Lion Head Beach Vacation Rentals from $173: Search Short-Term Rentals

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Our top choices for Lion Head Beach vacation rentals

1. Windward Shores Ocean Resort

Napeague

Banessa

$161 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

2. Montauk Manor

Montauk

Maria

$163 nightly

Nov 17 - Nov 18

Total with taxes and fees

3. Driftwood Resort

Montauk

Julian

$166 nightly

Oct 30 - Oct 31

Total with taxes and fees

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

4. Year round Jacuzzi - Blackberry East Hampton Home

East Hampton

Suzanne R.

$1,194 nightly

Oct 25 - Oct 26

Total with taxes and fees

A balcony with a view of the sea, a dining table, and a blue house in the background.

5. Cliffside Resort Condominiums

Greenport

William

$266 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Napeague

Liana T.

$368 nightly

Oct 25 - Oct 26

Total with taxes and fees

7. Montauk Oceanside Suites

Downtown Montauk

Jadana

$151 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

8. Charming Accommodations in the Hamptons

Sag Harbor

$443 nightly

Oct 26 - Oct 27

Total with taxes and fees

9. The Surf Club

Montauk

na

$274 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

10. The SandPiper

Pipes Cove

Manuela C.

$223 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.

11. 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.

12. Harbor Heights

Pipes Cove

Steven R.

$213 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

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

East Hampton

ANGELA S.

$937 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

14. North Fork Resort

Greenport

Altynai

$296 nightly

Oct 27 - Oct 28

Total with taxes and fees

A coastal hotel with multiple buildings, a swimming pool, and a beach view.

15. Unit 823: Studio | 2nd Floor-Ocean View | Osprey

Napeague

Dianna L.

$368 nightly

Oct 25 - Oct 26

Total with taxes and fees

16. Unit 1011: Studio | 1st Floor-Garden View | Starfish

Napeague

Mark F.

$368 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

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

Pipes Cove

"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"

Nino

$311 nightly

Nov 2 - Nov 3

Total with taxes and fees

18. Unit 1012: Studio | 1st Floor-Garden View | Starfish

Napeague

$368 nightly

Oct 25 - Oct 26

Total with taxes and fees

19. Unit 1023: Studio | 2nd Floor-Pool View | Starfish

Napeague

Michael M.

$368 nightly

Oct 25 - Oct 26

Total with taxes and fees

20. Unit 811: Studio | 1st Floor-Garden View | Osprey

Napeague

Kevin C.

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Top Lion Head Beach Hotel Reviews

Montauk Yacht Club

10/10 Excellent

"Excellent hotel, clean and spacious rooms, friendly and attentive staff."

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."

Zey Hotel

10/10 Excellent

"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly and accommodating. We had a great time checking out all the cool lounge areas in the hotel. The room was clean and charming as well. Would definitely stay here again the next time we visit Greenport"

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

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, 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 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 low season months. For more hustle and bustle, you may prefer to visit Lion Head Beach 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 $173 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 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. Montauk Manor

3. Driftwood Resort

4. Year round Jacuzzi - Blackberry East Hampton Home

5. Cliffside Resort Condominiums

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

7. Montauk Oceanside Suites

8. Charming Accommodations in the Hamptons

9. The Surf Club

10. The SandPiper

11. Aqua Vista

12. Harbor Heights

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

14. North Fork Resort

15. Unit 823: Studio | 2nd Floor-Ocean View | Osprey

16. Unit 1011: Studio | 1st Floor-Garden View | Starfish

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

18. Unit 1012: Studio | 1st Floor-Garden View | Starfish

19. Unit 1023: Studio | 2nd Floor-Pool View | Starfish

20. Unit 811: Studio | 1st Floor-Garden View | Osprey

Find vacation rentals that suit your style

Top Lion Head Beach Hotel Reviews

Montauk Yacht Club

Faraway Sag Harbor

Montauk Blue Hotel

The Bentley Hotel Southampton

Zey Hotel

Ocean Surf Resort

Sag Harbor Inn

The Harbor Front Inn

The Atlantic Hotel

Find out more about Lion Head Beach

Frequently asked questions

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