Lion Head Beach Vacation Rentals from CA $232: Short-Term Rentals for 2026

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Our top choices for Lion Head Beach vacation rentals

1. Windward Shores Ocean Resort

Napeague

Banessa

CA $253 total

includes taxes & fees

Oct 29 - Oct 30

2. Driftwood Resort

Montauk

Julian

CA $232 total

includes taxes & fees

Oct 30 - Oct 31

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

3. Montauk Manor

Montauk

Maria

CA $261 total

includes taxes & fees

Nov 17 - Nov 18

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

4. Cliffside Resort Condominiums

Greenport

William

CA $426 total

includes taxes & fees

Nov 12 - Nov 13

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

5. North Fork Resort

Greenport

Altynai

CA $497 total

includes taxes & fees

Nov 1 - Nov 2

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

6. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

CA $2,047 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

7. Spacious house in East Hampton with heated pool + WFH

East Hampton

ANGELA S.

CA $1,909 total

includes taxes & fees

Nov 4 - Nov 5

8. Montauk Oceanside Suites

Downtown Montauk

Jadana

CA $242 total

includes taxes & fees

Nov 2 - Nov 3

A spacious living area with a large bed, a dining table, and a kitchen in the background.

9. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Napeague

Liana T.

CA $587 total

includes taxes & fees

Oct 28 - Oct 29

10. The Surf Club

Montauk

na

CA $438 total

includes taxes & fees

Nov 4 - Nov 5

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

11. Charming Accommodations in the Hamptons

Sag Harbor

CA $714 total

includes taxes & fees

Nov 2 - Nov 3

A sunroom with a large sectional sofa, a small table, and a view of the beach and hills.

12. Unit 511: Cottage | Ocean View | Nautilus

Napeague

Steven B.

CA $1,097 total

includes taxes & fees

Oct 28 - Oct 29

A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.

13. Offshore Spa & Residences

Downtown Montauk

"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...

Frank

CA $496 total

includes taxes & fees

Nov 9 - Nov 10

A wooden deck with a table and chairs, a wicker chair, and a toilet.

14. Unit 721: Two-Bedroom | 2nd Floor-Ocean View | Sand Dollar

Napeague

CA $798 total

includes taxes & fees

Oct 28 - Oct 29

A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

15. Harbor Heights

Pipes Cove

Steven R.

CA $337 total

includes taxes & fees

Nov 4 - Nov 5

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

16. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

Katie B.

CA $822 total

includes taxes & fees

Nov 8 - Nov 9

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.

CA $1,555 total

includes taxes & fees

Oct 29 - Oct 30

A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

18. Aqua Vista

Pipes Cove

Kerri L.

CA $357 total

includes taxes & fees

Nov 9 - Nov 10

A patio area with wicker chairs and a table, surrounded by gravel and plants.

19. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

CA $429 total

includes taxes & fees

Oct 28 - Oct 29

A covered patio with outdoor furniture, a door, and a view of a residential area.

20. The SandPiper

Pipes Cove

Manuela C.

CA $340 total

includes taxes & fees

Nov 10 - Nov 11

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Top Lion Head Beach Hotel Reviews

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."

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 Lion Head Beach

Everything you need to know about Lion Head Beach 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 Lion Head Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Lion Head Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lion Head Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lion Head Beach. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lion Head Beach vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lion Head Beach vacation rentals we have selected for you start as low as CA $232 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lion Head Beach rentals

At Expedia, we put the best Lion Head Beach 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 Lion Head Beach 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 Lion Head Beach 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 Lion Head Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Lion Head Beach?

Yes, you can find vacation rentals close to well known sights in Lion Head Beach, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Lion Head Beach has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental outside of Lion Head Beach 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 will I find in Lion Head Beach?

With 14 Expedia vacation rentals, you're sure to find just the right place for your Lion Head Beach stay.

What’s there to see and do in Lion Head Beach?

Explore the area and family-friendly sights such as East End Seaport Maritime Museum, or get out into nature at a spot like The Hamptons Beaches. In the larger area, you’ll find Pollock-Krasner House and Study Center and LongHouse Reserve.

What’s a vacation rental in Lion Head Beach like?

Vacation rentals are private properties you can book for a couple of days or more in Lion Head Beach. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Lion Head Beach vacation rentals

1. Windward Shores Ocean Resort

2. Driftwood Resort

3. Montauk Manor

4. Cliffside Resort Condominiums

5. North Fork Resort

6. Year round Jacuzzi - Blackberry East Hampton Home

7. Spacious house in East Hampton with heated pool + WFH

8. Montauk Oceanside Suites

9. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

10. The Surf Club

11. Charming Accommodations in the Hamptons

12. Unit 511: Cottage | Ocean View | Nautilus

13. Offshore Spa & Residences

14. Unit 721: Two-Bedroom | 2nd Floor-Ocean View | Sand Dollar

15. Harbor Heights

16. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

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

18. Aqua Vista

19. American Beech in Greenport - Petite King Room 7

20. The SandPiper

Find vacation rentals that suit your style

Top Lion Head Beach Hotel Reviews

Zey Hotel

Offshore Montauk

Gurney's Montauk Resort & Seawater Spa

The Bentley Hotel Southampton

Montauk Blue Hotel

Marram

Ocean Vista Resort

Faraway Sag Harbor

Ocean Surf Resort

Find out more about Lion Head Beach

Frequently asked questions

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