22 Best Wine hotels in Chianti (2025)

Chianti isn’t just a wine — it’s a place, a vibe, and a scenic masterpiece. Nestled between Florence and Siena, the Chianti region rolls through hills and valleys where some of Tuscany’s best grapes (and wines) are born. Draw a squiggly line around this slice of heaven and you’ve got a landscape of vineyard views, sun-soaked wheat fields, cypress-lined roads, medieval hilltop towns, and olive groves straight out of a postcard. The best wine hotels in Chianti make the most of this setting, pairing epic scenery with equally epic wines — and yes, unforgettable food. Whether you’re after a castle stay, a rustic farmhouse, a villa with a view, or a restaurant with rooms (and maybe a cooking class or two), our Gurus have picked the perfect spot for every taste and budget.

For the Album

• Perched on a Tuscan hilltop, Borgo Pignano blends rustic charm with luxury — think frescoed suites, vineyard terraces, an infinity pool, and 750 acres of dreamy views. Stay in the villa or cosy cottages, and enjoy art, yoga, cinema nights, and more in this countryside escape made for indulgence.

For the Views

• Set atop a hill surrounded by its own vineyards, Relais Borgo san Felice, an elegant country estate, offers 33 spacious rooms, a pool, tennis, billiards, and a standout Mediterranean restaurant. Expect rustic charm with refined touches, sweeping views, and wine tastings that showcase their impressively long list of local vintages.
• Perched in the Chianti hills, Castello La Leccia charms with sweeping vineyard views, a serene spa, and a sunset-ready pool. Artisan details and soft Tuscan tones create the perfect backdrop for unwinding in style.

For Foodies

• Villa Sassolini is a dreamy hilltop hideaway for food lovers, with gourmet dining, cooking classes, and sweeping Chianti views. Its five elegant rooms blend muted tones with romantic charm. Think lavender-scented gardens, sun-drenched terraces, and a pool made for long, lazy afternoons.
• Villa Bordoni blends Tuscan warmth with a hint of the Med — think blue walls, palm trees, and vineyard views. Inside, it’s all rustic elegance: terracotta floors, beamed ceilings, and canopied beds. With 11 stylish rooms, a top-notch restaurant, and a cooking school, it’s a foodie’s countryside dream.

For Romantics

• Castello di Tornano is a castle made for romance — think turret bedrooms, four-poster beds, and sunset views over olive groves and vineyards. Swim where the moat once flowed, dine by candlelight on local cuisine, or stargaze from the towers. It’s the ultimate medieval fantasy for two, with total countryside seclusion.
• Step into a storybook at Castelletto di Montebenichi, a 12th-century castle hideaway. With just nine elegant apartments, stained glass, antiques, and sweeping Chianti views, it's perfect for couples seeking quiet, history, and charm. Private terraces and hidden garden spots make it easy to get lost in the romance.
• Salvadonica is a vineyard-wrapped farmhouse made for romantic escapes. Sip wine on the terrace, stroll through olive groves, or linger over dinner as the sun dips behind the valley. With cosy-chic rooms, a dreamy pool, and frescoed walls, Salvadonica is effortlessly intimate and beautifully laid-back.
• The Club House is an adults-only haven nestled in Chianti’s hills, which is perfect for a romantic escape. Think serene pools, a world-class spa, and elegant Tuscan interiors. A luxurious blend of relaxation, gourmet dining, and breathtaking scenery awaits.

For a Rural Retreat

• Castel Monastero is a stunning 11th-century hamlet turned luxe retreat, with 61 elegant rooms set among gardens and stone cottages. Expect Gordon Ramsay dining, a chic cellar bar, spa bliss, and waterfall pools — perfect for unwinding in style after days exploring the rolling Chianti hills.
• Tucked away in Chianti’s rolling hills, Pieve Aldina is a rustic-luxe escape that offers terracotta floors, crackling fireplaces, a serene spa, and a pool with countryside views. It's pure Tuscan tranquillity with a touch of indulgence.

For Families

• Tucked among olive groves and vineyards, Hotel Le Fontanelle, a luxe hamlet-style retreat, has spacious rooms and villas perfect for families. Kids can splash in the panoramic pool while parents unwind in the spa or enjoy local flavours at the restaurant.
• Castello di Spaltenna is a storybook castle in the Chianti hills with family-sized rooms and apartments. There’s a kids’ pool, gourmet dining, vineyards to explore, and even babysitting so parents can enjoy the spa or wine cellar worry-free.
• Castello di Bibbione is a hilltop Tuscan castle offering roomy apartments and even a full farmhouse for large families. Kids love the infinity pool and garden space, while adults enjoy peaceful views and plenty of rustic charm inside and out.

For a Countryside Escape

• Villa Le Barone is a dreamy 14th-century Tuscan villa with vineyard views, antique-filled rooms, and a saltwater pool. Join wine tastings, cooking classes, and unwind in gardens that feel like a movie set.
• Stay in a medieval hamlet turned hideaway at Il Borgo di Vescine. Wind through cobbled paths, savour Chianti cuisine, ride horses, or sip wine under the stars. It's peaceful, scenic, and full of Tuscan charm — just minutes from Siena.
• Escape to a charming Tuscan estate set among rolling vineyards at Agriturismo Vignamaggio. Stay in rustic villas with beamed ceilings, terracotta floors, and antique touches. Relax by the pools, indulge in spa treatments, and savour world-class Tuscan food and wine.

For Traditional Charms

• Relais Vignale is a restored 18th-century villa turned boutique hotel with 42 charming rooms. Expect terracotta floors, beamed ceilings, and rustic antiques. Lounge by the pool, dine on the Tuscan terrace, sip wine among vineyards, then taste more at the cellar doors just beyond your doorstep.

For Great Value

• Stay in a real medieval villa at Castello di Fonterutoli, with chic interiors, a top-tier wine list, and serious character. Expect thoughtful design, great food, and historic charm at very reasonable rates in the heart of Chianti.

Best B&Bs

• Agriturismo Poggiacolle is a dreamy Tuscan farmhouse B&B near San Gimignano, with vineyards, saffron fields, and just four rustic-chic apartments. Think beamed ceilings, terracotta floors, and four-poster beds — plus shared perks like a tennis court, gardens, play area, and an infinity pool with knockout countryside views.

Still not sure?

• Browse through our suggestions for the best wine hotels in Tuscany, the best agriturismo in Tuscany, or the best Tuscan hotels for food and wine.
• Or expand your search even further to include all our recommendations in Tuscany.
• Alternatively, you could contact one of our friendly Gurus for personalised advice.