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Shelter Island Heights Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Shelter Island Heights

Front of property – evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1261)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
The price is HK$1,077
HK$1,383 total
includes taxes & fees
4 Dec - 5 Dec
Montauk Manor
Private kitchen
Montauk Oceanside Suites

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
Beach nearby
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (247)
"Location good. Room could use some renos."
United States
Laura
Cliffside Resort Condominiums
Private kitchen
Driftwood Resort

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (235)
"Great place for families and to enjoy the beauty of Montauk without being in Montauk town. Beautiful beach next to a state park so feels secluded and not crowded. Highly recommend!!!"
United States
Angel
Driftwood Resort
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is HK$804
HK$1,710 total
includes taxes & fees
12 Nov - 13 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
Living area
Offshore Residences

Offshore Residences

4.5 star property
Downtown Montauk
The price is HK$3,724
HK$5,142 total
includes taxes & fees
12 Nov - 13 Nov
Offshore Residences
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

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

Montauk
9.4 out of 10, Exceptional, (40)
"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. "
United States
Madison
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Exterior
Shoreline Oasis

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is HK$1,392
HK$2,026 total
includes taxes & fees
12 Nov - 13 Nov
Shoreline Oasis
On the beach, white sand
The Surf Club

The Surf Club

3.5 star property
Montauk
8.6 out of 10, Excellent, (280)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The Surf Club
Smart TV, fireplace, stereo
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

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

East Hampton
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"
United States
Edward
The price is HK$1,679
HK$2,149 total
includes taxes & fees
12 Nov - 13 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
The price is HK$5,558
HK$9,191 total
includes taxes & fees
27 Nov - 28 Nov
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
9.8 out of 10, Exceptional, (34)
"This old colonial home was very charming. We enjoyed our stay. The only thing to be aware of is there is only air conditioning in 4 of the bedrooms and it was quite hot while we were there. The location is great, and it's a short walk in to town."
United States
LauraLee E.
Large Charming Historic House close to Beaches
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is HK$591
HK$1,503 total
includes taxes & fees
12 Nov - 13 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
Waterford
10.0 out of 10, Exceptional, (12)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is HK$1,166
HK$2,515 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk
10.0 out of 10, Exceptional, (61)
"Amazing stay…. Great host, excellent location and very clean!"
Australia
Amy W.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Interior
MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK
9.8 out of 10, Exceptional, (76)
"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! "
United States
Katie M.
MONTAUK MANOR-DELUXE STUDIO APARTMENT
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

Sea Crest Resort

Sea Crest Resort

10/10 Excellent
"Location. Staff. Space. "
claudia 2-night trip
Posted 2 days ago
Sea Crest Resort

Find out more about Shelter Island Heights

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:

  • View our selection of featured holiday rentals in Shelter Island Heights
  • Use the map to find apartments and other holiday homes in the Shelter Island Heights neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island Heights while they last

Look no further and take a look at our great range of rental properties in Shelter Island Heights!

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?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Shelter Island Heights is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 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 33 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.