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Our top choices for Penna hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (546 reviews)
"Amazing property, loved staying there. Huge rooms, AC worked well, beautiful setting. It’s well worth your time to stay there"
United States
Ken
The price is AU$236
includes taxes & fees
29 June - 30 June
La Certosa di Pontignano

Chapter Chianti

Chapter Chianti
5.0 star property
Cavriglia
The price is AU$538
includes taxes & fees
13 July - 14 July
Chapter Chianti

Albergo San Lorenzo

Albergo San Lorenzo
3.0 star property
Poppi
8.6 out of 10, Excellent, (21 reviews)
"We had a clean room with a beautiful view of the Poppi castle and Tuscany landscape. The concierge recommended some incredible restaurants during our visit which were so good! The breakfast was basic but still good, and parking was readily available. Highly recommend! "
Canada
Brandon Vernon
The price is AU$140
includes taxes & fees
29 June - 30 June
Albergo San Lorenzo

Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
9.8 out of 10, Exceptional, (20 reviews)
"The Castello Di Montemasso is a beautiful place with nice staffs. Their breakfast is awesome."
United States
Quan
The price is AU$230
includes taxes & fees
5 July - 6 July
Castello Di Montemasso

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (97 reviews)
"This place is amazing. Wonderful drive to the hotel and the solitude is so great. The breakfast was amazing. Staff was very friendly for our stay. Definitely go back."
Canada
Shawn
The price is AU$193
includes taxes & fees
2 July - 3 July
Agriturismo San Sano

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (396 reviews)
"The hotel is beautiful."
United States
Ruth
The price is AU$312
includes taxes & fees
5 July - 6 July
Castello Vicchiomaggio

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (165 reviews)
"Our girls loved having the upstairs to themselves, the staff was friendly and helpful, and the breakfast was *delicious!*"
United States
Michelle
The price is AU$181
includes taxes & fees
5 July - 6 July
Hotel Il Viandante

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (177 reviews)
"Poor service and guidance."
United States
Cely
The price is AU$241
includes taxes & fees
23 July - 24 July
Borgo di Pietrafitta Relais

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is AU$378
includes taxes & fees
11 July - 12 July
Castello di Tornano Wine Resort

Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
3.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (206 reviews)
"Amazing experience in nature and cozy atmosphere, breakfast is super, restaurant as well. "
Netherlands
OY
The price is AU$119
includes taxes & fees
12 July - 13 July
Hotel Tenuta Il Burchio

Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (222 reviews)
"Incredible place to stay in the Chianti region. Beautiful grounds, amazing food, clean and comfortable rooms, and incredible staff. Location was perfect too! "
United States
Alex
The price is AU$116
includes taxes & fees
30 June - 1 July
Hotel Casafrassi

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (123 reviews)
"Friendly staff and walking distance to town"
United States
Scott
The price is AU$160
includes taxes & fees
30 June - 1 July
Hotel Colle Etrusco Salivolpi

Torre a Cona Wine Estate

Torre a Cona Wine Estate
Rignano sull'Arno
9.6 out of 10, Exceptional, (100 reviews)
"Everything from the welcome at the start of our stay, until the moment we checked out was fantastic. The location is breathtaking, the rooms and pool were amazing."
United Kingdom
Tom
The price is AU$573
includes taxes & fees
14 July - 15 July
Torre a Cona Wine Estate

Casa Ruffino

Casa Ruffino
Bagno a Ripoli
10.0 out of 10, Exceptional, (20 reviews)
"The best stay of my life "
United States
Oleksandr
The price is AU$444
includes taxes & fees
7 July - 8 July
Casa Ruffino

Hotel Rifugio la Foresta

Hotel Rifugio la Foresta
3.0 star property
Reggello
8.6 out of 10, Excellent, (12 reviews)
"Nice place friendly staff nice hiking areas "
United States
Gezim
The price is AU$174
includes taxes & fees
30 June - 1 July
Hotel Rifugio la Foresta

Azienda agricola la camporena

Azienda agricola la camporena
Greve in Chianti
The price is AU$235
includes taxes & fees
29 June - 30 June
Azienda agricola la camporena

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (51 reviews)
"Beautiful setting, felt like we were staying in a castle! The beds were comfortable and the property was amazing. Highly recommend this place."
Canada
Heather
The price is AU$111
includes taxes & fees
29 June - 30 June
Fondaco del Moro

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (100 reviews)
"Great property, only if you like a royal treatment..."
Canada
Vinesh
The price is AU$279
includes taxes & fees
29 June - 30 June
Castello di Meleto

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
4.0 star property
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (396 reviews)
"Amazing staff, beautiful property, loved the courtyard. Really well located. Can't wait to stay again."
United States
Jason
The price is AU$217
includes taxes & fees
5 July - 6 July
Villa Casagrande Resort & SPA

Hotel Le Capanne

Hotel Le Capanne
3.0 star property
Arezzo
9.4 out of 10, Exceptional, (59 reviews)
"A very nice stay. Friendly and helpfull staff. Very nice Pool. Good breakfast outside. "
United States
Georg
The price is AU$192
includes taxes & fees
3 July - 4 July
Hotel Le Capanne
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Frequently asked questions

What is the best area to stay in Penna?
The best area to stay in Penna is within the historic centre of the town, particularly around Piazza della Repubblica and Corso Matteotti.

This central area is the heart of Penna, offering a quintessential Tuscan experience. It's characterised by narrow, winding cobblestone streets, mediaeval architecture, and charming piazzas. You'll find a good selection of trattorias, local shops selling artisan goods, and cafes, all within a short stroll. The Duomo di Penna, a prominent landmark, is also found here.

Couples looking for a romantic escape will find the historic centre particularly appealing. The evenings are pleasant for leisurely walks, enjoying aperitivos in a quiet piazza, and dining at authentic local restaurants. The convenience of having everything on your doorstep allows for a relaxed holiday without the need for constant travel.

For those seeking a more secluded and tranquil experience, the hills just outside Penna's historic walls offer beautiful villa and agriturismo options. These properties often come with stunning views of the Tuscan countryside, private pools, and larger spaces.
When is the best time to go to Penna?
The best time to go to Penna, Tuscany, Italy, is during the spring (April to June) and autumn (September to October) months. These periods offer pleasant weather, ideal for exploring the region's beauty without the intense summer heat or winter chill.

Spring in Penna sees the countryside burst into bloom, with comfortable temperatures ranging from 15°C to 25°C. This is an excellent time for outdoor activities such as hiking, cycling, and visiting vineyards. The olive groves and vineyards are particularly picturesque, and you'll find fewer crowds compared to the peak summer months.

Autumn also provides wonderful conditions, with temperatures typically between 18°C and 28°C. The landscape takes on beautiful golden and russet hues, and it's harvest season for grapes and olives, offering unique opportunities to experience local traditions. Many food and wine festivals take place during this time, making it great for food lovers.

While July and August offer warm, sunny weather, temperatures can often exceed 30°C, which can be quite hot for extensive sightseeing or outdoor activities. These months also see the highest number of visitors, meaning more crowded attractions and higher prices.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Penna.
How can I save on a hotel booking in Penna with Expedia?
One Keyā„¢ — Expedia's free travel rewards program—gives you instant access to perks and Member Prices on Penna hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Penna?
Prices for hotels in Penna often vary, but you can find a great deal from AU$74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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