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Holiday Rentals in Shelter Island Heights

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Holiday Rentals in Shelter Island Heights

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1236)
"I had the best time and highly recommend this hotel!"
The price is €307
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (405)
"great place to stay"
The price is €203
includes taxes & fees
3 Sept - 4 Sept
Montauk Oceanside Suites

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (270)
"The front desk was great !!"
The price is €375
includes taxes & fees
3 Sept - 4 Sept
The Surf Club

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great location, great views. Walls are a little thin."
The price is €361
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (290)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is €182
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.8 out of 10, Excellent, (26)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is €228
includes taxes & fees
3 Sept - 4 Sept
Driftwood Resort

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is €458
includes taxes & fees
21 Aug - 22 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (69)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (91)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is €171
includes taxes & fees
19 Aug - 20 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

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

Shoreline Oasis

9.0 out of 10, Wonderful, (6)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is €225
includes taxes & fees
26 Aug - 27 Aug
Shoreline Oasis

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is €857
includes taxes & fees
19 Aug - 20 Aug
Southampton cozy cottage by the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

9.6 out of 10, Exceptional, (37)
"we had a lovely stay in this apartment! it was very spacious and comfortable. The pull out couch was also surprisingly very comfy! Mark and Nancy were very responsive and helpful. "
The price is €571
includes taxes & fees
4 Sept - 5 Sept
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
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

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island Heights?

With 47 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.