Lion Head Beach Vacation Rentals

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Sep 2 - Sep 3
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Sep 12 - Sep 14

Vacation Rentals in Lion Head Beach

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
A heated pool

2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!

10.0 out of 10, Exceptional, (89)
"It was a great stay"
2026 Full Summer or Monthly Available to Book, Huge Discounts for Early Booking!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1245)
"I had the best time and highly recommend this hotel!"
The price is ￥43,674
￥52,776 total
includes taxes & fees
Sep 29 - Sep 30
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (407)
"great place to stay"
The price is ￥24,179
￥29,224 total
includes taxes & fees
Oct 2 - Oct 3
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (239)
"Had a great time. Will be back"
The price is ￥48,811
￥62,162 total
includes taxes & fees
Sep 11 - Sep 12
Cliffside Resort Condominiums
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (275)
"Very close walk to the beach great for little ones "
The price is ￥32,920
￥45,608 total
includes taxes & fees
Sep 11 - Sep 12
The Surf Club
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (292)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is ￥22,061
￥28,408 total
includes taxes & fees
Sep 21 - Sep 22
Windward Shores Ocean Resort
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (230)
"Great place to stay for small family "
The price is ￥25,471
￥33,895 total
includes taxes & fees
Sep 24 - Sep 25
Driftwood Resort
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.8 out of 10, Excellent, (26)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is ￥25,830
￥59,779 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (70)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥33,086
￥54,224 total
includes taxes & fees
Oct 2 - Oct 3
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Offshore Residences
One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

4.0 star property
The price is ￥114,653
￥147,806 total
includes taxes & fees
Oct 1 - Oct 2
Offshore Residences
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (72)
"In the Hamptons working a Vintage market so I barely got to enjoy this incredibly gorgeous home, but it was perfect for just me and the host were absolutely delightful so friendly and accommodating they even let me sleep in which I haven’t had a chance to do in sometime so that was much appreciated I rested better than I have in months in this sweet cottage on a beautiful property. They made sure I was taken care of while giving me speciation enjoy some much needed quiet time. It’s a stunning...
Fairy Tale Guest Cottage in Magic Garden by Pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is ￥10,242
￥27,369 total
includes taxes & fees
Sep 3 - Sep 4
The Stern at Soundview · Beach+Ocean+Sunrise
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
2 bedrooms, iron/ironing board, free WiFi, bed sheets

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Terrace/patio

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is ￥10,622
￥27,805 total
includes taxes & fees
Sep 3 - Sep 4
The Mast at Soundview · Beach+Ocean+Sunrise
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

9.0 out of 10, Wonderful, (2)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
The price is ￥26,478
￥33,949 total
includes taxes & fees
Sep 3 - Sep 4
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
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

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great location ,beautiful hotel,nice staff"
ROBERT 1-night trip
Posted 9 days ago
The Harbor Front Inn
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"
christine 2-night trip
Posted 2 weeks ago
Sound View Greenport

Find out more about Lion Head Beach

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:

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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?

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen: This Lion Head Beach vacation home rental is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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

With 17 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.