Search Winery Hotels in Province of Siena

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Check availability on Province of Siena Winery Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Province of Siena hotels with winery

Breakfast, lunch, dinner served; Italian cuisine, garden views
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (201)
"Amazing experience all around! Stayed for 2 nights!"
Canada
Matthew
The price is ฿6,066
฿6,822 total
includes taxes & fees
1 Jan - 2 Jan 2026
Castello di Fonterutoli Wine Resort
2 restaurants, breakfast served
Borgo Vescine

Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (244)
"This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. "
United States
Sherie
Borgo Vescine
Exclusive Villa, 2 Bedrooms, Garden View, Annex Building | Terrace/patio
Tenuta Santo Pietro

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (119)
"Great countryside stay"
Canada
Josh
Tenuta Santo Pietro
2 restaurants, lunch, dinner served; Italian cuisine
Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (126)
"The setting, scenery and hotel were 5 star plus!"
United States
Diana
Castello Banfi - Il Borgo - Relais et Chateaux
Outdoor pool, pool loungers
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (279)
"Great room and service"
United States
ALFREDO
The price is ฿8,250
฿9,221 total
includes taxes & fees
4 Jan - 5 Jan 2026
Relais Villa Grazianella - UNA Esperienze
Exterior
Locanda le Piazze

Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (183)
"Absolutely gorgeous property!"
Canada
David
Locanda le Piazze
Exterior
Hotel Villa Campomaggio

Hotel Villa Campomaggio

Hotel Villa Campomaggio
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (164)
"Amazing place, amazing people "
United States
Nitzan
Hotel Villa Campomaggio
Restaurant
Fattoria San Donato

Fattoria San Donato

Fattoria San Donato
San Gimignano
9.4 out of 10, Exceptional, (59)
"The people were so welcoming."
United States
HERBERT
Fattoria San Donato
Minibar, in-room safe, desk, laptop workspace
Hotel Leon Bianco

Hotel Leon Bianco

Hotel Leon Bianco
3.0 star property
San Gimignano City Centre
9.4 out of 10, Exceptional, (574)
"Great breakfast, clean room, great staff, and great value overall"
Canada
Brandon
The price is ฿4,476
฿5,147 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel Leon Bianco
Exterior
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
3.0 star property
San Gimignano
9.2 out of 10, Wonderful, (449)
"Just a lovely place all over"
United States
Salome
Hotel Casolare Le Terre Rosse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Province of Siena Hotel Reviews

Hotel Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
Allyson 3-night trip
Posted 1 month ago
Hotel Borgo San Luigi
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"Very nice hotel and beautiful hotel. My only complaint is that the king bed I stayed in was very lumpy - I do mean very.. otherwise great place. Good size gym. Clean. Very friendly service."
Dan 1-night trip
Posted 3 months ago
Villa Ermellina Siena, a Tribute Portfolio Hotel