Lion Head Beach Hotels from S$171

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19 Dec - 20 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Lion Head Beach hotels

Front of property – evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1269)
Unwind at this Italian-inspired aparthotel offering both indoor and outdoor swimming. Enjoy Monte's dining, 24-hour fitness centre, and in-room kitchenettes. Located minutes from Montauk Station with Shadmoor State Park and Fort Pond nearby.
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is S$230
includes taxes & fees
13 Jan - 14 Jan, 2026
Montauk Manor
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (878)
Located near Montauk Station, this welcoming motel features a seasonal outdoor pool and garden terrace. Explore neighbouring hiking and biking trails or visit Montauk Marine Basin and Gin Beach. Guests praise the helpful staff, clean rooms, free WiFi and parking.
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
Experience coastal luxury at this oceanfront hotel with direct beach access and scenic vistas. Enjoy American fare at The Halyard restaurant or drinks at one of 3 bars including a poolside option. The seasonal outdoor pool, free breakfast, and attentive staff create an idyllic Greenport retreat.
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is S$298
includes taxes & fees
1 Jan - 2 Jan, 2026
Sound View Greenport
Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (228)
Discover coastal charm at this waterfront Southold retreat offering free bicycles for exploring nearby wineries. Unwind with drinks at the bar after a day visiting The Old Field Vineyards or relaxing at Crescent Beach, all while enjoying attentive service from the friendly staff.
"Room was clean and comfortable. Easy check in and check out. Staff very accommodating. "
United States
James
The price is S$233
includes taxes & fees
21 Dec - 22 Dec
The Shoals Suites and Slips
View from room
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
This Montauk motel offers beachside relaxation with spa services and a welcoming bar/lounge. Surrounded by gardens and featuring a lovely terrace, it provides free WiFi and parking near Second House Museum and Kirk Park Beach.
"Great weekend trip "
United States
Timothy
The price is S$342
includes taxes & fees
28 Dec - 29 Dec
Hero Beach Club
View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
Set along the waterfront in Greenport, this charming hotel offers a tranquil retreat with easy access to the local train station. Enjoy a refreshing dip in the seasonal outdoor pool or maintain your workout routine at the 24-hour fitness centre.
"Awesome stay!!! Great Location "
United States
Bryan
The price is S$261
includes taxes & fees
22 Dec - 23 Dec
The Harbor Front Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (443)
This charming Southampton motel offers a peaceful garden and terrace. Enjoy easy access to Shinnecock Hills Golf Course while rooms provide convenient refrigerators and microwaves. Hiking trails, kayaking, and free WiFi enhance your stay near scenic beaches.
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is S$171
includes taxes & fees
1 Jan - 2 Jan, 2026
Hamlet Inn
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
Escape to this guesthouse on Chase Creek, where a serene golf course setting meets waterfront tranquility. Enjoy convenient self parking and WiFi, plus a welcoming terrace. Shelter Island Country Club and Sylvester Manor await nearby.
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is S$154
includes taxes & fees
6 Jan - 7 Jan, 2026
House on Chase Creek
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
Escape to this Wainscott retreat featuring free WiFi and parking. Located only 5 minutes from pristine Hamptons shorelines and Wolffer Estates Vineyard. The attentive staff receives consistent praise while the refreshing outdoor pool enhances summer stays.
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is S$276
includes taxes & fees
22 Dec - 23 Dec
The Sagaponack
Exterior
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
Set in charming Greenport, this inn offers a restaurant, bar, and free breakfast to start your day. Borrow bicycles to explore nearby attractions like Greenport Harbour Brewing Company, or stroll 8 minutes to the train station. Helpful staff and garden views await.
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is S$316
includes taxes & fees
21 Dec - 22 Dec
American Beech Hotel
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (398)
This welcoming hotel offers free WiFi and parking just 15 minutes from The Hamptons Beaches. Enjoy the seasonal outdoor pool after exploring nearby attractions like Sebonack and Shinnecock Hills golf courses, with water activities moments away.
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is S$186
includes taxes & fees
4 Jan - 5 Jan, 2026
The Bentley Hotel Southampton
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
Southampton
8.6 out of 10, Excellent, (549)
Experience coastal charm at this Tudor-style inn with a seasonal pool and tennis court. Just 5 minutes from Hamptons beaches and walking distance to shops and restaurants. Claude's serves local cuisine while 3 bar options enhance the quiet, family-friendly atmosphere.
"Such a great location!"
United States
Elizabeth
The price is S$316
includes taxes & fees
1 Jan - 2 Jan, 2026
Southampton Inn
Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (81)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is S$245
includes taxes & fees
1 Jan - 2 Jan, 2026
Offshore Montauk
Exterior
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (160)
Exploring the Hamptons is effortless from this charming hotel with complimentary breakfast and bicycle rentals. Just minutes from beautiful beaches and the Amelia Cottage Museum, guests can relax in the seasonal outdoor pool or garden.
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Outdoor pool, pool loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (288)
Discover a charming coastal retreat with a seasonal pool and complimentary bicycles to explore Montauk's natural beauty. Just a quick drive from South Edison Beach and Montauk Point, this hotel offers convenient access to hiking trails and water activities.
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
Daunt's Albatross Motel
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (576)
Relax at this waterside Sag Harbour hotel with an inviting outdoor pool and complimentary continental breakfast. Just minutes from The Hamptons Beaches and the Whaling Museum, enjoy free WiFi and parking while exploring the charming coastal village.
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is S$317
includes taxes & fees
21 Dec - 22 Dec
Sag Harbor Inn
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
Soak in bay vistas at this Greenport beach hotel with 2 bars and 3 dining options. After a massage at the full-service spa, grab a complimentary bike to explore nearby Railway Museum and East End Seaport Maritime Museum.
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (975)
Situated by the ocean with outdoor tennis courts and a swimming pool, this Southampton hotel is close to food and shopping. Convenient to Sebonack and Shinnecock Hills Golf Course, with free WiFi and parking. Guests praise the helpful staff.
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (203)
This Southampton hotel offers a convenient home base with free WiFi and parking. Located within a 10-minute drive of Cooper's Beach, guests can enjoy the outdoor pool after exploring nearby attractions and the cultural museum.
"Good location. Nice people!! "
United States
Theresa
The price is S$183
includes taxes & fees
18 Jan - 19 Jan, 2026
Southampton Long Island Hotel
Garden
The Maidstone

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (150)
Just 5 minutes from The Hamptons Beaches, this East Hampton boutique hotel serves free breakfast and offers complimentary bikes to explore the area. Enjoy the restaurant, garden setting, and beach shuttle, plus free WiFi and parking near local attractions.
"We had a wonderful stay "
United States
Sabrina
The price is S$421
includes taxes & fees
21 Dec - 22 Dec
The Maidstone
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing "
olivia 1-night trip
Posted 4 days ago
The Bentley Hotel Southampton

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Heated Pool Hot tub Beachwood Cove by Rovetravel

Heated Pool Hot tub Beachwood Cove by Rovetravel

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Frequently asked questions

What's the best place for a stay in Lion Head Beach?
Gurney's Montauk Resort & Seawater Spa, located 9.6 mi (15.4 km) from the heart of Lion Head Beach, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Sound View Greenport and Montauk Blue Hotel. See all available top hotels, or vacation rentals in Lion Head Beach.
If I need to cancel my hotel reservation in Lion Head Beach, will I receive a refund?
Yes, the majority of room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Lion Head Beach.
What are some hotels with pools in Lion Head Beach?
Gurney's Montauk Resort & Seawater Spa: Offers a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport and Montauk Blue Hotel are two additional hotels with an on-site pool. View all hotels with pools in Lion Head Beach.
What is staying in Lion Head Beach like?
Those travelling to Lion Head Beach will definitely enjoy the sights to see and things to do. In Lion Head Beach, there are 19 hotels and other accommodation options to choose from. Find out more about Lion Head Beach.
What are the top places to visit in Lion Head Beach?
A favourite place to visit is The Hamptons Beaches. You'll also find Pollock-Krasner House and Study Center and LongHouse Reserve in the area. Take a look at what more there is to see and do in Expedia's Lion Head Beach guide.
What's the seasonal weather like in Lion Head Beach?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Lion Head Beach is 1443 mm.

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