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Shelter Island Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Shelter Island

Our top choices for Shelter Island holiday rentals

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Exterior

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Waterfront House With Dock And Private Beach
Beach nearby, sun-loungers, beach towels

Waterfront House With Dock And Private Beach

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay in Shleter island and are definitely planning to be back. The house is beautiful, very well equipped, comfortable and welcoming. The hosts were helpful and the location is amazing."
Waterfront House With Dock And Private Beach
Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1240)
"I had the best time and highly recommend this hotel!"
The price is HK$2,321
HK$2,804 total
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (406)
"great place to stay"
The price is HK$1,550
HK$1,856 total
includes taxes & fees
4 Sept - 5 Sept
Montauk Oceanside Suites
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (273)
"The front desk was great !!"
The price is HK$2,628
HK$3,428 total
includes taxes & fees
10 Sept - 11 Sept
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (238)
"Had a great time. Will be back"
The price is HK$2,591
HK$3,300 total
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (291)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is HK$1,305
HK$1,661 total
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

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
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is HK$1,599
HK$2,082 total
includes taxes & fees
3 Sept - 4 Sept
Driftwood Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is HK$2,490
HK$4,630 total
includes taxes & fees
27 Aug - 28 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (70)
"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
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is HK$1,757
HK$2,284 total
includes taxes & fees
4 Sept - 5 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Offshore Residences
Living area

Offshore Residences

4.0 star property
The price is HK$7,088
HK$8,991 total
includes taxes & fees
4 Sept - 5 Sept
Offshore Residences
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

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

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

10.0 out of 10, Exceptional, (93)
"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
On the beach

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 HK$604
HK$1,538 total
includes taxes & fees
2 Sept - 3 Sept
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is HK$1,954
HK$3,137 total
includes taxes & fees
25 Aug - 26 Aug
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Stunning Hampton Holiday Family Fantasy for your Team
TV, fireplace, video library, stereo

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (69)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
Stunning Hampton Holiday Family Fantasy for your Team
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Amazing property! Had all the things we needed "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"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 HK$1,398
HK$2,059 total
includes taxes & fees
2 Sept - 3 Sept
Shoreline Oasis
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 Hotel Reviews

Greenporter Hotel

Greenporter Hotel

10/10 Excellent
"Nice room great pool, but the employees were above and beyond friendly, welcoming, and excellent"
russell 3-night trip
Posted 2 days ago
Greenporter Hotel

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Shelter Island has to offer?

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres: This highly rated holiday home rental in Shelter Island is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

How many holiday rentals are there in Shelter Island?

Choose from 84 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Wades Beach and Gardiner's Bay Country Club are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.