A luxury island hotel, fully booked — even in shoulder season.
A boutique hotel with extraordinary guest reviews and an occupancy problem.
The property is one of the most beautiful luxury hotels on Martha's Vineyard — but the business was almost entirely seasonal. Memorial Day to Labor Day was sold out at premium rates. The other nine months: 30–40% occupancy, heavy reliance on OTAs, margins compressed by commission fees.
Ownership wanted year-round revenue without diluting the brand. Most "shoulder season" plays — discounts, promo packages, OTA pushes — would have done exactly that.
Repositioned the hotel as a year-round destination, not a summer one.
We started with brand work. Reframed the property's story around what the island actually is in the off-season: quiet, cinematic, restorative — a different luxury, not a lesser one. Commissioned new photography that captured the island in October fog and February light, not just July sunshine.
Then rebuilt the booking site on a custom stack with a direct-booking incentive program designed to pull guests off OTAs. Layered in paid search and Meta with creative that targeted high-net-worth households in NYC, Boston, and DC for shoulder-season weekends. Built a Klaviyo lifecycle program for past guests with hyper-segmented offers — wine country weekends in October, writers' retreats in February, anniversary stays in March.
Year two, we leaned in: partnerships with high-end editorial, a referral program for past guests, and a pricing strategy that protected the brand while filling rooms.
Fully booked — every season.
By month 14, shoulder-season occupancy crossed 80%. Today the hotel is consistently booked 9 months out, including off-peak weekends. OTA dependence dropped from 60% of bookings to 22%.