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

MONTAUK MANOR-DELUXE STUDIO APARTMENT
Front Entrance

MONTAUK MANOR-DELUXE STUDIO APARTMENT

10.0 out of 10, Exceptional, (65)
"The place was clean and cozy. The owners could not have been nicer or more accomodating! Thanks for a great stay!"
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Greenport Vacation Rental | 1BR | 1BA | 400 Sq Ft | Stairs Required

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

9.8 out of 10, Exceptional, (60)
"Very nice spot for a couple to stay. Fully equipped and thoughtfully laid out. Comfortable bed. Updated in all ways. Exceptionally clean and well stocked. Very convenient to downtown and extremely walkable."
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Newly Renovated Montauk Condo with Ocean Views!
Property grounds

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (71)
"My family stayed here for 2 nights (husband, myself and my 2 kids - age 8 and age 11). The condo was super clean and check-in was really easy. Location was amazing - right across the street from the beach and we were also able to walk into town (about a 25 min walk to town). Highly recommend this place and would defintely stay here again. "
Newly Renovated Montauk Condo with Ocean Views!
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.
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!
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
Homeyfeels: Nearshore 1BR with loft + Beach Access
Living area

Homeyfeels: Nearshore 1BR with loft + Beach Access

Homeyfeels: Nearshore 1BR with loft + Beach Access
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
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
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!
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 !
Unit 1022 - Ocean Colony Beach and Tennis Club
Living area

Unit 1022 - Ocean Colony Beach and Tennis Club

6.0 out of 10, (1)
Unit 1022 - Ocean Colony Beach and Tennis Club
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, (15)
"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!
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
Living area

TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!

2.0 out of 10, (1)
"The accommodation was extremely old like 1970 and hadn’t been renovated since then. Old discusting furniture. They said queen bed only full. The steps and hallway outside was littered with crumbs and crackers. Bags of garbage were outside. The beach was best part from what I could.l see The pool was small and very old. The steps down to the beachwere creepy and many. There are much better motels for less money in the area. Not a place for seniors or anyone with handicaps. "
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
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!
Tucked into the quiet woods of Sag Harbor.
Outdoor dining

Tucked into the quiet woods of Sag Harbor.

Tucked into the quiet woods of Sag Harbor.
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
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
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
Long Island Sound Studio
View from the front step

Long Island Sound Studio

10.0 out of 10, Exceptional, (9)
"The studio cottage was charming, quiet and a stone’s throw to the calm waters of the Sound showcasing remarkable views, including the Old Saybrook Light and Finwick Light too. "
Long Island Sound Studio
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, (1069)
"Absolutely everything my girlfriend and I could have asked for. Will be happy to return one day!"
The price is AED 537
AED 685 total
includes taxes & fees
25 Nov - 26 Nov
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (338)
"All very good!"
The price is AED 423
AED 520 total
includes taxes & fees
26 Nov - 27 Nov
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is AED 464
AED 609 total
includes taxes & fees
3 Dec - 4 Dec
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 95 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's a favorite apartment for my stay in Shelter Island?
Below are some of the more popular apartments in the area: MONTAUK MANOR-DELUXE STUDIO APARTMENT: Located in Montauk, 20.2 mi/32.5 km from the heart of Shelter Island. Includes free WiFi, fireplaces, and sofa beds. A fitness center and an outdoor pool are on site. Newly Renovated Montauk Condo with Ocean Views!: Located in Montauk, 19.8 mi/31.9 km away. Includes free WiFi, private balconies, and Smart TVs. Access to an outdoor pool is available on site. Hamptons apartment getaway: 20.1 mi/32.4 km away in East Quogue. Free WiFi and Smart TVs are included.
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, Shelter Island Historical Society and Mashomack Preserve 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.