A historic town with a prominent tower and a rainbow arching over it.

Search Winery Hotels in Province of Siena

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Province of Siena Accommodation: Most Popular Cities to Stay

A hillside town with historic buildings and a prominent church.
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Montepulciano

Montepulciano

Check availability on Province of Siena Winery Hotels

Our top choices for Province of Siena hotels with winery

A narrow stone pathway leading to a rustic building with a wooden door and a window.

1. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (232 reviews)
"Excellent stay, great breakfast and helpful staff."
India
Saion
The price is £145
includes taxes & fees
18 Nov - 19 Nov
Castello di Fonterutoli Wine Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

2. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (248 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is £343
includes taxes & fees
2 Nov - 3 Nov
Borgo Vescine
A cozy room with a fireplace, two armchairs, and a table.

3. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (137 reviews)
"Gorgeous location with spectacular views and yummy food with very friendly and helpful staff"
United States
Robert
The price is £193
includes taxes & fees
22 Oct - 23 Oct
Tenuta Santo Pietro
A stone wall with a view of rolling hills and mountains.

4. 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, (137 reviews)
"Location, Service and Ambiance amazing. Truly charming location and hotel Staff were wonderful."
United States
Jason
The price is £900
includes taxes & fees
1 Nov - 2 Nov
Castello Banfi - Il Borgo - Relais et Chateaux
A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

5. Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (357 reviews)
"Was a wonderful stay with beautiful views in a very nice location. Definitely recommend staying here."
United States
Alisa
The price is £165
includes taxes & fees
18 Nov - 19 Nov
Relais Villa Grazianella - UNA Esperienze
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

6. Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (207 reviews)
"This property is beautiful, our room was beautiful, and every staff member was friendly and very helpful. It is pretty centrally located - close to Siena and San Gimignano. We would stay here again!"
United States
Colleen
The price is £309
includes taxes & fees
25 Oct - 26 Oct
Locanda le Piazze
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

7. Hotel Villa Campomaggio

Hotel Villa Campomaggio
4.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (191 reviews)
"Great hotel"
United States
Dario
The price is £142
includes taxes & fees
20 Oct - 21 Oct
Hotel Villa Campomaggio
A narrow street with stone buildings, wooden barrels, and potted plants.

8. Fattoria San Donato

Fattoria San Donato
San Gimignano
9.4 out of 10, Exceptional, (64 reviews)
"Incredible property! You feel like you’re in the middle of a Tuscan fairytale! "
United States
Terranova
The price is £124
includes taxes & fees
23 Oct - 24 Oct
Fattoria San Donato
An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.

9. Hotel Leon Bianco

Hotel Leon Bianco
3.0 star property
San Gimignano City Centre
9.4 out of 10, Exceptional, (614 reviews)
"Very friendly and supportive staff and excellent location in the heart of the historic center."
United States
CINTHIA ELAINE DE
The price is £87
includes taxes & fees
3 Nov - 4 Nov
Hotel Leon Bianco
A gated entrance with tall cypress trees, a paved path leading to a building with a yellow facade, and a mountain in the background.

10. Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
3.0 star property
San Gimignano
9.2 out of 10, Wonderful, (497 reviews)
"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."
United States
jacquelyn
The price is £121
includes taxes & fees
25 Oct - 26 Oct
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 Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"It's a lovely hotel, but it is the staff that make it truly special. Attentive and cheerful, I felt well looked after from the moment I walked in. Wonderful stay, I'll definitely be back."
Doralba 2-night trip
Posted 7 hours ago
Hotel Villa Ricci

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