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Shelter Island Heights Vacation Rentals

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Vacation Rentals in Shelter Island Heights

Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1024)
"Best affordable hotel in Montauk"
The price is ￥61,600
￥73,348 total
includes taxes & fees
Jun 20 - Jun 21
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (238)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is ￥37,662
￥46,371 total
includes taxes & fees
Jun 9 - Jun 10
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (222)
"Very nice location and nice condo"
The price is ￥40,166
￥54,310 total
includes taxes & fees
Jun 24 - Jun 25
The Surf Club
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Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (302)
"This is our second time staying at Montauk Oceanside Suites and we enjoyed both times. It is very close to the beach and a short walk to dining options. We only used of car once(to dine on the bay side) over three days. We would defiantly stay there again."
The price is ￥33,287
￥39,547 total
includes taxes & fees
Jun 12 - Jun 13
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (188)
"Well maintained upscale resort. "
The price is ￥30,864
￥38,611 total
includes taxes & fees
Jun 9 - Jun 10
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is ￥43,762
￥56,718 total
includes taxes & fees
Jun 27 - Jun 28
Cliffside Resort Condominiums
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (12)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Newly Renovated Montauk Condo with Ocean Views!
Beach nearby, sun loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (64)
"This property was beautiful and Freddy was great. It had everything we needed and will definitely be staying there again. "
Newly Renovated Montauk Condo with Ocean Views!
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (50)
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
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, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
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, (28)
"Rainy but good weekend"
The price is ￥50,671
￥93,395 total
includes taxes & fees
Jun 13 - Jun 14
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (55)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
North Fork Escape Near Wineries, Beaches And Hamptons
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
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, (91)
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
70 Year old cottage on 2.8 acres, stunning views and sunsets
Interior
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Montauk Mansion With Outdoor Pool
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
Beach nearby
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
9.8 out of 10, Exceptional, (12)
"Loved the location to the beach and neighborhood. Great for a weekend getaway."
4 bedroom 2.5 bathroom A/C Decks Pvt Beach /HotTub/FirePit
Don't see what you're looking for?
See all available properties in Shelter Island Heights
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.

Other types of properties in Shelter Island Heights you may be interested in

The Rams Head Inn
Exterior
The Rams Head Inn
4.0 star property
9.2 out of 10, Wonderful, (7)
"It's traditional, quaint, serene, and the air is fresh"
The price is ￥54,091
￥61,731 total
includes taxes & fees
Jun 17 - Jun 18
The Rams Head Inn
Pier Blue Inn Old Saybrook - Essex
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (789)
"Most of these reviews give less than 5 stars because it’s outdated, which it is, but other than that I love my stay. I had no issues. Front desk staff were super friendly. Coffee machine in the room which was nice. Great area and location too, a lot of restaurants in walking distance. They are in the middle of renovations so keep that in mind but I’m excited to come back when it’s completed!! "
The price is ￥12,235
￥14,070 total
includes taxes & fees
Jun 17 - Jun 18
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook
Indoor pool, sun loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (967)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great. "
The price is ￥15,665
￥18,014 total
includes taxes & fees
Jun 17 - Jun 18
Quality Inn Old Saybrook - Westbrook
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.

Search for holiday rentals in Shelter Island Heights on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island Heights using one of the methods below:

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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?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: Visitors like this Shelter Island Heights vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, 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 30 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.

Recent reviews of Shelter Island Heights properties
Expedia verified reviews

Sleep Inn & Suites Niantic

Sleep Inn & Suites Niantic

5/5 Excellent
"Clean, had all the necessary amenities, enjoyed the waffle maker at breakfast."
A verified traveler stayed at Sleep Inn & Suites Niantic
Posted 19 hours ago
Sleep Inn & Suites Niantic