Shelter Island Vacation Rentals from $166: Search Short-Term Rentals

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Our top choices for Shelter Island vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Greenport

William

$266 nightly

Nov 12 - Nov 13

Total with taxes and fees

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

2. The SandPiper

Pipes Cove

Manuela C.

$213 nightly

Nov 10 - Nov 11

Total with taxes and fees

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. Aqua Vista

Pipes Cove

Kerri L.

$223 nightly

Nov 9 - Nov 10

Total with taxes and fees

A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Pipes Cove

Steven R.

$213 nightly

Nov 3 - Nov 4

Total with taxes and fees

A beach with people relaxing, a pier extending into the water, and a clear sky.

5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

$321 nightly

Nov 2 - Nov 3

Total with taxes and fees

A wooden pathway leading to a beach with scattered rocks and greenery.

6. Beach Block Hideaway

Pipes Cove

Teresa C.

$394 nightly

Nov 3 - Nov 4

Total with taxes and fees

A modern house with a deck, outdoor seating, and a fire pit.

7. North Fork Resort

Greenport

Altynai

$296 nightly

Nov 4 - Nov 5

Total with taxes and fees

An outdoor dining area with hanging lights, palm trees, and a bar.

8. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

$268 nightly

Oct 29 - Oct 30

Total with taxes and fees

A spacious hallway with high ceilings, arched columns, and chandeliers.

9. Montauk Manor

Montauk

Maria

$163 nightly

Nov 17 - Nov 18

Total with taxes and fees

10. Driftwood Resort

Montauk

Julian

$166 nightly

Oct 30 - Oct 31

Total with taxes and fees

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

11. Renovated Townhouse walk to all

Greenport

Liz H.

$510 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern dining area with a wooden table, white chairs, and a chandelier.

12. Northfork Townhouse walk to all

Greenport

Beth R.

$504 nightly

Nov 10 - Nov 11

Total with taxes and fees

13. Windward Shores Ocean Resort

Napeague

Banessa

$156 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

14. Charming Accommodations in the Hamptons

Sag Harbor

$446 nightly

Nov 2 - Nov 3

Total with taxes and fees

A modern living room with a sofa, coffee table, and dining area.

15. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

$783 nightly

Nov 10 - Nov 11

Total with taxes and fees

A dining area with a round table, six chairs, and a chandelier.

16. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

$1,380 nightly

Nov 8 - Nov 9

Total with taxes and fees

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

17. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

$985 nightly

Oct 29 - Oct 30

Total with taxes and fees

18. Montauk Oceanside Suites

Downtown Montauk

Jadana

$146 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

19. Beachfront Greenport Villa

Greenport

Kate R.

$929 nightly

Nov 11 - Nov 12

Total with taxes and fees

A stone pier leading to a beach with houses in the background.

20. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

Emily M.

$244 nightly

Oct 31 - Nov 1

Total with taxes and fees

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Top Shelter Island Hotel Reviews

Sun N Sound

10/10 Excellent

"Location, very clean, comfortable"

Zey Hotel

10/10 Excellent

"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of the hydrants was causing the dirty water. The manager promptly told us we could stay until 6:00 pm for free, so that we would be able to take clean showers. We told him that we had showered early, and that we had no problem. But his response showed how he cared for the guests."

Saybrook Point Resort & Marina

10/10 Excellent

"A wonderful getaway. It was lovely. The room was beautiful with a fireplace they came and started for us. We had a balcony over looking the marina, and river. The sunrises were amazing. Great places to walk or take a resort bike. We were there in October and it was great. I will take out of season any day. Old Saybrook is a treasure."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

Find out more about Shelter Island

Everything you need to know about Shelter Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Sag Harbor

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation home rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island?

Choose from 87 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Mashomack Preserve and Sunset Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Wades Beach are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

Shelter Island Vacation Rentals

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Check prices for these dates

Our top choices for Shelter Island vacation rentals

1. Cliffside Resort Condominiums

2. The SandPiper

3. Aqua Vista

4. Harbor Heights

5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

6. Beach Block Hideaway

7. North Fork Resort

8. American Beech in Greenport - Petite King Room 7

9. Montauk Manor

10. Driftwood Resort

11. Renovated Townhouse walk to all

12. Northfork Townhouse walk to all

13. Windward Shores Ocean Resort

14. Charming Accommodations in the Hamptons

15. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

16. Year round Jacuzzi - Blackberry East Hampton Home

17. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

18. Montauk Oceanside Suites

19. Beachfront Greenport Villa

20. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Find vacation rentals that suit your style

Top Shelter Island Hotel Reviews

Sun N Sound

Find out more about Shelter Island

Explore a world of travel with Expedia

Frequently asked questions

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