The Colosseum at night with illuminated arches and surrounding street lights.

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Italy Accommodation: Most Popular Cities to Stay

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Our top choices for Italy hotels with winery

1. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (444 reviews)
"Stunning property with beautiful views and extremely friendly and helpful hosts."
United States
Mary Margaret
The price is ฿6,286
฿6,915 total
includes taxes & fees
4 Nov - 5 Nov
Castello Vicchiomaggio

2. Baglio Oneto dei Principi di San Lorenzo - Luxury Wine Resort

Baglio Oneto dei Principi di San Lorenzo - Luxury Wine Resort
5.0 star property
Marsala
9.2 out of 10, Wonderful, (404 reviews)
"Nice place to stay!"
Canada
Tatsiana
Baglio Oneto dei Principi di San Lorenzo - Luxury Wine Resort

3. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (234 reviews)
"The staff and experience staying at Castello Di Fonterutoli was amazing! Everyone was so kind and welcoming! Cannot wait to go back☺️"
United States
Micaela
The price is ฿6,137
฿6,902 total
includes taxes & fees
16 Nov - 17 Nov
Castello di Fonterutoli Wine Resort

4. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (250 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is ฿15,544
฿17,400 total
includes taxes & fees
4 Nov - 5 Nov
Borgo Vescine

5. Relais Santa Anastasia

Relais Santa Anastasia
5.0 star property
Castelbuono
9.2 out of 10, Wonderful, (261 reviews)
"Absolutely stunning property, the photos do not do it justice! The food is some of the best we’ve had in Sicily. The Veal cheeks, Guinea hen and Octopus salad were fantastic. Pool, hiking trails, staff and overall serene atmosphere will not be forgotten."
United States
Lisa
The price is ฿4,876
฿5,364 total
includes taxes & fees
28 Nov - 29 Nov
Relais Santa Anastasia

6. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (141 reviews)
"Bettina was very helpful in assisting us during our stay."
United States
William
The price is ฿8,646
฿9,661 total
includes taxes & fees
7 Nov - 8 Nov
Tenuta Santo Pietro

7. 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, (139 reviews)
"This property is pristine. Absolutely beautiful with some of the best views in Tuscany. I would recommend this experience to anyone."
United States
Jeanine
The price is ฿45,576
฿50,511 total
includes taxes & fees
7 Nov - 8 Nov
Castello Banfi - Il Borgo - Relais et Chateaux

8. Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (362 reviews)
"Beautiful property! Very clean!"
Canada
Steve
The price is ฿6,791
฿7,621 total
includes taxes & fees
26 Nov - 27 Nov
Relais Villa Grazianella - UNA Esperienze

9. Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (209 reviews)
"This was just spectacular and I cannot recommend it enough!!!"
United States
alexander
Locanda le Piazze

10. Wine Relais Feudi del Pisciotto

Wine Relais Feudi del Pisciotto
Niscemi
9.8 out of 10, Exceptional, (109 reviews)
"The hotel is beautifully restored. Too bad we only stayed 1 night , it would have been nice to stay another day and chill out in the pool. We enjoyed an aperitivo on the rooftop and the sunset was gorgeous. The staff we very nice and showed us the whole place . Conchita in the restaurant was very nice and Omma and the front desk Valerie and the rest of the staff were all nice."
United States
Jacqueline
The price is ฿6,023
฿6,625 total
includes taxes & fees
4 Nov - 5 Nov
Wine Relais Feudi del Pisciotto
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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