Discover the Pure Caribbean

retreat to Roatan's east end

Welcome To

Windward Cottages

two distinctive Roatan vacation homes

Windward Cottages are a pair of unique vacation rental properties located on the secluded East end of Roatan in the Bay Islands of Honduras — Bentley’s Hill Plantation in Helene (Santa Elena) & Caulfield’s Cottage in Camp Bay.

Yes, our lodgings are certainly comfortable and well-appointed. Yet you’ll discover they’re much more than simply another option for accommodations on the island.

Windward Cottages are an experience.

Because the settings for these homes have been selected with intention to immerse you within the wild splendour of our natural landscape, and to bring you into connection with our islands’ old and authentic way of living.

An Extraordinary experience

Trust us, this is not your typical Caribbean vacation. It’s not even your typical Roatan vacation.

Windward Cottages invites you to an insiders’ view of our island — to places where you’ll discover some of Roatan’s most breathtaking scenery, the richness of island culture, and countless opportunities for adventure.

windward cottages

A stay at Bentley’s Hill Plantation is a Caribbean vacation experience assuredly unto itself.

Nestled in a forest clearing atop a hill overlooking Bentley Bay on Helene — Roatan’s furthermost terrain to the east — the setting for this inviting one-bedroom cottage can only be described as idyllic.

Truly remote and enveloped in the sights and sounds of nature, you’ll be beckoned to explore the virtually-untouched landscape (above and below the surface of the Caribbean Sea), and find yourself drawn into the seductive simplicity of true island living … of course not forsaking a few modern comforts such as Wi-Fi and high-quality linens.

“The islands possess a more pure & exquisite beauty in the places few are fortunate to see.

— Windward Cottages

windward cottages

Built around a freshwater dipping pool and fringed by the natural foliage behind Camp Bay’s postcard-worthy beach, Caulfield’s Cottage is a lovely two-bedroom pod-style retreat. 

You’ll find yourself just steps from where powdery white sand meets sparkling aquamarine surf, relishing dreamy days spent under the shade of gently swaying coconut trees and in the waters of the Caribbean Sea. 

The essence of adventure takes the form of hiking, scuba diving, and kitesurfing, while the essence of local culture is found in a warm island community — all in convenient proximity.

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.


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


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. 


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.