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

Search Winery Hotels in Province of Siena

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Check availability on Province of Siena Winery Hotels

This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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, (231 reviews)
"Excellent stay, great breakfast and helpful staff."
India
Saion
The price is ฿6,445
฿7,240 total
includes taxes & fees
8 Nov - 9 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, (247 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is ฿15,727
฿17,601 total
includes taxes & fees
4 Nov - 5 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, (134 reviews)
"Gorgeous location with spectacular views and yummy food with very friendly and helpful staff"
United States
Robert
The price is ฿7,771
฿8,699 total
includes taxes & fees
7 Nov - 8 Nov
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 ฿37,346
฿41,458 total
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, (354 reviews)
"Was a wonderful stay with beautiful views in a very nice location. Definitely recommend staying here."
United States
Alisa
The price is ฿7,216
฿8,088 total
includes taxes & fees
5 Nov - 6 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 ฿12,335
฿13,794 total
includes taxes & fees
16 Oct - 17 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, (189 reviews)
"Great hotel"
United States
Dario
The price is ฿5,551
฿6,332 total
includes taxes & fees
3 Nov - 4 Nov
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 ฿4,883
฿5,560 total
includes taxes & fees
2 Nov - 3 Nov
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, (613 reviews)
"Very friendly and supportive staff and excellent location in the heart of the historic center."
United States
CINTHIA ELAINE DE
The price is ฿3,639
฿4,229 total
includes taxes & fees
2 Nov - 3 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, (496 reviews)
"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."
Canada
Jodie
The price is ฿5,756
฿6,558 total
includes taxes & fees
24 Oct - 25 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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"
Lauren 1-night trip
Posted 1 day ago
Fattoria di Vegi