Chilean Wine Valleys to Valparaíso
How comfortable?
Really very comfortable but always with an eye on character and style. Overall, expect 4* type levels of comfort. We avoid chain hotels in favour of owner-hosted properties which get you closer to the places you are visiting.
Hotel Magnolia is a beautifully modern restoration of a classic building in the heart of Santiago. Location-wise you are steps away from the park of Santa Lucía Hill, the riverside park and fine arts museum and from the restaurants and wine bars of the Lastarrria neighbourhood. The rooms themselves are very comfortable, spacious and clean. There's a bar and decent restaurant downstairs if you want to just rest up after a long journey. 
Casa Bouchon is a 5-room boutique hotel which sits within a 150-year-old traditional adobe hacienda, which itself sits within a sprawling wine estate in the dry plains of the Maule Valley. This is very much a working winery, with views stretching off to the low mountains of the coastal range. Rooms are simply decorated in the local style, lots of white and texture and natural materials. There's not a telly in sight.

Importantly, there is a hot tub fashioned out of a large oak foudre barrel that once stored the estate's wine. This looks out across a small swimming pool. You have dinners included in your stay here, delicious Chilean homecooking based around seasonal and local produce. There's also an honesty bar that lets you help yourself to drinks and snacks whenever the mood takes you.
Billed as a 'gastronomy hotel', Mapuyampay Lodge is a place for food, wine and nature lovers. The estate is nestled in the foothills of the Andes, in the heart of the Chilean winelands. There are just five rooms, individually decorated and all wonderfully quiet and comfortable.

The lodge is owned and run by the lovely Ruth (the foodie) and Yampay (the wine buff), they and their team will absolutely make you feel at home during your time here. The garden is particularly beautiful in spring and is alive with small birds flitting to and fro - hummingbirds are among the 40+ species spotted on the grounds.
Hotel TerraVina is a lovely boutique hotel surrounded by four hectares of vines. It's very much the passion project of your hosts Anne & Eduardo which gives it the friendly atmosphere which people enjoy so much. As well as the restaurant on site, you are within walking distance of the town - as well as other small wineries. Your hosts will help you arrange your time here if you want. But it's also a place to simply kick back and relax, enjoy some warm sunshine, a dip in the pool and a glass of Chile's finest. 
The Hotel Casadoca is located on the coast, 20 minutes from Viñas del Mar and 30 minutes from Valparaíso. With just nine rooms it's nice and small, but with big views out of the window to the Pacific Ocean from five of them. For us, it's the perfect way to see the city but then retreat to somewhere peaceful at the end of the day. If you want to stay put, there's a good restaurant with a constantly changing menu on site and as a nice bonus there's also a small spa with saunas and a Jacuzzi.