Holiday Rentals in Lion Head Beach

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Our top choices for Lion Head Beach holiday rentals

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (56 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is €236
includes taxes & fees
19 May - 20 May
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is €176
includes taxes & fees
19 May - 20 May
Montauk Manor

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is €238
includes taxes & fees
20 May - 21 May
North Fork Resort

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is €382
includes taxes & fees
18 May - 19 May
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is €281
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is €281
includes taxes & fees
25 May - 26 May
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €241
includes taxes & fees
25 May - 26 May
The Stern at Soundview · Beach+Ocean+Sunrise

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is €212
includes taxes & fees
19 May - 20 May
The Surf Club

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is €196
includes taxes & fees
21 May - 22 May
Windward Shores Ocean Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (238 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is €181
includes taxes & fees
19 May - 20 May
Driftwood Resort

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is €613
includes taxes & fees
30 May - 31 May
Beach Cottage, private beach and pass

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is €171
includes taxes & fees
19 May - 20 May
Montauk Oceanside Suites

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is €235
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is €383
includes taxes & fees
19 May - 20 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
The price is €257
includes taxes & fees
25 May - 26 May
Keel at Soundview · Beach+OceanView+Sunrise

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
#35 - Beautiful 3 BR Beach Haven

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €275
includes taxes & fees
21 May - 22 May
American Beech in Greenport - Petite King Room 7

Charming 1-bedroom apartment with AC in Sag Harbor

Charming 1-bedroom apartment with AC in Sag Harbor
Sag Harbor
The price is €504
includes taxes & fees
18 May - 19 May
Charming 1-bedroom apartment with AC in Sag Harbor

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is €1,101
includes taxes & fees
20 May - 21 May
BlackBerry Private home with jacuzzi yearlong
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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Top Lion Head Beach Hotel Reviews

Find out more about Lion Head Beach

Everything you need to know about Lion Head Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lion Head Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lion Head Beach holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lion Head Beach holiday rentals we have selected for you start as low as €171 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 holiday 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 holiday.

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 holiday rentals in Lion Head Beach?

Yes, there are holiday rentals close to the most popular sights in Lion Head Beach, or you can select a more secluded option if you're looking for a relaxing stay.

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

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Lion Head Beach offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Lion Head Beach?

With 19 Expedia holiday rentals, you're guaranteed 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 Railroad Museum of Long Island, or get out into nature at a spot like The Hamptons Beaches. In the wider area, you’ll find Pollock-Krasner House and Study Center and LongHouse Reserve.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Lion Head Beach. Holiday rentals feature extras such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.