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

This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

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, (419 reviews)
"Incredible stay."
United States
Shane
The price is ฿5,828
฿6,411 total
includes taxes & fees
29 Sept - 30 Sept
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, (225 reviews)
"Very peaceful and staff was very helpful with reservations for excursions"
United States
Giancarlo
The price is ฿7,815
฿8,750 total
includes taxes & fees
2 Sept - 3 Sept
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, (242 reviews)
"Had an amazing time. Rooms can be a bit hot at times but everything else was spectacular. Highly recommended"
United States
Gabrielle
The price is ฿30,129
฿33,449 total
includes taxes & fees
7 Sept - 8 Sept
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, (129 reviews)
"Such a wonderful stay. The view is breathtaking and Bertina and her team delightful. Our favorite place in Tuscany."
Canada
Annie
The price is ฿9,415
฿10,510 total
includes taxes & fees
30 Sept - 1 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, (131 reviews)
"Location, Service and Ambiance amazing. Truly charming location and hotel Staff were wonderful."
United States
Jason
The price is ฿51,610
฿57,154 total
includes taxes & fees
1 Sept - 2 Sept
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, (337 reviews)
"Was a wonderful stay with beautiful views in a very nice location. Definitely recommend staying here."
United States
Alisa
The price is ฿11,185
฿12,457 total
includes taxes & fees
20 Sept - 21 Sept
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, (200 reviews)
"Loved this hotel ! Staff was top notch"
United States
Mark
The price is ฿12,554
฿14,039 total
includes taxes & fees
15 Sept - 16 Sept
Locanda le Piazze

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, (181 reviews)
"This property is amazing! The views are absolutely breathtaking, and the food is delicious. I highly recommend it. It’s also a fantastic choice for families, as the staff are incredibly accommodating and welcoming toward children."
United States
Stacey
The price is ฿8,160
฿9,206 total
includes taxes & fees
28 Sept - 29 Sept
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, (63 reviews)
"Incredible property! You feel like you’re in the middle of a Tuscan fairytale! "
United States
Terranova
The price is ฿5,338
฿6,063 total
includes taxes & fees
30 Sept - 1 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 Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"Great location! Beautiful rooftop view!"
Merilyn Rodas 4-night trip
Posted less than an hour ago
The Social Hub Florence Lavagnini