A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

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Tuscany Accommodation: Most Popular Cities to Stay

A cityscape with prominent historical architecture, including a large dome and a bell tower.
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Florence

Florence
The Leaning Tower of Pisa with tourists in the foreground.
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Pisa

Pisa

Check availability on Tuscany Winery Hotels

Our top choices for Tuscany hotels with winery

A pool with a view of a lush valley and distant buildings.

1. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (441 reviews)
"Stunning property with beautiful views and extremely friendly and helpful hosts."
United States
Mary Margaret
The price is ฿6,267
฿6,894 total
includes taxes & fees
2 Nov - 3 Nov
Castello Vicchiomaggio
A narrow stone pathway leading to a rustic building with a wooden door and a window.

2. 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 ฿5,323
฿6,005 total
includes taxes & fees
18 Oct - 19 Oct
Castello di Fonterutoli Wine Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

3. 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 ฿15,497
฿17,347 total
includes taxes & fees
20 Oct - 21 Oct
Borgo Vescine
A cozy room with a fireplace, two armchairs, and a table.

4. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (136 reviews)
"Gorgeous location with spectacular views and yummy food with very friendly and helpful staff"
United States
Robert
The price is ฿8,609
฿9,621 total
includes taxes & fees
22 Oct - 23 Oct
Tenuta Santo Pietro
A stone wall with a view of rolling hills and mountains.

5. 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 ฿37,240
฿41,339 total
includes taxes & fees
30 Oct - 31 Oct
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.

6. 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 ฿7,195
฿8,065 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.

7. 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 ฿12,299
฿13,755 total
includes taxes & fees
26 Oct - 27 Oct
Locanda le Piazze
Outdoor pool

8. Villa Loggio Winery and Boutique Hotel

Villa Loggio Winery and Boutique Hotel
Cortona
10.0 out of 10, Exceptional, (3 reviews)
"Staff was amazing. "
Canada
Chloe
Villa Loggio Winery and Boutique Hotel
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

9. 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 ฿5,535
฿6,314 total
includes taxes & fees
3 Nov - 4 Nov
Hotel Villa Campomaggio
A narrow street with stone buildings, wooden barrels, and potted plants.

10. 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 ฿4,869
฿5,544 total
includes taxes & fees
20 Oct - 21 Oct
Fattoria San Donato
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 Tuscany Hotel Reviews

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"The social hub is great what it offers. The staff is super helpful and is very modern and clean compared to other lodging options in Florence."
Chris 2-night trip
Posted less than an hour ago
The Social Hub Florence Belfiore