What are your check-in and check-out times?

Rooms are guaranteed to be ready by 4:00 pm.   There is no “early check-ins” available.  If you arrive before your room is ready, you are welcome to use the facilities (eg. beach chairs, private outside showers, outdoor picnic area and BBQ grills).

Check-out is at 11:00 am.  We do not have “late check-outs” available.   Once checked out of your room, you are welcome to hold your beach badges and use the outdoor showers until 5:00 pm without an additional fee.

Do you allow pets?

Sorry no pets allowed.  Guests in violation of this will incur a minimum of $250 cleaning fee.

What is the age limit to rent a room at the Windward?

You must be at least 25 years old to reserve a room.

What is your Booking and Cancellation Policy?

One night stays require payment in full and are non-refundable.
For stays of two nights or more, a deposit of 50% is required at booking.
The balance is due 14 days prior to arrival.

  • Cancellations 30 days or more prior to arrival will be refunded less an $80 booking fee, for each room on the reservation.
  • Cancellations within 30 days of arrival will forfeit deposit.
  • Cancellations within 14 days of arrival will forfeit total amount paid.

Due to our small size, cancellations affect us significantly and leave us little time to refill the space you have left.

** SPECIALS, DISCOUNTS and THIRD PARTY bookings (Booking.com, Priceline, Kayak, etc.) require payment in full and are non-refundable.

Is parking available?

We have two parking spots on Amber Street side for unloading/loading purposes only.   Street parking is available.  Most guests find a spot right in front.   The great thing about the Windward is that once you park, you are walkable to all the restaurants, supermarket, pharmacy, ice cream, bagel store and bay village.  Street parking has no time limitations and no fees.

Do you have a coffee pot in the room?

No, but we have Keurig coffee in the lobby coffee bar 24/7.

Is there an elevator?

No, we are a Victorian house with 3 floors.  Rooms 10 and 11 are on the 3rd floor with steep “Victorian” stairs leading from the 2nd to the 3rd floor.   If accessibility is a concern, please book a room on the first floor.

What are the quiet hours at Windward?

The Windward quiet hours are from 10pm to 8am.  Please be courteous of others.

How do beach badges work?

Beach badges are provided on loan to guests (ages 13 and older) at no additional cost.  Beach badges must be returned to us by 5pm on day of checkout or there would be a $40 charge per badge if badges are lost or not returned.

Please note: Beach badges will be provided to registered guests starting the last Saturday in June until Labor Day.

Do you provide laundry facilities?

We do not provide laundry facilities on site for guest use.

Is Wi-Fi available?

We do provide Wi-Fi at no charge to our guests.  It is through Xfinity.

Is smoking allowed?

We are a NON-SMOKING property including porches and outdoor spaces.  Smoking in the room, porches, and outdoor patios will incur a minimum charge of $250 to clean and detox the area.

Do you have cots and cribs available?

Cots, cribs and pack and plays are not available at the Windward.

Is there a spot to leave bicycles?

We have a bike rack out front.   Please bring a lock for your bikes.

Is the Windward oceanfront?

We are 60 steps from the Atlantic Ocean.

Are there BBQ grills available for cooking on the property?

Yes, there are two BBQ grills on the property – one on the front patio area and the other in the back patio.  Picnic tables and chairs are also available for guest use.

Is there an ice machine on the property?

Yes, there is an ice machine located next to the office on the first floor to fill room ice buckets or cups.