA $234 total
includes taxes & fees
Oct 14 - Oct 15
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (202)
"Excellent place! Convenient for beach. Amazing pool, Cabana staff etc. lovely room - everything was perfect for our needs!"
The price is CA $235
CA $298 total
includes taxes & fees
Sep 24 - Sep 25
Driftwood Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (201)
"Beautiful condo Convienent Spacious Only issue check in 4 pm Checkout at 10 am "
The price is CA $423
CA $542 total
includes taxes & fees
Sep 24 - Sep 25
Cliffside Resort Condominiums
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
10.0 out of 10, Exceptional, (17)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Newly Renovated Montauk Condo with Ocean Views!
9.8 out of 10, Exceptional, (69)
"Beautiful condo - great location. Would stay here again."
Newly Renovated Montauk Condo with Ocean Views!
Montauk Mansion INDOOR + OUTDOOR POOLS
9.8 out of 10, Exceptional, (82)
"Everything was as described and went well."
Montauk Mansion INDOOR + OUTDOOR POOLS
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (28)
"House was lovely, great neighborhood! We enjoyed our stay"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (80)
"Rick was a gracious host; the house was clean, and the beach was nearby. We enjoyed our stay "
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (78)
"The unit was beautifully appointed and we had everything we needed. It was close enough to walk to town, yet far enough to be a peaceful, relaxing stay and the view was perfect. Our stay could not have been better. We will definitely be back!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.2 out of 10, Wonderful, (31)
"Very comfortable and functional for three adults traveling to Montauk for a wedding. Would stay again. "
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (64)
"My wife and I had a wonderful stay in Montauk ! It brought back a lot of memories for us. Robert’s apartment was just what we needed for our stay. It has all the comforts of home ! We had one small hiccup, but Robert responded immediately and all was taken care of. We would definitely be back ! Thank you for the hospitality Robert !"
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, (18)
"This is our third visit to Little Neck and we loved it once again! Perfect location and we had everything we needed for another enjoyable and memorable vacation. We also love that we can bring our dog which is so nice. Lori is a wonderful host and super responsible. Highly recommend."
Location and views! Located directly on Shinnecock Bay!
Gorgeous private Hamptons house with pool and volleyball court
8.4 out of 10, Very good, (12)
"Ok, if you are considering staying here, place is big and nice open concept. Two big refridgerators and kitchen dining room are lovely. Pool tables felt is very dirty and cues are down to wood. Outside pool is cracked and leaking so hose water needs to be constantly running making water cold. Deck has many soft spots and a couple of holes. Not like picture...no plants and outdoor furniture moldy....would not sit on love seat area. No one did. Needs a good bleaching. Great to have a washer and...
Gorgeous private Hamptons house with pool and volleyball court
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (97)
"Nothing negative to say. The owner came to greet us on our arrival, and showed us around the property. The house and grounds are family friendly with safety features for toddlers. Plenty of room for a large group. Parking for one car at the beach, and a short walk if all cannot fit in the car. The two outdoor showers are great when returning from the beach."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, (9)
"This is a beautiful, comfortable and recently renovated home in a lovely neighborhood. The yard is also very nice, it was too cold for the pool but we enjoyed the hot tub and outdoor seating areas. We had a wonderful stay!"
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (31)
"Chris was the most proactive host we've had. He reached out while we were on our way to give us additional details and checked in throughout our stay to make sure we had what we needed. The shallow section of the pool was shallow enough for our 4 year old to stand which made the time in the pool even more fun. Also the pool was off to the side of the property and fenced in which gave us more security that our boys wouldn't go in accidently. The fire pit was a great place to hang out and we had...
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Sag Harbor Suite by the Beach
8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
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Other types of properties in Shelter Island Heights you may be interested in

The Rams Head Inn
4.0 star property
7.6 out of 10, Good, (14)
"Beautiful views and lovely service "
The Rams Head Inn
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (855)
"Very helpful, real people! Many dinning options within two minutes. "
The price is CA $107
CA $123 total
includes taxes & fees
Sep 24 - Sep 25
Pier Blue Inn Old Saybrook - Essex
Montauk Yacht Club
4.0 star property
8.4 out of 10, Very good, (1007)
"beautiful room and view , stayed with my 2 year old staff was lovely "
The price is CA $324
CA $448 total
includes taxes & fees
Sep 24 - Sep 25
Montauk Yacht Club
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.

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?

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: You might want to consider this vacation rental near Shelter Island Heights, which is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, 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 36 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.