In the medieval city of Siena, travelers can taste delectable cuisine, marvel at stunning gothic buildings, and watch the historic biannual horse race known as Il Palio. After a full day of sightseeing, tourists will want to stay in a hotel offering comfy beds, charming interiors, and a convenient location. Boutique properties often offer this and more, as smaller properties may be short on features but big on personal service and a familial environment. Check out our picks for the best boutique hotels in Siena and start planning your getaway!

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1

Aia Mattonata Relais

Siena, Province of Siena

This small renovated farmhouse property within the rolling green hills of Tuscany oozes relaxation and romance. With only five classically rustic rooms and an adults-only policy, the upscale Aia Mattonata Relais' intimate vibe is ideal for couples seeking a secluded starting point to explore Siena and other nearby areas of Tuscany. The ultra-boutique B&B may be quaint, but with a wellness center with Turkish bath and body treatments, a saltwater infinity pool, and small exercise room, it is not lacking on features. Since it's a few miles outside of town, guests will either need to have their own car or rely on public transportation. The attentive owners aim to do what they can to accommodate guests.

2

Castello delle Quattro Torra

Siena, Province of Siena

Staying in a castle is an undoubtedly romantic experience, and the Castello Delle Quattro Torra is an affordable and familial alternative to many of the more opulent castle hotels found in the Italian countryside. A short drive from Siena, this family-run bed and breakfast has only three rooms, including an apartment and a two-story tower room, all of which can be rented by the night or -- for a discount -- by the week. There's little to do in the surrounding area, and guests really need a car, although those who love walking can hike to Siena in about 45 minutes.

3

Hotel Santa Caterina

Siena, Province of Siena

Housed in a restored 18th-century villa just outside Siena's medieval city walls, the 22-room Hotel Santa Caterina is an intimate, welcoming, mid-range little hotel, often with budget-friendly rates. It's simple and with few amenities, and guests seem to like it that way; the historic building feels authentic and atmospheric, without being chintzy or overwrought. The hotel is typically Tuscan, with antique wooden wardrobes, terra-cotta floors, and views over the picturesque countryside. An extensive, free homemade breakfast is served in the conservatory in winter, and in the lush private garden in warmer months. While there's no full restaurant, there is a small lobby bar, and room service is available 24 hours a day. In-room massages can be arranged, as can babysitting and airport transfers, and the staff offers extensive concierge service. All of Siena's main sights are within walking distance.

4

Palazzo di Valli

Siena, Province of Siena

The Palazzo di Valli is a quiet, mid-range countryside hotel on the outskirts of Siena. Housed in an old villa, this 11-room property features individually decorated, classically styled rooms with air-conditioning, free Wi-Fi, and up-to-date bathrooms. There's also a large terrace and a garden area, and breakfast, included in the room rate, is served daily. The hotel has no restaurant, but there's plenty of good eating choices in town, which is within a 10-minute walk or 20-minute drive from the hotel.