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Holiday Rentals in Shelter Island Heights

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Holiday Rentals in Shelter Island Heights

Montauk Manor
Front of property – evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1062)
"Loved the old school character "
The price is €172
includes taxes & fees
18 Nov - 19 Nov
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (258)
"Very private"
The price is €158
includes taxes & fees
6 Nov - 7 Nov
Windward Shores Ocean Resort
Montauk Oceanside Suites
Apartment | Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (336)
"It was very clean and affordable price"
The price is €130
includes taxes & fees
6 Nov - 7 Nov
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (205)
"Beautiful accommodations, friendly staff Excellent communication and very clean "
Cliffside Resort Condominiums
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (212)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (249)
"The pictures of the property showed the bed in the bedroom facing the window with direct ocean views I was dis appointed to find out the bed was moved and no longer faced the ocean view."
The price is €286
includes taxes & fees
6 Nov - 7 Nov
The Surf Club
Montauk Mansion INDOOR + OUTDOOR POOLS
Interior
Montauk Mansion INDOOR + OUTDOOR POOLS
9.6 out of 10, Exceptional, (84)
"The Montauk Manor deserves its landmark designation but it is certainly updated and thoughtfully remodelled. The space is very well laid out and there are lovely vistas from every vantage point. My biggest complaint is the noise. Not necessarily the noise of other guests, but an unexplainable mechanical noise. It was a nuisance mostly just in the quiet of the night and the only détraction to an otherwise delightful stay. "
Montauk Mansion INDOOR + OUTDOOR POOLS
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
10.0 out of 10, Exceptional, (18)
"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
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (29)
"Great home very close to a great vineyard. "
Beautiful Family Home Nestled In The Heart Of Sagaponack
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
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, (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
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (31)
"A great corner condo in the Montauk Manor. Had a wonderful weekend. The condo was clean, and a great size for 3 adults. Got to use all the facilities at the manor. Indoor pool beautiful, sauna. Great restaurant and free shuttle bus to take you to town. Just a great weekend. "
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (65)
"The place was clean and cozy. The owners could not have been nicer or more accomodating! Thanks for a great stay!"
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Newly Renovated Montauk Condo with Ocean Views!
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.8 out of 10, Exceptional, (71)
"My family stayed here for 2 nights (husband, myself and my 2 kids - age 8 and age 11). The condo was super clean and check-in was really easy. Location was amazing - right across the street from the beach and we were also able to walk into town (about a 25 min walk to town). Highly recommend this place and would defintely stay here again. "
Newly Renovated Montauk Condo with Ocean Views!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (81)
"We loved having a short getaway here. It was a beautiful location with an amazing view. The condo is indeed newly renovated and gorgeous! I wish we came during a warmer time so we can enjoy more of the on water restaurants. Nonetheless, this was a great stay and was close to everything we needed or wanted to enjoy; will definitely be staying again!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool
Gorgeous private Hamptons house with pool and volleyball court
8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (64)
"We had an incredible time at this house!!! It literally felt like we were staying at a luxury resort and had everything we could have possibly needed for our getaway. Our group included young kids and adults all of whom had an amazing stay. The tennis and basketball court was in great condition and provided endless fun activities. The pool was a great size and the heater worked well when it was needed. There is a ton of space to play sports and games as well as a fire pit which was a great way...
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!
Beach towels
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!
10.0 out of 10, Exceptional, (2)
"Lovely to be away in a spot just hidden enough to be accessible from the main road but not close to it. Near to the beach but not on top of it. Perfect! Quiet, woody, peaceful, restful and pet friendly. A hidden gem. The only thing I regret is not having time to stay longer."
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun-loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"Adorable beach cottage, great for a mother and adult daughter weekend. Location was perfect, beach just around the corner. Great halfway between NY and RI. Looking forward to booking again next Fall. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (33)
"We had a great holiday weekend at this clean, comfortable and spacious home. The property was exactly like the photos with plenty of comfy accommodations for our large group. Lots of thoughtful touches for guests and great local recommendations helped to make our stay extra memorable. The little ones in our family didn’t want to leave. Thank you!!"
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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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Other types of properties in Shelter Island Heights you may be interested in

Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (1001)
"Checkin did not go well, but the staff made it better"
The price is €82
includes taxes & fees
1 Dec - 2 Dec
Quality Inn Old Saybrook - Westbrook
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (482)
"Staff was very helpful and welcoming. Views are absolutely amazing and made our one night stay that much more memorable. "
The price is €185
includes taxes & fees
1 Dec - 2 Dec
Sound View Greenport
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (601)
"The property is lovely and the resort fee includes access to the bathhouse. The perfect getaway to reset. "
The price is €458
includes taxes & fees
24 Nov - 25 Nov
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.

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 Family Home Nestled In The Heart Of Sagaponack: This holiday home rental outside of Shelter Island Heights offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable 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 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 37 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.