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Our top choices for Penna hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is AU$212
includes taxes & fees
28 Dec - 29 Dec
La Certosa di Pontignano

Antiche Mura

Antiche Mura
Arezzo Centro Storico
9.4 out of 10, Exceptional, (86)
"It was my second stay at the Antiche Mura, and I was pleased to find that it remains a very comfortable place right in the middle of the city, near the main cathedral. "
United States
Dennis
Antiche Mura

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$191
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano

Cento Passi Dal Duomo

Cento Passi Dal Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (37)
"Very well located to visit the town"
United States
Miguel
Cento Passi Dal Duomo

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is AU$214
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo di Pietrafitta Relais

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (177)
"Ideal country setting"
Canada
Dee
The price is AU$164
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Palazzo San niccolò & Spa

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (91)
"This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying."
United States
Karem
Castello di Meleto

B&B Country House Poggio del Drago

B&B Country House Poggio del Drago
Civitella in Val di Chiana
9.8 out of 10, Exceptional, (57)
"Staff were friendly and helpful. Breakfast was just right - some fresh fruit would be nice to have. B&B was clean and tidy. Good signage so place was reasonably easy to find."
United States
Ludwig
B&B Country House Poggio del Drago

La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
9.6 out of 10, Exceptional, (118)
"A beautiful location, fantastic view, close to wineries, little shops and local restaurants. "
Canada
Rob
La Pensione di Vignamaggio

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
9.2 out of 10, Wonderful, (99)
"A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia"
Canada
Ian
The price is AU$861
includes taxes & fees
5 Jan - 6 Jan 2026
Il Borro - Relais & Châteaux

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (275)
"We loved it was easy to get to wineries or small towns we wanted to visit"
United States
Carol
The price is AU$188
includes taxes & fees
6 Jan - 7 Jan 2026
Palazzo Leopoldo Dimora Storica & Spa

Agriturismo Cuprena

Agriturismo Cuprena
Arezzo
9.6 out of 10, Exceptional, (20)
"Extra friendly staff, personalized service, and a beautiful house with amazing accommodations. "
United States
Michelle
The price is AU$478
includes taxes & fees
27 Dec - 28 Dec
Agriturismo Cuprena

Albergo Villa San Michele

Albergo Villa San Michele
Greve in Chianti
10.0 out of 10, Exceptional, (4)
"Loved this isolated escape within amazing proximity to historical vineyards and gorgeous landscapes."
Italy
Michael
The price is AU$220
includes taxes & fees
2 Jan - 3 Jan 2026
Albergo Villa San Michele

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is AU$153
includes taxes & fees
26 Jan - 27 Jan 2026
Cameracaffè Centro

Hotel Chenno

Hotel Chenno
2.0 star property
Subbiano
7.8 out of 10, Good, (25)
"Gestione familiare ottima accoglienza nessun problema per i bagni esterni ottimo rapporto qualità prezzo "
Italy
pietro
The price is AU$79
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Chenno

Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
3.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (198)
"Amazing place !Food Resturant was the best including breakfast ❤️the staff will go out of there way for you and helpful with transportation if needed."
United States
Yolanda M
The price is AU$123
includes taxes & fees
11 Jan - 12 Jan 2026
Hotel Tenuta Il Burchio

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
8.6 out of 10, Excellent, (38)
"Cute secluded property l!"
United States
Courtney
The price is AU$270
includes taxes & fees
28 Dec - 29 Dec
Borgo Casa al Vento

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40)
"Lovely pool Breakfast good"
United Kingdom
christine
The price is AU$156
includes taxes & fees
18 Jan - 19 Jan 2026
Torrebianca Tuscany

Casale La Gora

Casale La Gora
Figline e Incisa Valdarno
9.6 out of 10, Exceptional, (21)
"Casale La Gora in Tuscany. The property is beautifully renovated, blending historic charm with modern architecture. Our room was clean and cozy, the breakfast was delicious, and the pool was perfect for cooling off during the hot summer days. The host was warm, friendly, and always helpful, which made our stay even more enjoyable. We would definitely love to come back! "
Sweden
Besarta
The price is AU$154
includes taxes & fees
11 Jan - 12 Jan 2026
Casale La Gora

Le Lappe

Le Lappe
Cavriglia
9.6 out of 10, Exceptional, (32)
"Beautiful property in countryside Tuscany region ideal to stay for 2-7 days."
Canada
shrirang
Le Lappe
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 Penna Hotel Reviews

Recent Reviews in Penna

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Frequently asked questions

Where is the best place to stay in Penna?
A Point Arezzo Park Hotel, located 12.4 mi (19.9 km) from the heart of Penna, is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Villa La Borghetta Resort and Hotel Continentale. See all available top hotels, or vacation rentals in Penna.
What are some of the best holiday rentals that Penna has to offer?
Borgo Argiano: This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library. See all vacation rentals in Penna.
If I need to cancel my hotel reservation in Penna, will I receive a refund?
Yes, you'll find most hotel bookings are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Penna.
What's the best dog-friendly hotel in Penna?
Break House Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Penna.
What are some hotels with pools in Penna?
A Point Arezzo Park Hotel: Features 2 restaurants, a seasonal outdoor pool and a full-service spa. Villa La Borghetta Resort and Villa Casagrande Resort & SPA are two additional hotels that feature an on-site pool. View all hotels with pools in Penna.
What's it like to stay in Penna?
Travellers to Penna will find plenty to explore and enjoy. In Penna, there are 8 hotels and other accommodation options to choose from. Find out more about Penna.
What should I do while I'm visiting Penna?
Places to visit in the wider area include Mulino Ad Acqua, Croce del Pratomagno and Fattoria La Vialla. You'll also find Badia a Coltibuono and Castello di Albola in the area. Take a look at what more there is to see and do in Expedia's Penna guide.
What's the weather like in Penna?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Penna is 902 mm.

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