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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, (508 reviews)
"Excellent place to stay even for the next time. "
Canada
Xuejie
$108 nightly
The price is $124
Feb 14 - Feb 15
Total with taxes and fees
La Certosa di Pontignano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$119 nightly
The price is $131
Jan 26 - Jan 27
Total with taxes and fees
Villa Cassia di Baccano

Agriturismo Montemagni di Sopra

Agriturismo Montemagni di Sopra
Greve in Chianti
9.0 out of 10, Wonderful, (8 reviews)
"The hostess is very accommodating and sweet. The beds were incredibly comfy and shower was spacious. A very lovely and peaceful stay! "
United States
Rachel
$95 nightly
The price is $109
Jan 20 - Jan 21
Total with taxes and fees
Agriturismo Montemagni di Sopra

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (93 reviews)
"We had a great time"
United States
Anna
$152 nightly
The price is $177
Jan 20 - Jan 21
Total with taxes and fees
Castello di Meleto

Castello di Bossi

Castello di Bossi
2.0 star property
Castelnuovo Berardenga
7.8 out of 10, Good, (8 reviews)
"The location is great if you get to the hotel in a car. "
Mexico
CESAR JAVIER
$146 nightly
The price is $167
Jan 24 - Jan 25
Total with taxes and fees
Castello di Bossi

VioVillas Agriturismo Glamping Arezzo

VioVillas Agriturismo Glamping Arezzo
Arezzo
$107 nightly
The price is $124
Jan 21 - Jan 22
Total with taxes and fees
VioVillas Agriturismo Glamping Arezzo

La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
10.0 out of 10, Exceptional, (110 reviews)
"Stay was exceptional."
United States
Suzanne
$152 nightly
The price is $174
Jan 25 - Jan 26
Total with taxes and fees
La Cantina Relais - Fattoria Il Cipresso

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (162 reviews)
"Our girls loved having the upstairs to themselves, the staff was friendly and helpful, and the breakfast was *delicious!*"
United States
Michelle
$109 nightly
The price is $126
Feb 15 - Feb 16
Total with taxes and fees
Hotel Il Viandante

Casa Ruffino

Casa Ruffino
Bagno a Ripoli
10.0 out of 10, Exceptional, (13 reviews)
"The best stay of my life "
United States
Oleksandr
$219 nightly
The price is $241
Feb 16 - Feb 17
Total with taxes and fees
Casa Ruffino

Relais La Torre

Relais La Torre
Arezzo
9.2 out of 10, Wonderful, (47 reviews)
"Me, my family and my dog had the best time in this hotel, very peaceful and authentic."
Italy
Valentina
$194 nightly
The price is $220
Jan 31 - Feb 1
Total with taxes and fees
Relais La Torre

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (179 reviews)
"Ideal country setting"
Canada
Dee
$95 nightly
The price is $111
Jan 26 - Jan 27
Total with taxes and fees
Hotel Palazzo San niccolò & Spa

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (22 reviews)
"Very well located in the heart if the Tuscany region."
United States
Eli
$85 nightly
The price is $99
Jan 20 - Jan 21
Total with taxes and fees
Casa di Palaia

I Salici Agriturismo

I Salici Agriturismo
Pergine Valdarno
9.8 out of 10, Exceptional, (6 reviews)
"We had an amazing stay at this property. The pictures do not do it justice - it is tremendously beautiful. Marco and team were warm, welcoming and incredibly generous. Thank you for an unforgettable stay. We will be back!"
Canada
Chanel
$139 nightly
The price is $153
Feb 4 - Feb 5
Total with taxes and fees
I Salici Agriturismo

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
$270 nightly
The price is $305
Jan 28 - Jan 29
Total with taxes and fees
2 Cuori e 1 Yurta Glamping in Toscana

Hotel Chenno

Hotel Chenno
2.0 star property
Subbiano
7.8 out of 10, Good, (25 reviews)
"Chambre spacieuse lit confortable c'est propre ...douche/wc c'est dans le couloir Personnel super gentils Parking en face et sur le côté de l'hôtel . Petit déjeuner simple ( ça manque du pain frais) biscottes beurre confiture gâteau au coco petit croissants aux abricots .... Si non dans l'ensemble petit hôtel chaleureux A revenir une prochaine fois "
France
Henri Pierre
$47 nightly
The price is $52
Jan 20 - Jan 21
Total with taxes and fees
Hotel Chenno

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (277 reviews)
"Excellent breakfast. "
Canada
Karen
$117 nightly
The price is $136
Feb 2 - Feb 3
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
$136 nightly
The price is $159
Feb 19 - Feb 20
Total with taxes and fees
L' Eroico

La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
9.6 out of 10, Exceptional, (119 reviews)
"A beautiful location, fantastic view, close to wineries, little shops and local restaurants. "
Canada
Rob
$151 nightly
The price is $167
Feb 19 - Feb 20
Total with taxes and fees
La Pensione di Vignamaggio

THE MONNA LISA RESORT

THE MONNA LISA RESORT
Arezzo
9.2 out of 10, Wonderful, (9 reviews)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
$116 nightly
The price is $135
Jan 25 - Jan 26
Total with taxes and fees
THE MONNA LISA RESORT

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40 reviews)
"Lovely pool Breakfast good"
United Kingdom
christine
$85 nightly
The price is $95
Feb 1 - Feb 2
Total with taxes and fees
Torrebianca Tuscany
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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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