Windward Shores Amagansett Amenities photoWindward Shores Amagansett Exterior photoWindward Shores Amagansett Room photo

Book Windward Shores - Premium Seaview Hotel in Amagansett

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Check rooms and rates
From$178 /night
Check-in
30May
Check-out
31May
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

2062 Montauk Hwy, Amagansett, true
-
Close to Napeague Beach
Great
8.3
8.9
/10
4.0
4.2
/5

Accommodations

Each accommodation at Windward Shores includes a fully equipped kitchen and dining area, plus a living area with a flat-screen cable TV. The spacious units offer a private patio and loft-style designs with unique layouts across two floors. Some rooms provide ocean views from private balconies and decks, with daily housekeeping included.

Beach & Pool

The resort offers direct access to a private, soft-sand beach with seasonal cabana service and beach setup assistance from staff like John. An outdoor heated swimming pool with a fence around it is open seasonally, surrounded by meticulously maintained grounds. The pool area features a sun terrace and views of the landscaped garden.

Recreation & Amenities

Two tennis courts are available for guest use, and tennis equipment is provided. Fishing and golf are accessible nearby, with Maidstone Golf Club 13 minutes away. A shared lounge/TV area, vending machines, and a terrace with ocean breezes round out the common spaces.

Location

Windward Shores sits on 5 acres of landscaped grounds directly on the ocean and adjacent to Napeague Harbor. Montauk is an 8-minute drive, and East Hampton is 10 minutes away, with the resort located along Montauk Point State Parkway. Montauk Point State Park and East Hampton Village attractions are within a short drive.

Family-Friendly Amenities

Family rooms are available, and the resort provides child-friendly amenities such as a fenced outdoor pool and spacious two-bedroom loft units with separate bathrooms on each level. Daily housekeeping and easy parking simplify family stays. The property offers a quiet, nature-rich environment with direct beach access for children to explore safely.

Highlights

Accommodations: Loft-style units with full kitchens and private patios

Beach Access: Direct path to a private oceanfront beach with cabana service

Recreation: Two tennis courts, heated pool, fishing and golf nearby

Location: 8 minutes from Montauk, 10 minutes from East Hampton

Grounds: 5-acre landscaped property with garden and sun terrace

Ideal for: Families, couples seeking a quiet beach getaway

“Windward Shores sits in a beautifully maintained spot, close enough to Montauk's energy but offering a genuine sense of peace. The grounds feel cared for, and stepping onto the private beach for a sunrise is quite something. My room was clean and well-appointed, making for a comfortable stay despite the short drive to town.”
Hotel logo
James DavidEditor-in-Chief at Seaviewhotels

Select your room type

Windward Shores offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
  • Studio
    2 persons
    34 sq. feet
    1 King-size bed
    Air conditioning
    Heating
  • Deluxe Studio
    2 persons
    34 sq. feet
    1 King-size bed
    Air conditioning
    Heating
  • King Studio
    2 persons
    1 King-size bed
    Air conditioning
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!
May 2026 - May 2027
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Check-in/ Check-out

Facilities

Windward Shores offers amenities for your comfortable stay and unforgettable experiences
Facilities: Great
8.4/10Review score

General

  • No smoking on site
  • Free Wi-Fi in public areas
  • Parking
  • No pets allowed
  • Vending machines

Sports & Fitness

  • Tennis court
  • Golf course
  • Fishing

Guest Parking

  • Dryer
  • Cookware/ Kitchen utensils

Services

  • Housekeeping
  • Laundry

Dining

  • Outdoor dining area

Spa & Leisure

  • Seasonal outdoor pool
  • Heated swimming pool
  • Beach access
  • Sun terrace
  • Garden area
  • Leisure/ TV room

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Dressing area
  • Patio
  • Terrace
  • Dining table

Self-catering

  • Dryer
  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV
  • AM/FM alarm clock

Room decor

  • Carpeted floor
Show more

Windward Shores Location

2062 Montauk Hwy, Amagansett, true
Explore Amagansett
Local Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Montauk Point Lighthouse
5-minute drive
Historic lighthouse with stunning views; offers guided tours and a museum showcasing maritime history.
Hither Hills State Park
7-minute drive
Spacious park featuring hiking trails and sandy beaches; ideal for picnics and outdoor activities.
Napeague Beach
18 minutes walking
Pristine beach known for its tranquil environment and excellent surfing conditions; perfect for sunbathing.
Victor D'Amico Institute of Art
20-minute walk
Art institute focusing on creative education; hosts various exhibitions and workshops throughout the year.
Discover the local attractions near Windward Shores
Uncover a selection of notable attractions near Windward Shores offering various experiences in Amagansett
Ideal for relaxing beach days: Napeague Beach
Great for outdoor adventures and picnics: Theodore Roosevelt County Park
Perfect for scenic hikes and nature walks: Walking Dunes
Well suited for nature enthusiasts and wildlife viewing: Napeague State Park
Suited for art lovers and cultural exploration: Victor D'Amico Institute of Art
Best for family-friendly recreational activities: Hither Hills State Park
Works well for kayaking and tranquil sunsets: Napeague Bay
Surfing at Napeague Beach
18 minutes walking
Popular spot for surfing with rentals available nearby; suitable for all skill levels, especially in summer.
Hiking in Hither Hills State Park
7-minute drive
Scenic trails with beautiful landscapes and wildlife; great for nature lovers and offers varied difficulty levels.
Yoga Classes
10-minute drive
Local studios offering classes for all levels; ideal for relaxation and rejuvenation during your stay.
Lobster Roll Restaurant
11 minutes walking
Casual eatery specializing in fresh seafood and lobster rolls; known for its laid-back atmosphere.
The Lobster Roll
11 minutes walking
Beloved local spot for lobster rolls and chowder; hearty portions and friendly service.
Amagansett Farmers Market
5-minute drive
Offers fresh local produce and artisanal goods; ideal for a light lunch or snacks; seasonal operation.
The Surf Lodge
10-minute drive
Vibrant bar and restaurant with live music and events, offering a lively atmosphere for nightlife enthusiasts.
Montauk Playhouse
15-minute drive
Community center with events ranging from film screenings to theater productions; suitable for all ages.
Getting around
  • City Centre
    Amagansett 14 min  ·  5.6 mi
  • Airports
    Long Island MacArthur (ISP) 147 min  ·  60.8 mi
    Tweed-New Haven (HVN) 238 min  ·  98.4 mi
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Property information and rules
Check-in
from 16:00-17:00
Check-out
until 11 am
Guest Parking
Private parking is possible at a location nearby for free.
Internet
Wireless internet is available in public areas for free.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are not allowed.
Number of rooms:
77

Reviews and Ratings

Feedback about Windward Shores from previous guests about their experience.
Review score
Based on 85 verified reviews
8.2 /10
Great
77 %
Recommend
Breakfast
7.5/10
Cleanliness
8.3/10
Comfort
8.4/10
Facilities
8.4/10
Free WiFi
7.5/10
Location
8.8/10
Paid Wi-Fi
10.0/10
Staff
8.8/10
Value for money
7.8/10
Pros
Beach proximity
Quiet location
Helpful staff
Room size
Cons
Dated furnishings
Maintenance issues
Cleanliness concerns
Sound insulation
Guest reviews
based on 93 reviews
8.3/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews
FAQs
About Windward Shores
What time is check-in and check-out at Windward Shores?
Check-in is at 16:00 and check-out is at 11:00.
Is there parking available at Windward Shores?
Private parking is available on-site for free, but a reservation is needed.
What recreational facilities are available at Windward Shores?
The resort features two tennis courts, a seasonal outdoor heated pool, and direct beach access.
What room amenities are provided at Windward Shores?
Each unit includes a fully equipped kitchen, a living area with a flat-screen cable TV, and a private patio.
What attractions are near Windward Shores?
Nearby attractions include Montauk Point State Park (8 km), East Hampton Village (10 km), and Maidstone Golf Club (15 km).
How far is Windward Shores from the nearest airport?
Windward Shores is approximately 15 km from East Hampton Airport.
What services are provided at Windward Shores?
The hotel offers complimentary Wi-Fi throughout the property and seasonal cabana service at the beach.
Are there activities for families at Windward Shores?
The resort provides family-friendly amenities such as beach access and recreational facilities.

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