Photo by Erisa Dilo

Shelter Island Heights Holiday Rentals

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Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

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, (1111)
"Amazing place! "
The price is AU$266
includes taxes & fees
18 Feb - 19 Feb
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (361)
"I rented a room with a kitchen. And all it had was a fridge and microwave… otherwise I love it there"
The price is AU$217
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
18 Feb - 19 Feb
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (251)
"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 Surf Club
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, (98)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
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, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team
10 Bedroom Hampton House with a regulation size Pickleball
Pool

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
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, (75)
"Montauk has been our Happy Place for many years. We feel fortunate to have discovered this charming condo. Comfortable-feels like home. Immaculate. Consideration went into the details. Luxurious towels. Fantastic location near beach. And owner is a pleasure, right on top of communication. This place made our visit even Happier. Highly recommend. Thank You! Lynn"
Newly Renovated Montauk Condo with Ocean Views!
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!
Montauk Mansion INDOOR + OUTDOOR POOLS
Interior

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (88)
"Well kept unit. Easy access. Very quiet. Pool and spa area beautiful "
Montauk Mansion INDOOR + OUTDOOR POOLS
adorable ranch in beach community
Beach nearby

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (214)
"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
Summer 2025 Now Available! Wolffer Vineyard Close!
Outdoor pool, a heated pool

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship
A heated pool

Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship
Historical New England coastal holiday home-2 min. from Ocean Beach
Interior

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (33)
"The host was incredibly kind and accommodating. We particularly enjoyed the beach pass, as we drove ~3 min to the beautiful water in the morning. The amenities were absolutely gorgeous and beyond functional. Plenty of bathrooms, showers, sinks, sitting areas, etc. for our party. We had a wonderful stay!"
Historical New England coastal holiday home-2 min. from Ocean Beach
Oceanfront Beach House lay in bed and hear the waves, boats , birds
On the beach, sun-loungers, beach towels

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
Sun-loungers, beach towels

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (5)
"Our stay at Carters home was nothing short of perfect! Every day we walked to the beach, explored the charming town, grabbed coffee at Hampton Coffee, and enjoyed incredible restaurants nearby. Coming back to such a beautiful and comfortable house felt like a dream. We loved starting our mornings on the patio and cooling off in the pool and eating outside on the big table surrounded by lush flowers—absolute bliss! Highly recommend!""
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10
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
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
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
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

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1111)
"Amazing place! "
The price is AU$266
includes taxes & fees
18 Feb - 19 Feb
Montauk Manor
Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1004)
"Fabulous property! Fantastic spa! Staff is friendly. Views are stunning. "
The price is AU$335
includes taxes & fees
3 Mar - 4 Mar
Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex
Property grounds

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.6 out of 10, Good, (917)
"Quiet, was able to sleep during the day as I work overnights. Staff was friendly and accommodating "
The price is AU$125
includes taxes & fees
18 Feb - 19 Feb
Pier Blue Inn Old Saybrook - Essex
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?

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10: 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 3 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 balcony, 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 40 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.