The Wine Cellar Cave House

Rooms

This quirky, split-level cave house comprises two self-contained studios. Each floor has a double bedroom, living area, shower bathroom and kitchenette, with a terrace at the front. Everything faces the sea, so you can soak up the views whether indoors or out.

Inside, it’s all vaulted ceilings, arched doorways and wonky walls painted in cool white, with blue shutters to complete the Greek-island look. Interiors are thoughtfully curated, featuring a mix of antiques, such as vintage Cretan chairs and heavy wooden storage chests, alongside luxe additions like a misshapen, marbled bathroom sink.

Outside, you’ve got three south-facing terraces to choose from, with a heated whirlpool set into an alcove behind the staircase on the lower level. Sink into the daybed or prop yourself up on the cushioned wall seat, admiring the view of Oia's cubic architecture, offset by the shimmering sea below. 

Features include:

• Air conditioning
• Bluetooth sound system
• Coffee / tea making
• Fan
• Hairdryer
• Plunge pool
• Terrace/balcony
• Toiletries
• WiFi

Eating

This house is unusual for having a kitchenette on each floor. The larger one is on the lower level and has an oven, dining table for 6, Smeg fridge and wine fridge - a must-have in a former wine cellar! A simple but satisfying breakfast is delivered discreetly every morning (think pastries, fruit, yoghurt, a few savouries), and you can easily buy ingredients for dinner from the nearby mini-market. Having the option to self-cater is a real luxury in Oia, where it’s costly to eat out all the time.

That said, you will want to explore the local dining scene on occasion. And the central location of this house means that you’ve got good restaurants right outside. Some local recommendations (courtesy of the house’s owner) include Oinosart, for all-day Greek bistro fare and a buzzy atmosphere, or Fanari, where dinner comes with beautiful sunset views.

Private chefs and cookery lessons can be arranged in-house - just speak to Ioanna, your concierge.

Features include:

• Breakfast
• Chef on request
• Coffee maker
• Dinner by arrangement
• Fridge
• Hob or stove
• Kitchenette
• Oven
• Restaurants nearby
• Toaster

Activities

• Step outside and you’re in Oia, the village you see on all the postcards, where blue-domed chapels, sugar-cube houses and chic cafes have panoramic sea views, and the sunsets are to die for
• Follow the steep but scenic footpath from the house down to Armeni Bay, where there is a restaurant, a dive centre and good swimming from the rocks
• If you want to escape the crowds, Koloumbos beach is quiet and undiscovered. It’s a 10-minute drive by car or transfer, but bring everything you’ll need as there are no umbrellas, loungers or eateries - part of the charm!
• Book a cruise - the owners have a 15m wooden yacht, or you can join a group trip - to the lava islands and around the caldera, or further afield (overnight is also possible)
• Explore the ancient sites of Thira (knee-high ruins atop a spectacular hill) or Akrotiri, a Minoan city devastated by eruptions around 1600 BC, but subsequently preserved by volcanic ash
• If you’re here for the wine, Santorini has some swish vineyards offering tastings - ask your concierge to arrange

Activities on site or nearby include:

• Boat trips
• Historical sites
• Shopping / markets
• Swimming
• Wine tasting

Kids

With lots of private space and the option to self-cater, this house is good for families. But we’d say it works best for those with older kids, as the two bedrooms are separated via an external staircase. It makes a great base if you want to see Santorini without the hassle of hiring a car, as it’s right in the island’s most famous village, with bars, shops and restaurants all walkable.

Best for:

Babies (0-1 years), Children (4-12 years), Teens (over 12)

Family friendly accommodation:

Each floor is self-contained, with a bedroom, kitchenette, bathroom and living area. Both beds are doubles, but there are sofabeds in the living areas, meaning three can sleep on each floor.

Cots Available

For more family-friendly places, see our Kids Collection

Location

The Wine Cellar Cave House is in Oia, on the northern tip of Santorini, with wonderful views across to the caldera.

By Air
Fly to Santorini (direct flights from various European cities), and take a taxi from the airport (17km) - or hire a car if you want to explore the island.

By Ferry
Santorini has daily ferry connections to its Cycladic neighbours (Folegandros, Naxos, Paros etc), as well as to Piraeus (the main port of Athens) and, in summer, to Heraklion (Crete). It's a spectacular way to arrive, but we advise leaving at least a day before your return flight, in case of ferry disruption.

On the island
You won't necessarily need a car: the island is small and traffic can clog up the roads in high season. Taxis work well if you're not planning to roam much. Note that the centre of Oia is pedestrianised.