Unique Caribbean Vacation Homes, Windward Cottages, Places to stay in Roatan, Bay Islands Vacation homes, Central America Nature Retreat

Roatan, Authentically

As can be expected on a Western Caribbean island, Roatan has an abundance of resorts and vacation lodging options, as well as a myriad of parks, activities, and even whole communities which cater to the interests of tourists.

Yet there are those who come seeking more than simple sightseeing and an over-polished version of our island — those with a spirit for connection and exploration.

It’s with these travellers that we have an affinity, and with whom Windward Cottages will resonate best. Because, in fact, our Roatan vacation rentals offer a completely un-curated experience within a traditional and immersive context.

So while we’ve furnished our accommodations with amenities you’ll appreciate and have services available for your convenience and delight, our real gift to you is the opportunity to encounter our island in a genuine and meaningful way.

We invite you to come experience the true essence of Roatan.

Inviting you to a rare & unforgettable island experience

at Windward Cottages

Caribbean Nature Retreat, Helene Roatan, Santa Elena Honduras, Bentley's Hill Plantation, Windward Cottages
Roatan Culture, Roatan History, Bentley Bay
Bentley Bay - 1986
Helene Village Yard - 1986
Matthew Harper - late 1980's
Matthew Harper - today
Matthew Harper's Book
Matthew Harper at Helene energy inauguration - 2019

“My wish is that you'll become truly immersed in the alluring landscape, culture & history of Roatan.

— Matthew Harper, Windward Cottages

over 35 years on roatan

My Story

I came to the Bay Islands in my early twenties when the island was a dreamy little desert island.  Everyone knew everyone else and Spanish was hardly heard spoken.

I ‘grew up’ on the island in Helene and Oakridge (prior to the development boom) when the only jobs going were associated with commercial fishing, welding, diving, carpentry and lots of other interesting activities.

With the boom came a certain level of prosperity and I made a name for myself, forging a career in the energy industry. I served in many positions from being a meter reader in the early days to Director of Operations in the latter years. I am proud to have been a part of designing and building some of the most cutting-edge facilities in the Caribbean — my proudest being the 4 km subsea power line to St.Helene, completed in 2019.

I’m back in the private sector now doing much of the same, but my passion is writing and the enjoyment of my properties in the still-very-Caribbean windward side of Roatan (or “Rattan” as I prefer to call it in honour of the first British settlers here).

matthew harper

My Book

A collection of short stories, 'A Handful of Seashells' includes several narratives from my experiences on Roatan's East End. A copy of the book is provided at each of the Windward Cottages, and I hope the anecdotes it contains will add to your enjoyment while you find yourself within the scenery they describe. If you wish to have a copy of your own, my book is available for purchase from Amazon.

See my book on Amazon

My Roatan History Blog

As one fascinated by history, particularly that of the British influence on the Bay Islands, my blog is largely dedicated to relating facts and accounts I've gathered about some of the compelling figures and events from our islands' past.

Visit my blog

Reach Out

If you have any questions or requests, please don’t hesitate to let us know. We’re happy to help you however we can. 

Windward Cottages

Availability

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Bentley's (Helene)
Caulfield's (Camp Bay)
See Bentley's Hill Plantation
See Caulfield's Cottage

[email protected]

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Windward Cottages

House Rules

Check In / Out

Check-in on your arrival date is from 3pm. 

Checkout on your departure date is by 11am.

General Respect

As a general rule, we ask that your conduct while on the property and in the neighborhood is one of respect (for your hosts, for neighbors, and for the property).

Occupancy & Visitors

Maximum occupancy at Bentley’s Hill Plantation is 2 guests; 5 guests maximum at Caulfield’s Cottage.

Visitors who are not on the reservation are not permitted on the property without prior authorization.

Pets

We do not accept pets at our properties. Registered service animals with proper documentation are permitted; owners are expected to keep the grounds free from waste.

Additional Rules

– No glass in or near the pool (Caulfield’s Cottage).
– No events or loud partying.
– No drugs of any kind are permitted on the premises.
– Smoking cigarettes is not allowed indoors or on the decks. Smoking is permitted outdoors provided that cigarettes are outed completely and butts are properly disposed of and removed. A $500 cleaning fee will apply for smoking indoors.

Please Note

Our septic systems can process toilet paper and human waste only; a $250 fee will apply for plumbing issues resulting from flushing wipes, sanitary products, or other items.

Fees will also apply in the event of damage to the property, missing items, or the requirement of cleaning above what is standard for a typical checkout. 

Windward Cottages

Booking Policies

Reservations

A 50% deposit is required within 24 hours of receiving the payment link in order to confirm a reservation. The full balance is due 30 days prior to arrival (a link will be sent 5-7 days in advance of the due date). For reservations made 30 days or fewer prior to arrival, payment is due in full within 24 hours of receiving the link. 

Cancellations

Reservations cancelled 60 days or more prior to arrival are fully refundable, minus the cost of 1 night at the seasonal nightly rate. Cancellations 31-59 days in advance are entitled to a 50% refund of the deposit paid.  Cancellations 30 days or fewer prior to arrival are non-refundable. For reservations paid with partial deposit, if the balance is unpaid by the due date, the reservation will be considered cancelled, and the full deposit forfeit.