Lion Head Beach Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Lion Head Beach vacation rentals

Beach nearby

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 ￥17,858
￥43,214 total
includes taxes & fees
May 19 - May 20
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Lobby

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 ￥25,716
￥32,489 total
includes taxes & fees
May 19 - May 20
Montauk Manor
Flat-screen TV

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 ￥31,116
￥35,549 total
includes taxes & fees
May 19 - May 20
North Fork Resort
Smart TV, fireplace, books

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 ￥24,344
￥69,434 total
includes taxes & fees
May 18 - May 19
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
1 bedroom, bed sheets

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

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is ￥34,116
￥51,676 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is ￥34,116
￥51,676 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, desk, iron/ironing board, free WiFi

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 ￥21,685
￥43,134 total
includes taxes & fees
May 18 - May 19
The Stern at Soundview · Beach+Ocean+Sunrise
Apartment | Living area

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 ￥26,608
￥39,032 total
includes taxes & fees
May 19 - May 20
The Surf Club
Individually decorated, individually furnished, iron/ironing board

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 ￥27,016
￥35,183 total
includes taxes & fees
May 21 - May 22
Windward Shores Ocean Resort
Property grounds

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 ￥24,724
￥33,418 total
includes taxes & fees
May 18 - May 19
Driftwood Resort
Beach nearby, sun loungers, beach towels

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 ￥63,337
￥112,419 total
includes taxes & fees
May 30 - May 31
Beach Cottage, private beach and pass
Apartment | Iron/ironing board, free WiFi

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 ￥26,102
￥31,548 total
includes taxes & fees
May 19 - May 20
Montauk Oceanside Suites
1 bedroom, bed sheets

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
The price is ￥34,116
￥53,670 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Condo | Terrace/patio

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 ￥31,965
￥43,419 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums
Beach nearby

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 ￥28,437
￥70,154 total
includes taxes & fees
May 19 - May 20
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach nearby

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 ￥23,935
￥45,868 total
includes taxes & fees
May 18 - May 19
Keel at Soundview · Beach+OceanView+Sunrise
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
The price is ￥47,389
￥93,071 total
includes taxes & fees
May 22 - May 23
#35 - Beautiful 3 BR Beach Haven
Terrace/patio

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 ￥33,177
￥50,421 total
includes taxes & fees
May 21 - May 22
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop

Charming 1-bedroom apartment with AC in Sag Harbor

Charming 1-bedroom apartment with AC in Sag Harbor
Sag Harbor
The price is ￥46,431
￥94,761 total
includes taxes & fees
May 18 - May 19
Charming 1-bedroom apartment with AC in Sag Harbor
Dining

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 ￥51,273
￥203,411 total
includes taxes & fees
May 20 - May 21
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lion Head Beach Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"This is a beautiful place in a great town. Greenport has much to recommend it. Excellent restaurants, interesting shopping, and congenial places to hang around, have a drink, a pastry or coffee. The seafood, from shellfish to the top of the maritime food chain is fresh and abundant, and generally reasonably priced. The hotel provides a generous and varied continental breakfast buffet for its guests, and the staff is serious about hospitality with a smile. We very frankly now think of of the Harbor Front Inn as "our place in Greenport." "
Ira M 2-night trip
Posted 3 hours ago
The Harbor Front Inn

Find out more about Lion Head Beach

Search for holiday rentals in Lion Head Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Lion Head Beach using one of the methods below:

  • View our selection of featured holiday rentals in Lion Head Beach
  • Use the map to find apartments and other holiday homes in the Lion Head Beach neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lion Head Beach while they last

Look no further and take a look at our great range of rental properties in Lion Head Beach!

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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home rental outside of Lion Head Beach offers an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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

With 19 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 Railroad Museum of Long Island, 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.