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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 116 Apartments in Shelter Island with updated reviews, rates, and availability.

Newly Renovated Montauk Condo with Ocean Views!
Cozy, open living area with lots of natural light.

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (76)
"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 MANOR-DELUXE STUDIO APARTMENT
Front Entrance

MONTAUK MANOR-DELUXE STUDIO APARTMENT

10.0 out of 10, Exceptional, (66)
"We had such an amazing time at Montauk Manor! The studio had everything we needed to cook a couple meals and to unplug and relax together! Best valentine's day weekend! Thank you Robert!"
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!
Living area

Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!

9.6 out of 10, Exceptional, (5)
"Great place great price nice people. This is an apartment in someone’s house, they were welcoming and helpful. Definitely would stay here again."
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Hydrangea Blooming Morning

Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.

10.0 out of 10, Exceptional, (147)
"Maritza and John were very friendly hosts and we even met their lovely dog Sara! Central location to Greenport. You have access to the top floor of the house where it is both homely and inviting. Would stay here again"
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Homeyfeels: Nearshore 1BR with loft + Beach Access
Living area

Homeyfeels: Nearshore 1BR with loft + Beach Access

Homeyfeels: Nearshore 1BR with loft + Beach Access
Ocean Dunes at Amagansett
Lobby

Ocean Dunes at Amagansett

2.5 star property
8.6 out of 10, Excellent, (8)
"Ocean Dunes is a perfect place where the beach meets the village."
Ocean Dunes at Amagansett
Water &Sunset views POOL mint studio Balcony SLEEP 5 walk2 beach harbor dock
Outdoor dining

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
Harbor Heights
Living area

Harbor Heights

9.4 out of 10, Exceptional, (3)
"got engaged while we stayed for a quick weekend away, and had a great time with my fiancé. good location and clean."
Harbor Heights
Sag Harbor Suite by the Beach
Beach

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Interior

A Touch of Ocean Studio, 1 BTH & Balcony Apt!

10.0 out of 10, Exceptional, (5)
"Being literally on the beach with resident access to chairs towels umbrellas and snacks is really awesome."
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
The Mast at Soundview · Beach+Ocean+Sunrise
Queen Bedroom - 50" Roku TV

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is AED 413
AED 882 total
includes taxes & fees
23 Feb - 24 Feb
The Mast at Soundview · Beach+Ocean+Sunrise
Charming Greenport Gem 1, 1 Mile to Ferry!
Greenport Vacation Rental | 2BR | 1BA | Stairs Required | 900 Sq Ft

Charming Greenport Gem 1, 1 Mile to Ferry!

10.0 out of 10, Exceptional, (16)
"Beautiful property is in a safe walkable area near restaurants and shops. Off street parking was easy to find. Lovely garden path leads you to the front door. Interior flight of curved/circular stairs takes you up one flight to door. Maybe tricky for someone with mobility issues. Bedrooms and one bath were clean, nicely decorated and well stocked with the essentials including soaps, hair dryer and tissues. Kitchen was bright. Please note there is minimal counter space but well stocked...
Charming Greenport Gem 1, 1 Mile to Ferry!
Charming Montauk Getaway centrally located
Private kitchen

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (42)
"The property was perfect for two people who want a cozy space, perfect location, and a wonderful and helpful owner. Would definitely return."
Charming Montauk Getaway centrally located
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Living area

Modern Studio Apt w/ Balcony & Pool View | 1 BTH

Modern Studio Apt w/ Balcony & Pool View | 1 BTH
MATTITUCK, #1 Winery and Beach Town !
Like having your own private beach

MATTITUCK, #1 Winery and Beach Town !

10.0 out of 10, Exceptional, (104)
"We meet Manny when we arrived at the property and he showed us around and gave us great tips on things to do and beaches to visit, his wife found out it was my wife's birthday and she made her a special dessert. It was a great time. "
MATTITUCK, #1 Winery and Beach Town !
Industrial Inspired Interior 1BR+Loft & Deck view
Living area

Industrial Inspired Interior 1BR+Loft & Deck view

10.0 out of 10, Exceptional, (2)
"There for a race and only really slept there, but the place was nice."
Industrial Inspired Interior 1BR+Loft & Deck view
Hamptons apartment getaway
Room

Hamptons apartment getaway

10.0 out of 10, Exceptional, (1)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
The price is AED 459
AED 815 total
includes taxes & fees
23 Feb - 24 Feb
Hamptons apartment getaway
Montauk’s Secret Private Spot
Beach

Montauk’s Secret Private Spot

8.0 out of 10, Very Good, (1)
"The property was in a lovely area. It was very quiet and private. Beach is walking distance and the host was very friendly and accommodating "
Montauk’s Secret Private Spot
Coastal Waterford Getaway, Steps to the Water!
Waterford Vacation Rental | 1BR | 1BA | 587 Sq Ft | Stairs Required

Coastal Waterford Getaway, Steps to the Water!

10.0 out of 10, Exceptional, (12)
"We stayed here while visiting our son. The place looks brand new, right on the water, super quiet (I don't think we heard a noise the whole weekend). Nice community/area, would definitely stay here again. Ned was super nice and gave us two great recommendations for dinner. "
Coastal Waterford Getaway, Steps to the Water!
The Stern at Soundview · Beach+Ocean+Sunrise
Queen Bedroom - 50" Roku TV

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is AED 413
AED 882 total
includes taxes & fees
23 Feb - 24 Feb
The Stern at Soundview · Beach+Ocean+Sunrise
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 property types in Shelter Island

Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1116)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is AED 481
AED 621 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AED 412
AED 507 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (273)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is AED 484
AED 632 total
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort
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 89 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 Shelter Island Historical Society 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.