Napeague Rentals USA New York Amagansett Napeague

Windward Shores | Resort in Amagansett

| 8.3 (96 Reviews) |  34 Bathrooms  379 Guests
Napeague Resort | Windward Shores

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, Ocean View, Oceanfront, and several others. This is a 3 star rated property and has over 96 reviews with the average score of 8.3 . 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 PickleTrip 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.

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2062 Montauk Highway, Amagansett, NY 11930, USA

Amenities

Air ConditionerAir Conditioner
ParkingParking
PoolPool
Designated Smoking AreaDesignated Smoking Area
TVTV
ViewView
Ocean ViewOcean View
Balcony/TerraceBalcony/Terrace
OceanfrontOceanfront
Security/SafetySecurity/Safety
Sports/ActivitiesSports/Activities
Fireplace/HeatingFireplace/Heating
Guest ServicesGuest Services
EntertainmentEntertainment
Child FriendlyChild Friendly
InternetInternet
LaundryLaundry

Facility Overview

ParkingParking
  • Private ParkingPrivate Parking
  • Free parkingFree parking
  • ParkingParking
ActivitiesActivities
  • Golf course (within 2 miles)Golf course (within 2 miles)
  • FishingFishing
  • BeachBeach
  • Tennis equipmentTennis equipment
  • Tennis courtTennis court
  • BeachfrontBeachfront
GeneralGeneral
  • HeatingHeating
  • Smoke-free propertySmoke-free property
  • Air conditioningAir conditioning
  • Designated smoking areaDesignated smoking area
  • Non-smoking roomsNon-smoking rooms
  • Family roomsFamily rooms
Guest ServicesGuest Services
  • Daily housekeepingDaily housekeeping
  • LaundryLaundry
  • Vending machine (drinks)Vending machine (drinks)
  • Shared lounge/TV areaShared lounge/TV area
InternetInternet
  • InternetInternet
  • WifiWifi
  • Free WifiFree Wifi
OutdoorsOutdoors
  • Outdoor pool (seasonal)Outdoor pool (seasonal)
  • TerraceTerrace
  • Sun deckSun deck
  • GardenGarden
SpaSpa
  • Heated poolHeated pool
  • Swimming poolSwimming pool
  • Fenced poolFenced pool

Policies

Check-in
Check-in
The minimum age for check-in is 21
Cancellation policy
Cancellation policy
Non refundable
Pet Policy
Pet Policy
Pets are not allowed
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.

Reviews

Value for money:
8.15
Location:
9.23
Staff:
8.75
Facilities:
8.56
Comfort:
8.64
Cleanliness:
8.52
David
Apr 22, 2026 07:00:00 AM
Review Score:   8
USA
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
See All Reviews

Room Arrangement

Room InfoFacilities
West Two Bedroom Suite
Room Type: Apartment
Room Size: 57 m2
2 Twin bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
West Two Bedroom Suite

Media & Technology

Telephone, Flat-screen TV, Satellite channels, Cable channels

General

Heating, Fan, Air conditioning, Trash cans, Private entrance, Iron, Hypoallergenic, Tile/Marble floor

Bathroom

Body soap, Shampoo, Conditioner, Private bathroom, Hairdryer, Toilet, Toilet paper, Towels, Bathtub or shower

Outdoors

Outdoor dining area, Terrace, Balcony, Outdoor furniture

Kitchen

Coffee machine, Kitchen, Microwave, Dryer, Stovetop, Oven, Refrigerator, Dishwasher, Kitchenware, Toaster

Living Area

Dining area, Sitting area, Sofa

Bedroom

Linens, Alarm clock, Walk-in closet

Services

Wake-up service

View

Garden view

Accessibility

Upper floors accessible by stairs only

Room amenities

Sofa bed, Non-feather pillow, Hypoallergenic pillow, Feather pillow, Clothes rack, Drying rack for clothing, Socket near the bed

Pool and Spa

Heated pool, Pool towels, Shallow end
Studio
Room Type: Studio
Room Size: 34 m2
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio

Media & Technology

Telephone, Flat-screen TV, Satellite channels, Cable channels

General

Heating, Fan, Air conditioning, Trash cans, Private entrance, Iron, Hypoallergenic, Carpeted, Tile/Marble floor

Bathroom

Body soap, Shampoo, Conditioner, Private bathroom, Hairdryer, Toilet, Toilet paper, Towels, Bathtub or shower

Kitchen

Coffee machine, Kitchen, Microwave, Dryer, Stovetop, Oven, Refrigerator, Dishwasher, Kitchenware, Toaster

Living Area

Dining area, Sitting area, Sofa

Outdoors

Patio, Outdoor dining area, Outdoor furniture

Bedroom

Linens, Wardrobe or closet, Alarm clock, Walk-in closet

Services

Wake-up service

View

Garden view

Room amenities

Sofa bed, Non-feather pillow, Hypoallergenic pillow, Feather pillow, Clothes rack, Drying rack for clothing, Socket near the bed

Pool and Spa

Heated pool, Pool towels, Shallow end
Deluxe Studio
Room Type: Studio
Room Size: 34 m2
1 Sofa bed Bed
1 Queen bed(s) Bed
Deluxe Studio

Media & Technology

Telephone, Flat-screen TV, Satellite channels, Cable channels

General

Heating, Fan, Air conditioning, Trash cans, Private entrance, Iron, Hypoallergenic, Tile/Marble floor

Bathroom

Body soap, Shampoo, Conditioner, Private bathroom, Hairdryer, Toilet, Toilet paper, Towels, Bathtub or shower

Kitchen

Coffee machine, Kitchen, Microwave, Dryer, Stovetop, Oven, Dining table, Refrigerator, Dishwasher, Kitchenware, Toaster

Living Area

Dining area, Sitting area, Sofa

Outdoors

Patio, Outdoor dining area, Outdoor furniture

Bedroom

Linens, Wardrobe or closet, Alarm clock, Walk-in closet

Services

Wake-up service

View

Garden view

Accessibility

Entire unit located on ground floor

Room amenities

Sofa bed, Non-feather pillow, Hypoallergenic pillow, Feather pillow, Clothes rack, Drying rack for clothing, Socket near the bed

Pool and Spa

Heated pool, Pool towels, Shallow end
Deluxe Two-Bedroom Apartment
Room Type: Apartment
Room Size: 57 m2
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Deluxe Two-Bedroom Apartment

Media & Technology

Telephone, Flat-screen TV, Satellite channels, Cable channels

General

Heating, Fan, Air conditioning, Trash cans, Private entrance, Iron, Hypoallergenic, Tile/Marble floor

Bathroom

Body soap, Shampoo, Conditioner, Additional bathroom, Private bathroom, Hairdryer, Toilet, Toilet paper, Towels, Bathtub or shower

Kitchen

Coffee machine, Kitchen, Microwave, Dryer, Stovetop, Oven, Refrigerator, Dishwasher, Kitchenware, Toaster

Living Area

Dining area, Sitting area, Sofa

Bedroom

Linens, Alarm clock, Walk-in closet

Services

Wake-up service

View

Sea view

Outdoors

Outdoor dining area, Terrace, Outdoor furniture

Accessibility

Upper floors accessible by stairs only

Room amenities

Sofa bed, Non-feather pillow, Hypoallergenic pillow, Feather pillow, Clothes rack, Drying rack for clothing, Socket near the bed

Pool and Spa

Heated pool, Pool towels, Shallow end
Apartment with Sea View
Room Type: Apartment
1 King bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Apartment with Sea View

Internet

Internet facilities

Media & Technology

Cable channels, TV

General

Air conditioning

View

Sea view
Studio
Room Type: Studio
1 King bed(s) Bed
1 Sofa bed Bed

Media & Technology

Cable channels, TV

General

Air conditioning
Two-Bedroom Apartment
Room Type: Apartment
1 Sofa bed Bed
1 Queen bed(s) Bed
2 Twin bed(s) Bed

Media & Technology

Cable channels, TV

General

Air conditioning
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed

General

Air conditioning

Media & Technology

Cable channels

View

Garden view
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
King Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed

General

Air conditioning

Media & Technology

Cable channels

View

Garden view
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed

Media & Technology

Cable channels, TV

General

Air conditioning
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Superior Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Full bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Sofa bed Bed
1 Queen bed(s) Bed
1 Queen bed(s) Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
2 Twin bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed
Two-Bedroom Apartment
Studio
Room Type: Studio
1 Sofa bed Bed
1 Queen bed(s) Bed

General

Air conditioning

Media & Technology

Cable channels
Studio
Room Type: Studio
1 Full bed(s) Bed
1 Queen bed(s) Bed

General

Air conditioning

Media & Technology

Cable channels

View

Garden view
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Queen bed(s) Bed
1 Sofa bed Bed

Internet

Internet facilities

Media & Technology

Cable channels, TV

General

Air conditioning

View

Sea view
Apartment with Sea View
Room Type: Apartment
2 Twin bed(s) Bed
1 Sofa bed Bed
1 Queen bed(s) Bed

Media & Technology

Cable channels, TV

View

Sea view
Two-Bedroom Apartment
Room Type: Apartment
1 Queen bed(s) Bed
1 Sofa bed Bed
1 Queen bed(s) Bed

Internet

Internet facilities

Media & Technology

Cable channels, TV

General

Air conditioning

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 Internet, Laundry, Designated Smoking Area, Fireplace/Heating, Guest Services, Parking, Pool, TV, View, Security/Safety, Sports/Activities, Balcony/Terrace, Entertainment, Air Conditioner, Ocean View, Oceanfront, Child Friendly With private courts and nearby facilities. PickleTrip™ offers a wide range of properties for pickleball players and travelers of all types. Our goal is to connect you with the perfect vacation rental, resort, or hotel that has a private pickleball court or nearby facilities, ensuring a fun and active stay.

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.

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US $317
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