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Lion Head Beach Holiday Rentals

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Our top choices for Lion Head Beach holiday rentals

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is NZ$290
includes taxes & fees
12 Oct - 13 Oct
Windward Shores Ocean Resort

2. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,413 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is NZ$291
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor

3. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (255 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is NZ$298
includes taxes & fees
12 Oct - 13 Oct
Driftwood Resort

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is NZ$541
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is NZ$519
includes taxes & fees
9 Oct - 10 Oct
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

6. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is NZ$259
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites

7. 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 NZ$2,258
includes taxes & fees
12 Oct - 13 Oct
Year round Jacuzzi - Blackberry East Hampton Home

8. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is NZ$493
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort

9. 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.
The price is NZ$717
includes taxes & fees
11 Oct - 12 Oct
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

10. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (302 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is NZ$491
includes taxes & fees
2 Nov - 3 Nov
The Surf Club

11. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Outstanding place"
United States
Michael H.
The price is NZ$475
includes taxes & fees
9 Oct - 10 Oct
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

12. 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 NZ$1,861
includes taxes & fees
19 Oct - 20 Oct
Spacious house in East Hampton with heated pool + WFH

13. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is NZ$886
includes taxes & fees
12 Oct - 13 Oct
Charming Accommodations in the Hamptons

14. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is NZ$437
includes taxes & fees
1 Nov - 2 Nov
Harbor Heights

15. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is NZ$439
includes taxes & fees
2 Nov - 3 Nov
The SandPiper

16. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is NZ$1,084
includes taxes & fees
12 Oct - 13 Oct
Unit 1311: Cottage | Garden View | Deuce

17. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is NZ$559
includes taxes & fees
12 Oct - 13 Oct
Aqua Vista

18. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is NZ$792
includes taxes & fees
3 Nov - 4 Nov
Beach Block Hideaway

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

Unit 811: Studio | 1st Floor-Garden View | Osprey
Napeague
10.0 out of 10, Exceptional, (1 review)
"Great stay. Unfortunately, they told us there was pickleball but there wasn’t. "
United States
Kevin C.
The price is NZ$876
includes taxes & fees
31 Oct - 1 Nov
Unit 811: Studio | 1st Floor-Garden View | Osprey

20. 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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is NZ$666
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lion Head Beach holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lion Head Beach. 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 Lion Head Beach. 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 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 holiday 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 Lion Head Beach short-term rentals, that won’t be hard to do.

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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Lion Head Beach is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 holiday rentals will I find in Lion Head Beach?

With 14 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 East End Seaport Maritime Museum, 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.