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Check prices for these dates

This weekend
May 22 - May 24
Next weekend
May 29 - May 31

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Our top choices for Penna hotels

Free daily continental breakfast

HOTEL PLANET INTERNATIONAL

HOTEL PLANET INTERNATIONAL
Arezzo
$69 nightly
The price is $83
Jun 7 - Jun 8
Total with taxes and fees
HOTEL PLANET INTERNATIONAL
Seasonal outdoor pool

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (382 reviews)
"Great views and property. Staff were all very nice"
Canada
Steven
$217 nightly
The price is $238
Jun 17 - Jun 18
Total with taxes and fees
Castello Vicchiomaggio
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
$275 nightly
The price is $310
May 28 - May 29
Total with taxes and fees
2 Cuori e 1 Yurta Glamping in Toscana
Snack bar

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (534 reviews)
"Magical location"
United States
Arthur
$146 nightly
The price is $170
Jun 10 - Jun 11
Total with taxes and fees
La Certosa di Pontignano
Exterior

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (89 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
$122 nightly
The price is $139
Jun 5 - Jun 6
Total with taxes and fees
Agriturismo San Sano
Terrace/patio

VioVillas Agriturismo Glamping Arezzo

VioVillas Agriturismo Glamping Arezzo
Arezzo
$95 nightly
The price is $112
May 24 - May 25
Total with taxes and fees
VioVillas Agriturismo Glamping Arezzo
Exterior

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.0 out of 10, Wonderful, (105 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
$240 nightly
The price is $273
May 27 - May 28
Total with taxes and fees
Castello di Tornano Wine Resort
Garden

Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Excellent spacious rooms. Spectacular view on Florence and vineyards. Impressive breakfast room and beautiful property Quiet and peaceful Perfect service"
United States
Patrick
$143 nightly
The price is $158
May 31 - Jun 1
Total with taxes and fees
Castello Di Montemasso
Restaurant

Locanda Il Gallo

Locanda Il Gallo
3.0 star property
Greve in Chianti
9.4 out of 10, Exceptional, (53 reviews)
"The property owner was very helpful explaining wineries location and local food! The in-house restaurant was excellent and convenient! "
United States
Santina
$109 nightly
The price is $123
Jun 3 - Jun 4
Total with taxes and fees
Locanda Il Gallo
Exterior

Torre a Cona Wine Estate

Torre a Cona Wine Estate
Rignano sull'Arno
9.6 out of 10, Exceptional, (93 reviews)
"This exceeded our expectations (which were already high) in every way possible. The accommodation and setting is everything you want from a castello in Tuscany. The local walks were breathtakingly beautiful and we can’t wait to return."
United Kingdom
Katie
$267 nightly
The price is $297
Jun 2 - Jun 3
Total with taxes and fees
Torre a Cona Wine Estate
Continental breakfast for a fee

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (164 reviews)
"Our girls loved having the upstairs to themselves, the staff was friendly and helpful, and the breakfast was *delicious!*"
United States
Michelle
$113 nightly
The price is $131
May 24 - May 25
Total with taxes and fees
Hotel Il Viandante
Outdoor pool, sun loungers

Le Cetinelle B&B

Le Cetinelle B&B
Greve in Chianti
9.8 out of 10, Exceptional, (93 reviews)
"We loved our stay here, our only regret is that we didn’t stay longer. The staff was very friendly and helpful. The views were amazing and the breakfast was very good. Definitely coming back here if we make another trip to Italy. "
United States
Wayne
$122 nightly
The price is $139
Jun 2 - Jun 3
Total with taxes and fees
Le Cetinelle B&B
Seasonal outdoor pool, sun loungers

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (98 reviews)
"Absolutely perfect. Everything about this property is perfect."
United States
Steven
$223 nightly
The price is $255
May 31 - Jun 1
Total with taxes and fees
Castello di Meleto
Snack bar

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
$101 nightly
The price is $117
Jun 16 - Jun 17
Total with taxes and fees
Hotel Rifugio la Foresta
Restaurant

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (175 reviews)
"Wonderful setting."
United Kingdom
Simon
$149 nightly
The price is $168
Jun 8 - Jun 9
Total with taxes and fees
Borgo di Pietrafitta Relais
Horseback riding

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
9.2 out of 10, Wonderful, (103 reviews)
"The views were spectacular along with the food"
United States
cory
$666 nightly
The price is $733
Jun 8 - Jun 9
Total with taxes and fees
Il Borro - Relais & Châteaux
Exterior

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, (61 reviews)
"Great stay - everything was perfect. Super friendly host and really calm atmosphere."
Germany
Yannick
$92 nightly
The price is $101
May 24 - May 25
Total with taxes and fees
B&B Country House Poggio del Drago
Exterior

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.4 out of 10, Exceptional, (43 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
$70 nightly
The price is $77
May 24 - May 25
Total with taxes and fees
Fondaco del Moro
Exterior

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (209 reviews)
"Very peaceful and staff was very helpful with reservations for excursions"
United States
Giancarlo
$207 nightly
The price is $232
May 26 - May 27
Total with taxes and fees
Castello di Fonterutoli Wine Resort
Exterior

Castello La Leccia

Castello La Leccia
Castellina in Chianti
10.0 out of 10, Exceptional, (105 reviews)
"Amazing location, very attentive staff. Excellent restaurant for breakfast and dinner. Easy driving to nearby towns. Would highly recommend."
United States
Boris
$380 nightly
The price is $423
Jun 12 - Jun 13
Total with taxes and fees
Castello La Leccia
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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"A wonderful experience from beginning to end. I would highly recommend!"
Robert 1-night trip
Posted 9 hours ago
La Certosa di Pontignano

More cheap stays in Penna

Hotel Chenno

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR
$48 nightly
The price is $52 total per night from May 24 to May 25
$52 total
May 24 - May 25
Total with taxes and fees

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Frequently asked questions

What is the best area to stay in Penna?
The best area to stay in Penna, Tuscany, is directly within the historic center of Penna, or in the surrounding countryside just outside the town walls.

The historic center of Penna is ideal for those who appreciate being within walking distance of local life. You'll find yourself amidst narrow cobblestone streets, traditional Tuscan architecture, and local shops and eateries. The main piazza, Piazza Amerighi, serves as a central gathering point, often hosting local markets. This area is particularly well-suited for solo travelers or couples who enjoy exploring on foot and experiencing the town's daily rhythms.

For those seeking a more tranquil experience with scenic views, the countryside immediately surrounding Penna offers excellent options. Here, you'll find villas and farmhouses located among olive groves and vineyards, often boasting amenities like private pools and expansive gardens.
When is the best time to go to Penna?
The best times to go to Penna, Tuscany, are during the shoulder seasons of April to May and September to October. These periods offer pleasant weather, fewer crowds, and the best opportunities to experience the region's culinary and scenic highlights.

For those interested in exploring the Tuscan countryside, late spring (April-May) is ideal. The landscapes are lush and green, wildflowers are in bloom, and the temperatures are comfortable for outdoor activities like hiking or vineyard tours. It's also a wonderful time to enjoy al fresco dining as the days grow longer.

Couples looking for a romantic getaway will find early autumn (September-October) perfect. The grape harvest season brings a special vibrancy to the vineyards, and the changing foliage creates stunning backdrops for scenic drives.
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 canceled 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 Penna hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Penna hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Penna hotel?
Prices for hotels in Penna often vary, but you can find a great deal from $52 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 the cheapest rate.

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