Search Apartments in Shelter Island

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 91 Apartments in Shelter Island with updated reviews, rates, and availability.

Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (63)
"Loved our stay! Perfect location and the place was very clean."
Newly Renovated Montauk Condo with Ocean Views!
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
Beautiful 2bedroom w Pool close to the beach and Southampton Village
9.6 out of 10, Exceptional, (4)
"We had a wonderful stay at this property. The apartment was spacious and very clean. The outdoor area was perfect, the kids enjoyed the pool and swing/slide set. Would definitely recommend!"
Beautiful 2bedroom w Pool close to the beach and Southampton Village
Save an average of 15% on thousands of hotels when you're signed in
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
MATTITUCK ! The North Forks #1 Winery & Beach Town !
10.0 out of 10, Exceptional, (98)
"Manny is a great guide for your visit. A very quiet and private place with a beautiful patio garden."
MATTITUCK ! The North Forks #1 Winery & Beach Town !
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!
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!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
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!
Convenient and cute in Downtown Old Saybrook
9.6 out of 10, Exceptional, (42)
"I had some business in CT and decided to take a few days of rest and relaxation. I packed my sewing machine and a few books and headed north! This property was perfect. I felt safe and comfortable. I had everything I needed for a quiet weekend."
Convenient and cute in Downtown Old Saybrook
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
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 SAR 2,622
SAR 3,421 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Sexy CLEAN hotel style room walk to town & beach pool access
3 bedroom apartment near Beaches and Outlets Mall
10.0 out of 10, Exceptional, (1)
"They did a great job for one of their 1st times around! Very helpful and communicative."
3 bedroom apartment near Beaches and Outlets Mall
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!
Tucked into the quiet woods of Sag Harbor.
Tucked into the quiet woods of Sag Harbor.
Don't see what you're looking for?
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 SAR 1,121
SAR 1,353 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is SAR 906
SAR 1,116 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"Very nice location and nice condo"
The price is SAR 882
SAR 1,210 total
includes taxes & fees
17 Jum. II - 18 Jum. II
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
Expedia verified reviews