Top 10 Hotels in Penna (from $52) 2026 - Competitive Prices

Our top choices for Penna hotels

Hotel

Chapter Chianti, a Member of Design Hotels

Cavriglia

$300 nightly

Aug 3 - Aug 4

Total with taxes and fees

Castello Vicchiomaggio

Greve in Chianti

Ruth

$170 nightly

Jul 19 - Jul 20

Total with taxes and fees

Casa Ruffino

Bagno a Ripoli

Oleksandr

$272 nightly

Aug 10 - Aug 11

Total with taxes and fees

Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

$222 nightly

Aug 6 - Aug 7

Total with taxes and fees

La Certosa di Pontignano

Castelnuovo Berardenga

Ken

$122 nightly

Jul 20 - Jul 21

Total with taxes and fees

Azienda agricola la camporena

Greve in Chianti

$132 nightly

Jul 19 - Jul 20

Total with taxes and fees

Torre a Cona Wine Estate

Rignano sull'Arno

Tom

$277 nightly

Jul 19 - Jul 20

Total with taxes and fees

Castello Di Montemasso

Greve in Chianti

Quan

$122 nightly

Aug 2 - Aug 3

Total with taxes and fees

Premium bedding, down comforters, memory foam beds, minibar

Casale La Gora

Figline e Incisa Valdarno

Caleb

$119 nightly

Aug 9 - Aug 10

Total with taxes and fees

Castello di Meleto

Gaiole in Chianti

Vinesh

$186 nightly

Jul 17 - Jul 18

Total with taxes and fees

Agriturismo San Sano

Gaiole in Chianti

Shawn

$128 nightly

Jul 19 - Jul 20

Total with taxes and fees

Castello di Fonterutoli Wine Resort

Castellina in Chianti

Giancarlo

$153 nightly

Jul 18 - Jul 19

Total with taxes and fees

Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

$140 nightly

Aug 2 - Aug 3

Total with taxes and fees

Fondaco del Moro

Civitella in Val di Chiana

Heather

$70 nightly

Jul 19 - Jul 20

Total with taxes and fees

Il Borro - Relais & Châteaux

Loro Ciuffenna

Miguel A

$610 nightly

Aug 12 - Aug 13

Total with taxes and fees

B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

$125 nightly

Jul 26 - Jul 27

Total with taxes and fees

Agriturismo il Casolare - Villa Vettori

Poppi

Mahboubul

$123 nightly

Jul 21 - Jul 22

Total with taxes and fees

Dievole Wine Resort

Castelnuovo Berardenga

Pamela

$351 nightly

Jul 22 - Jul 23

Total with taxes and fees

Castello di Volpaia

Radda in Chianti

Mark

$260 nightly

Aug 12 - Aug 13

Total with taxes and fees

Locanda Il Gallo

Greve in Chianti

Santina

$120 nightly

Aug 16 - Aug 17

Total with taxes and fees

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Top Penna Hotel Reviews

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Borgo refers to something like little village and that’s what this property is. A cluster of beautiful stone buildings and gravel drives surrounded by acres of olive and lavender. Beautifully appointed common and areas in rooms. Excellent restaurant with elevated cuisine. Beautiful pool. Distance skyline view of Sienna, Really no negatives. Would definitely come back."

Hotel Le Fontanelle

10/10 Excellent

"The photos might hint at the quality of the property but don’t really do it justice. The sweeping easterly, vineyard views across to Monti-in-Chianti and up to Brolio are really mesmerizing. Grounds were well kept. Breakfast had the usual Italian selection of good fruits, grains, meats, breads, and sweets. Coupled with a limited menu of ala carte items and rich cappuccinos! Our suite was located about .25mi south of the main building. We enjoyed the walk multiple times per day but grandma might not. The room was nicely appointed with a living room, large bedroom, closet space and two sink bathroom. Stocked mini-fridge and cof/tea selections. Each room had its own outdoor area with a table/chaise to enjoy with coffee or after the pool. The out door pool is not heated (indoor pool is) but very comfortable on the 90 degree days we spent there. Pool service isn’t quite the same as some resorts, as you would go to the bar to order food/beverage and they’d bring it out to your chair setup. A good selection of menu items are available to choose from. Restaurants on site were excellent. Had the Bistecca at Tuscanio and it was perfection while LaColonna’s carpaccio and fusilli dish were both a treat. Staff was friendly though a bit harried. Seemed like they just needed a few more bodies around to smooth out the place. Ilaria at the front desk was really outstanding with her command and knowledge. While Marcella really made the pool with her wry smile and daily daiquiri selection."

Palagina la cascina

10/10 Excellent

"We enjoyed our stay at Palagina SO MUCH! I wanted to add another night but our schedule didn't allow. The room had an amazing view to wake up to each morning, it was clean, the pool was awesome (especially the shallow kids section) The grounds and property were absolutely beautiful. We had a rough and stressful day and getting to Palagina really made everything better. It was also great that restaurants and food options were within a 10 minute drive. If we ever get to visit Tuscany again I would absolutely come back."

Hotel Continentale

8/10 Good

"The most prominent feature of this hotel is the terrace, what a fabulous view! The staff were very helpful and friendly, showing the Gym which is slightly hidden away behind the bar and the large relaxing public lounge. There is a wide offer for breakfast in a large room which I think is underused. It would for instance be a great place for a reception or other formal gathering."

More cheap stays in Penna

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

$47 nightly

$52 total

Jul 19 - Jul 20

Total with taxes and fees

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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Our top choices for Penna hotels

Chapter Chianti, a Member of Design Hotels

Castello Vicchiomaggio

Casa Ruffino

Castello di Tornano Wine Resort

La Certosa di Pontignano

Azienda agricola la camporena

Torre a Cona Wine Estate

Castello Di Montemasso

Casale La Gora

Castello di Meleto

Agriturismo San Sano

Castello di Fonterutoli Wine Resort

Borgo di Pietrafitta Relais

Fondaco del Moro

Il Borro - Relais & Châteaux

B&B Country House Poggio del Drago

Agriturismo il Casolare - Villa Vettori

Dievole Wine Resort

Castello di Volpaia

Locanda Il Gallo

Top Penna Hotel Reviews

Borgo Scopeto Wine & Country Relais

More cheap stays in Penna

Hotel Chenno

Frequently asked questions

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