Photo by tom owens

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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 140 Apartments in Shelter Island with updated reviews, rates, and availability.

Newly Renovated Montauk Condo with Ocean Views!
Fridge, microwave, oven, stovetop

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (78)
"Super clean, beautiful water views and great location. Would definitely recommend and would stay again."
Newly Renovated Montauk Condo with Ocean Views!
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior

MONTAUK MANOR-DELUXE STUDIO APARTMENT

10.0 out of 10, Exceptional, (66)
"Beautiful home and convenient to everything in Montauk."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Hamptons apartment getaway
Interior

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 932 total
includes taxes & fees
18 Apr - 19 Apr
Hamptons apartment getaway
Charming Greenport Gem 1, 1 Mile to Ferry!
Exterior

Charming Greenport Gem 1, 1 Mile to Ferry!

10.0 out of 10, Exceptional, (16)
"Wonderful place for a girls weekend. Host communicated all details and was super accommodating. "
Charming Greenport Gem 1, 1 Mile to Ferry!
Bright Apartment - 1/2 Mi to Greenport Harbor!
Fridge, microwave, stovetop, dishwasher

Bright Apartment - 1/2 Mi to Greenport Harbor!

10.0 out of 10, Exceptional, (76)
"Great stay in Greenport. The hosts, accommodations are location are wonderful. Look forward to another visit."
Bright Apartment - 1/2 Mi to Greenport Harbor!
Harbor Heights
Property grounds

Harbor Heights

9.8 out of 10, Exceptional, (6)
"perfect for visit to town and liked everything about our stay. "
Harbor Heights
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!
Interior

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, 1 bed/1.5 bath apt close to local beaches
Exterior

Private, 1 bed/1.5 bath apt close to local beaches

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay very much. Everything is as described. Vacation was perfect - we will def be back!"
Private, 1 bed/1.5 bath apt close to local beaches
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
Property grounds

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

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

10.0 out of 10, Exceptional, (5)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
The price is AED 621
AED 1,568 total
includes taxes & fees
21 Apr - 22 Apr
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Sag Harbor Suite by the Beach
1 bedroom, WiFi, bed sheets

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
The Mast at Soundview · Beach+Ocean+Sunrise
1 bedroom, desk, iron/ironing board, travel crib

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is AED 380
AED 833 total
includes taxes & fees
18 Apr - 19 Apr
The Mast at Soundview · Beach+Ocean+Sunrise
The Stern at Soundview · Beach+Ocean+Sunrise
1 bedroom, desk, iron/ironing board, free WiFi

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is AED 282
AED 713 total
includes taxes & fees
22 Apr - 23 Apr
The Stern at Soundview · Beach+Ocean+Sunrise
Inviting Beachfront Apartment in Hawk's Nest Beach
Fridge, microwave, stovetop, coffee/tea maker

Inviting Beachfront Apartment in Hawk's Nest Beach

3.0 star property
9.6 out of 10, Exceptional, (7)
"There was a complete misunderstanding about the houses. The listing doesn’t say upstairs or downstairs so we were in the wrong part of the house and the second building wasn’t one of the places to stay in so someone had to leave for no reason for the miscommunication cause we had the wrong part of the house. There needs to be more in the listing stating upstairs and down stairs. We got the place for 8 and the bedrooms couldn’t sleep 8 without guys doubling up in beds. It wasn’t intentional to be...
Inviting Beachfront Apartment in Hawk's Nest Beach
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Terrace/patio

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

10.0 out of 10, Exceptional, (147)
"Maritza and John were such lovely hosts - they helped make sure we were comfortable, lent us beach chairs and an umbrella, had a beautiful and spacious VRBO. Would definitely return again next year!!"
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Coastal Waterford Getaway, Steps to the Water!
Fridge, microwave, stovetop, dishwasher

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!
Charming Montauk Getaway centrally located
Fridge, microwave, oven, stovetop

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
MATTITUCK, #1 Winery and Beach Town !
Exterior

MATTITUCK, #1 Winery and Beach Town !

10.0 out of 10, Exceptional, (104)
"Excellent location for exploring the North Fork. Short drives to all the best places and access to 2 private beaches. Manny and Amal are very friendly, hospitable and helpful."
MATTITUCK, #1 Winery and Beach Town !
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
A heated pool

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

The price is AED 621
AED 1,568 total
includes taxes & fees
21 Apr - 22 Apr
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
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.
Don't see what you're looking for?
See all available properties in Shelter Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Shelter Island

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is AED 2,938
AED 5,267 total
includes taxes & fees
30 Apr - 1 May
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1157)
"Beautiful hotel."
The price is AED 545
AED 695 total
includes taxes & fees
1 May - 2 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (369)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water. "
The price is AED 500
AED 611 total
includes taxes & fees
20 Apr - 21 Apr
Montauk Oceanside Suites
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 90 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 top 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 19.8 mi/31.9 km away in Montauk. Free WiFi, private balconies, and Smart TVs are included. Access to an outdoor pool is available on site. Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!: It’s situated in Hampton Bays, 15.6 mi/25 km away. Includes free WiFi and Smart TVs. 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 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.