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Lion Head Beach Vacation Rentals

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Our top choices for Lion Head Beach vacation rentals

1. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
Driftwood Resort

2. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (331 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is CA $184
CA $248 total
includes taxes & fees
Nov 2 - Nov 3
Windward Shores Ocean Resort

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,419 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is CA $194
CA $249 total
includes taxes & fees
Nov 30 - Dec 1
Montauk Manor

4. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 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 CA $134
CA $1,933 total
includes taxes & fees
Nov 8 - Nov 9
Year round Jacuzzi - Blackberry East Hampton Home

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $236
CA $425 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums

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

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

7. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (458 reviews)
"Quiet lodging,comfortable, everything you need, a stone’s throw from the ocean. Great accommodation. All check in done on line as well as the cleaning concerns. This was new to me and took a little adjustment."
United States
kathleen
The price is CA $190
CA $232 total
includes taxes & fees
Nov 5 - Nov 6
Montauk Oceanside Suites

8. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
The price is CA $305
CA $437 total
includes taxes & fees
Nov 5 - Nov 6
The Surf Club

9. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is CA $314
CA $730 total
includes taxes & fees
Nov 2 - Nov 3
Charming Accommodations in the Hamptons

10. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $119
CA $322 total
includes taxes & fees
Nov 10 - Nov 11
Harbor Heights

11. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is CA $119
CA $322 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (51 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is CA $133
CA $356 total
includes taxes & fees
Nov 17 - Nov 18
Aqua Vista

13. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (71 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $434
CA $496 total
includes taxes & fees
Nov 9 - Nov 10
North Fork Resort

14. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 reviews)
"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...
United States
Frank
The price is CA $363
CA $495 total
includes taxes & fees
Dec 1 - Dec 2
Offshore Spa & Residences

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

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is CA $182
CA $512 total
includes taxes & fees
Nov 2 - Nov 3
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is CA $1,029
CA $2,018 total
includes taxes & fees
Nov 3 - Nov 4
Spacious house in East Hampton with heated pool + WFH

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

Unit 823: Studio | 2nd Floor-Ocean View | Osprey
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"Loved having coffe on the deck enjoying the views. The location was perfect for us. Hope to be back!"
United States
Dianna L.
Unit 823: Studio | 2nd Floor-Ocean View | Osprey

18. Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side

Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side
Napeague
10.0 out of 10, Exceptional, (1 review)
"Great"
United States
Anonymous traveller
Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side

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

Unit 1011: Studio | 1st Floor-Garden View | Starfish
Napeague
10.0 out of 10, Exceptional, (1 review)
"We very much enjoyed our stay, would definitely book again. "
United States
Mark F.
Unit 1011: Studio | 1st Floor-Garden View | Starfish

20. Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (1 review)
"Loved the unit and the grounds! Everything was as in description & super friendly staff!"
United States
cathleen f.
Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lion Head Beach. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.