Places to Stay
Stays I'd send friends to
Villas, guest houses, apartments and hotels — every listing comes with my honest tip.
Sea-view hillside villa
📍 Olveston
Private pool, garden fruit trees and sunsets over the Caribbean Sea. Sleeps 6.
My tip: ask for the upstairs bedroom — you’ll wake up to Redonda on the horizon.
Sleeps 6
Garden guest house
📍 Woodlands
Family-run, five minutes’ walk from Woodlands Beach, breakfast included.
My tip: the hosts make the best banana bread on island. Say yes.
Breakfast incl.
Boutique bay hotel
📍 Little Bay
Steps from the water in the island’s new capital-to-be. Restaurant on site.
My tip: book a sea-facing room for the Friday night music drifting up from the beach bars.
Restaurant on site
Bayside apartment
📍 Salem
Self-catering one-bed with a veranda made for morning coffee and sea views.
My tip: the Saturday market is a ten-minute walk — go early for the good mangoes.
Self-catering
Ridge-top retreat
📍 Woodlands
Three bedrooms above the treetops, plunge pool, and the best sunset deck I know.
My tip: birdwatchers: orioles visit the garden most mornings.
Sleeps 8
Heritage creole cottage
📍 Cudjoe Head
A lovingly kept traditional cottage — gingerbread trim, big veranda, bigger welcome.
My tip: ask for the veranda rocking chairs at golden hour.
Sleeps 2
Run a villa, guest house or hotel on Montserrat?
Featured listings and partnerships are coming — get in early.
Before you book
Quick advice
Book early for March
St Patrick’s Festival fills the island — stays go months ahead.
Consider a car
Most stays are on hillsides — a rental makes beaches and dinners easy.
North is home base
All accommodation sits in the safe, green north of the island.
Ask about minimums
Some villas prefer 3+ night stays, especially in high season.