Search Apartments in Shelter Island

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Compare 105 Apartments in Shelter Island with updated reviews, rates, and availability.

Charming 2 Bedroom Guest Apartment in Essex, CT
10.0 out of 10, Exceptional, (20)
"The host had so many special touches to make this place a wonderful spot to stay. She had little snacks in the kitchen, with coffee and tea in the cupboard. There was half-and-half and the refrigerator, which we really appreciated. The towels in the bathroom were folded like you were in a special hotel. There was also lovely soap, shampoo and conditioner. Due to the cold temperature in the teens, she actually purchased some space heaters to make sure we were warm. Although there was a second...
Charming 2 Bedroom Guest Apartment in Essex, CT
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (64)
"Loved our stay! Perfect location and the place was very clean."
Newly Renovated Montauk Condo with Ocean Views!
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
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Charming Greenport Gem 1, 1 Mile to Ferry!
10.0 out of 10, Exceptional, (8)
"My family and I visited for 3 nights in late April, and this was the perfect place for us! Conveniently located in walking distance to downtown Greenport, with ample street parking, and the unit was modern, clean and spacious. The home itself is beautiful and with a lovely, well-cared-for garden. Definitely recommend!"
Charming Greenport Gem 1, 1 Mile to Ferry!
Coastal Waterford Getaway, Steps to the Water!
10.0 out of 10, Exceptional, (7)
"The location is absolutely beautiful. The apartment was clean and looked exactly like the pictures. The host was helpful and was able to communicate with me as needed. We would stay there again in a heartbeat!"
Coastal Waterford Getaway, Steps to the Water!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Tucked into the quiet woods of Sag Harbor.
Tucked into the quiet woods of Sag Harbor.
Downtown Essex Apartment - Steps to River!
10.0 out of 10, Exceptional, (14)
"We loved our stay! Apartment was perfect. Upstairs views to the harbor were lovely to wake up to. Easy, quick walk to town and restaurant. We will be sure to go back and stay there again."
Downtown Essex Apartment - Steps to River!
Homeyfeels: Nearshore 1BR with loft + Beach Access
Homeyfeels: Nearshore 1BR with loft + Beach Access
Newly Renovated Luxe 1BR+Bunkbed & Private Deck
Newly Renovated Luxe 1BR+Bunkbed & Private Deck
Water &Sunset views POOL mint studio Balcony SLEEP 5 walk2 beach harbor dock
Water &Sunset views POOL mint studio Balcony SLEEP 5 walk2 beach harbor dock
Charming Montauk Getaway centrally located
9.6 out of 10, Exceptional, (40)
"We enjoyed our stay at Mary’s little cottage that is well situated to get to everything in town. The happy surprise is that it is surrounded by flowers and tomato plants. The place had everything we needed. It is small but perfect for two. We’d love to come back."
Charming Montauk Getaway centrally located
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
Sexy CLEAN hotel style room walk to town & beach pool access
The price is AED 2,567
AED 3,350 total
includes taxes & fees
6 Jun - 7 Jun
Sexy CLEAN hotel style room walk to town & beach pool access
MATTITUCK ! The North Forks #1 Winery & Beach Town !
10.0 out of 10, Exceptional, (99)
"We enjoyed Manny and Amal’s place. It was a short walk from the beach. Beautiful garden and very welcoming hosts. It is a basement apartment which kept it cool on hot days. The kitchen had more of a toaster oven than an oven but otherwise was usable with some creativity. The grill was great. Having only one key was tricky but we worked it out. A keypad entry would be a great upgrade. We were welcomed with homemade cookies and would definitely stay again."
MATTITUCK ! The North Forks #1 Winery & Beach Town !
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
9.8 out of 10, Exceptional, (56)
"We had a good time. Great location."
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Industrial Inspired Interior 1BR+Loft & Deck view
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this property! Very clean, just steps to the beach and close to everything we love in the Hamptons!"
Industrial Inspired Interior 1BR+Loft & Deck view
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See all available properties in Shelter Island
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 property types in Shelter Island

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is AED 1,098
AED 1,325 total
includes taxes & fees
6 Jun - 7 Jun
Montauk Manor
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 AED 887
AED 1,092 total
includes taxes & fees
9 Jun - 10 Jun
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (222)
"Very nice location and nice condo"
The price is AED 914
AED 1,242 total
includes taxes & fees
13 Jun - 14 Jun
The Surf Club
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

What's it like to stay at an apartment in Shelter Island?
You’ll find plenty of places to stay in Shelter Island with 100 accommodations. Though there aren’t many apartments, we can help you search for accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages.
Why should you consider apartments instead of traditional hotels?
Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What will the weather be like when I travel to Shelter Island?
Though weather is just one factor, it can really affect your travel plans, especially when you are planning a longer stay in Shelter Island. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.
What should I see 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. While here, Shell Beach and Gardiner’s Bay Country Club are other places worth a visit.
What's the best way to get to and around Shelter Island?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. Otherwise, you can search for flights to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.

Recent reviews of Shelter Island hotels
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