Windward Shores | Resort in Amagansett

Q: How much does it cost per night to stay in Windward Shores?

Best-rates for the Windward Shores starts from $317 per night with includes Air Conditioner, Parking, Pool, Designated Smoking Area, TV, View, Ocean View, Balcony/Terrace, Oceanfront, Security/Safety, Sports/Activities, Fireplace/Heating, Guest Services, Entertainment, Child Friendly, Internet, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

| 8.4 (90 Reviews) | 34 Bathrooms 379 Guests Stay&Play

Resort in Napeague, Amagansett

On 5 acres of landscaped grounds, this oceanfront resosrt is adjacent to Napeague Harbor, a 10-minute drive from East Hampton. It features 2 tennis courts, an outdoor pool and free Wi-Fi. Montauk is a 10-minute drive. A full kitchen and dining area is provided in every accommodations at Windward Shores Ocean Resort. The spacious units include a living area with a flat-screen cable TV. Units also offer a private patio. Seasonal cabana service is available at this resort. Resort Windward Shores is conveniently located along Montauk Point State Parkway. It is a 15-minute drive from East Hampton Airport, and a 13-minute drive from Maidstone Golf Club.

Windward Shores is located in Amagansett.

This 77 Bedrooms Resort is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Air Conditioner, Parking, Pool, and several others. This is a 3 star rated property and has over 90 reviews with the average score of 8.4 . Coming to Amagansett and needing a place to stay? Be it for work or for leisure, consider staying at this Resort for your next visit, you will surely love it.

You can check the reviews and description of this 77 Bedrooms Resort if you want to learn more about this StayAndPlay.com place in Amagansett. These details are authentic, as they are provided by our partner, booking.com.

This Windward Shores in Amagansett is well equipped and has all facilities that have been listed below. Please note that these details were shared to us by booking.com for the listed “Windward Shores”. We solely rely on their shared details and are regarded as “accurate”. If you have any concerns about the information or accuracy describing this Resort, please let us know.

Unique Amenities

Air Conditioner
Parking
Pool
Designated Smoking Area
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Fireplace/Heating
Guest Services
Entertainment
Child Friendly
Internet
Laundry

Policies

Check-in The minimum age for check-in is 21

Cancellation policy Non refundable

Pet Policy Pets are not allowed

Other Policy Upon check-in photo identification and credit card are required. all special requests are subject to availability upon check-in. special requests cannot be guaranteed and may incur additional charges, office hours may vary; please call the hotel by 5 pm for any questions.guests are required to show a photo id and credit card upon check-in. please note that all special requests are subject to availability and additional charges may apply.

2062 Montauk Highway, Amagansett, NY 11930, USA

What Our Guests say 500 + Reviews

Jun 8, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Kym, USA

May 31, 2026 07:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Charles, USA

May 28, 2026 07:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Winter, United Kingdom

May 22, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Location

Negative: Furniture worn

Summary: Good overall

William, USA

Apr 22, 2026 07:00:00 AM

Reviewer Type: Extended Group

Travel Purpose: leisure

Positive: The corner 2 bed apartment right on the beach you’re couldn’t fault

Negative: The decor felt low-quality compared to the rest of the accommodation. The lighting was harsh, with very bright white bulbs that made the space uncomfortable. The curtains didn’t properly fit the patio door, and the blinds seemed very cheap. There was no headboard, which made the room feel unfinished. The duvet appeared worn and wasn’t covered with a proper duvet cover or sheets, which was off-putting.

Summary: The location and space was incredible, but they have cut corners with the decor - felt like cheap Walmart

David, USA

Apr 9, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Louise, Ireland

Mar 30, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Vahid, Iran, Islamic Republic of

Mar 30, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: The 2 bedrooms and 2 bathrooms

Negative: The cost was excessive

Summary: Clean, comfortable facilities

anne CHERYL, Australia

Nov 24, 2025 08:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Eleni, USA

Nov 22, 2025 08:00:00 AM

Reviewer Type: Family With Children

Travel Purpose: leisure

Jodie, USA

FAQ's

Is this Windward Shores pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

What time is check-in & check-out at Windward Shores?

Check-in time for Windward Shores starts counting from 4:00 PM and check-out is until 11:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Does the Windward Shores have a swimming pool?

Yes, this Windward Shores has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Windward Shores?

Best-rates for the Windward Shores starts from $317 per night with includes Air Conditioner, Parking, Pool, Designated Smoking Area, TV, View, Ocean View, Balcony/Terrace, Oceanfront, Security/Safety, Sports/Activities, Fireplace/Heating, Guest Services, Entertainment, Child Friendly, Internet, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Windward Shores a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this resort 3 stars or guests have recommended them suitable for families. As reported by the owner or manager, the resort has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Windward Shores wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Windward Shores has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Windward Shores?

Based on the information reported by the owner or manager, the Windward Shores indicates 1 day stay policy at this resort. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Windward Shores?

Based on the information reported by the owner or manager, details for the cancellation policy for the Windward Shores are as follows: Non refundable Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check Resort Availability

Nightly rates from:

US $317