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

Italy Winery Hotels from CA $223

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Ancient ruins with columns and a large dome structure.
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Rome

Rome

Check availability on Italy Winery Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Italy 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, (444 reviews)
"Stunning property with beautiful views and extremely friendly and helpful hosts."
United States
Mary Margaret
The price is CA $230
CA $253 total
includes taxes & fees
Oct 31 - Nov 1
Castello Vicchiomaggio
An outdoor dining area with tables and chairs under umbrellas, surrounded by greenery and palm trees.

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
9.4 out of 10, Exceptional, (403 reviews)
"Nice place to stay!"
Canada
Tatsiana
The price is CA $576
CA $644 total
includes taxes & fees
Oct 31 - Nov 1
Baglio Oneto dei Principi di San Lorenzo - Luxury Wine Resort
A narrow stone pathway leading to a rustic building with a wooden door and a window.

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 CA $236
CA $266 total
includes taxes & fees
Nov 17 - Nov 18
Castello di Fonterutoli Wine Resort
A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

4. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (249 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is CA $598
CA $671 total
includes taxes & fees
Nov 10 - Nov 11
Borgo Vescine
A cozy, rustic interior with stone arches, a central seating area with a table and chairs, and hanging plants.

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 CA $202
CA $223 total
includes taxes & fees
Nov 21 - Nov 22
Relais Santa Anastasia
A cozy room with a fireplace, two armchairs, and a table.

6. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (140 reviews)
"Bettina was very helpful in assisting us during our stay."
United States
William
The price is CA $333
CA $373 total
includes taxes & fees
Nov 7 - Nov 8
Tenuta Santo Pietro
A stone wall with a view of rolling hills and mountains.

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 CA $1,504
CA $1,670 total
includes taxes & fees
Oct 31 - Nov 1
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.

8. Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (360 reviews)
"Absolutely beautiful! Astonishing views! If you are looking for peace and quiet with great service this is the place."
United States
Maribel
The price is CA $282
CA $316 total
includes taxes & fees
Nov 26 - Nov 27
Relais Villa Grazianella - UNA Esperienze
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

9. Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (208 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 CA $567
CA $634 total
includes taxes & fees
Oct 31 - Nov 1
Locanda le Piazze
An interior with arched ceilings, a reflective floor, and stone walls.

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 CA $237
CA $261 total
includes taxes & fees
Nov 2 - Nov 3
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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Top Italy Hotel Reviews

Ruby Giulia Hotel Rome

Ruby Giulia Hotel Rome

10/10 Excellent
"Awesome location"
Theodore 1-night trip
Posted 5 hours ago
Ruby Giulia Hotel Rome

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