Find hotels in Penna from ¥8,231

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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, (502)
Soak in Tuscany from the rooftop terrace at this charming Castelnuovo Berardenga retreat. The on-site restaurant serves Italian cuisine throughout the day, while the garden setting creates a peaceful atmosphere. Terra di Seta and free perks like WiFi, parking, and breakfast add value.

"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is ¥9,728
¥11,433 total
includes taxes & fees
Dec 21 - Dec 22
La Certosa di Pontignano

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
Set amidst Castellina in Chianti, this family-friendly farm stay features an attached winery and refreshing outdoor pool. Enjoy complimentary WiFi and parking while exploring nearby Casa Vinicola Luigi Cecchi and Castellina Fortress, or unwind with massages and garden views.

"Wonderful setting."
United Kingdom
Simon
The price is ¥14,158
¥16,306 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Borgo di Pietrafitta Relais

Casa Ruffino

Casa Ruffino
Bagno a Ripoli
10.0 out of 10, Exceptional, (13)
Immerse yourself in Tuscan charm at this countryside winery. Take a refreshing dip in the seasonal outdoor pool, dine on local cuisine at Tre Rane Ruffino, and enjoy complimentary breakfast. Just a short drive from Florence's Piazzale Michelangelo and Pitti Palace.

"The best stay of my life "
United States
Oleksandr
Casa Ruffino

La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
10.0 out of 10, Exceptional, (110)
Surrounded by Tuscan beauty, this charming farm stay features its own winery and relaxing outdoor pool. Enjoy authentic regional cuisine at the restaurant and evening drinks at the bar. With free WiFi and parking, explore nearby Cassero Tower and Archaeological Museum.

"Stay was exceptional."
United States
Suzanne
La Cantina Relais - Fattoria Il Cipresso

Albergo Villa San Michele

Albergo Villa San Michele
Greve in Chianti
10.0 out of 10, Exceptional, (4)
Nestled in Greve in Chianti, this inviting hotel offers complimentary breakfast, WiFi, and parking. Visit nearby Querciabella and Castello di Albola after enjoying a meal at the restaurant or drinks at the bar.

"Loved this isolated escape within amazing proximity to historical vineyards and gorgeous landscapes."
Italy
Michael
The price is ¥21,327
¥24,009 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Albergo Villa San Michele

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)
Wake up to vineyard views at this charming B&B featuring a seasonal outdoor pool and complimentary breakfast. Just a 3-minute drive from Ponticino Station, this tranquil retreat offers easy access to the Buriano Bridge and Penna Natural Reserve.

"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

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (90)
Immerse yourself in authentic Tuscany at this historic castle estate. Enjoy wine tastings at the on-site winery, cool off in the seasonal outdoor pool, and dine at La Fornace di Meleto restaurant. Free WiFi and parking complement the beautiful garden and terrace settings.

"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

Locanda Il Gallo

Locanda Il Gallo
3.0 star property
Greve in Chianti
9.4 out of 10, Exceptional, (53)
Enjoy Italian countryside comfort at this Greve in Chianti hotel with complimentary breakfast and WiFi. After exploring nearby Sezzate and Verrazzano castles, unwind in the garden or savor drinks at the bar before ordering room service from the restaurant.

"The property owner was very helpful explaining wineries location and local food! The in-house restaurant was excellent and convenient! "
United States
Santina
The price is ¥23,697
¥26,616 total
includes taxes & fees
Dec 30 - Dec 31
Locanda Il Gallo

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (177)
Surrounded by Chianti vineyards, this spa hotel offers indulgent treatments, 2 restaurants, and both indoor and outdoor pools. Explore nearby Castello di Radda Winery or unwind at the poolside bar after a day in picturesque Tuscan countryside.

"Ideal country setting"
Canada
Dee
The price is ¥16,568
¥19,322 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Palazzo San niccolò & Spa

Relais La Torre

Relais La Torre
Arezzo
9.2 out of 10, Wonderful, (46)
Experience authentic Arezzo countryside living in this charming farm stay. Cool off in the seasonal outdoor and children's pools after exploring nearby Pieve di San Giovanni Battista. Free WiFi, parking, and onsite restaurant with terrace create a complete Italian retreat.

"Me, my family and my dog had the best time in this hotel, very peaceful and authentic."
Italy
Valentina
The price is ¥25,442
¥29,084 total
includes taxes & fees
Dec 16 - Dec 17
Relais La Torre

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (162)
Located in Terranuova Bracciolini, this welcoming hotel offers a cozy bar/lounge and convenient coffee shop. Just minutes from Il Cassero and a short drive from Montevarchi Station, guests consistently praise the attentive staff that enhance your Italian getaway.

"Arrived very late due to flight delay , communication and support from the hotel about late check in was fantastic and the owner even stayed until I arrived at 00.30. Recommended."
United Kingdom
James
The price is ¥13,724
¥18,755 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Il Viandante

Antiche Mura

Antiche Mura
Arezzo Centro Storico
9.4 out of 10, Exceptional, (86)
This cozy accommodation sits just a 12-minute walk from Arezzo Station. Explore nearby attractions like Fraternita dei Laici while enjoying convenient amenities including free WiFi, daily housekeeping, and laundry facilities.

"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

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (22)
Surrounded by Chianti's rolling hills, this guesthouse offers free breakfast, WiFi, and private pools. Visit nearby Sezzate and Verrazzano Castles, then return to savor a meal at the on-site restaurant after a day of exploring.

"Very well located in the heart if the Tuscany region."
United States
Eli
The price is ¥13,469
¥15,547 total
includes taxes & fees
Dec 16 - Dec 17
Casa di Palaia

Agriturismo La Forra

Agriturismo La Forra
Cavriglia
9.4 out of 10, Exceptional, (13)
Immerse yourself in Tuscany at this family-friendly farm stay featuring 2 outdoor pools and local cuisine at La Cucina de La Forra. Explore nearby attractions while enjoying free breakfast and parking, plus fitness center and terrace amenities.

"Loved it! Super helpful at check-in telling us about everything that was available. We wrote horses for two hours at a very affordable price. The restaurant on site was was good and breakfast was wonderful. Hiking trails and views were amazing. Would definitely stay again. Nearest grocery and shopping were only about 15 minutes away in montevechi."
United States
Joshua or Stephani
Agriturismo La Forra

Albergo San Lorenzo

Albergo San Lorenzo
3.0 star property
Poppi
8.6 out of 10, Excellent, (19)
Gaze across Poppi from this welcoming hotel's rooftop terrace after exploring nearby Castle and War Memorial. Enjoy complimentary WiFi, parking, and daily buffet breakfast. Adventure seekers can discover local hiking and mountain biking trails.

"Our journey was amazing in Poppi. Thanks for the Ladys for all helps and kindness. We had a great stay here! I highly recommend it."
France
Balázs
Albergo San Lorenzo

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (275)
This historic palazzo in Radda features indoor and outdoor pools plus a full-service spa offering deep-tissue massages. Savor local cuisine at La Perla del Palazzo restaurant, with Castello di Radda Winery nearby and free WiFi throughout.

"We loved it was easy to get to wineries or small towns we wanted to visit"
United States
Carol
The price is ¥14,847
¥17,429 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Palazzo Leopoldo Dimora Storica & Spa

Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti
8.8 out of 10, Excellent, (10)
Sip local wine at this Tuscan B&B's on-site winery, then enjoy free breakfast. Located near Castle of Brolio and San Felice Winery, this countryside retreat offers a restaurant, garden, and complimentary parking for vineyard adventures.

"Ricasoli is stunning, and nice place to stay nearby"
United States
Arturo
Brolio Agriroom

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40)
Immerse yourself in Rignano sull'Arno at this welcoming B&B offering complimentary cooked-to-order breakfast, WiFi, and parking. Located near Fashion Groove and The Mall Luxury Outlet, with Reggello Station just 4 minutes away by car.

"Lovely pool Breakfast good"
United Kingdom
christine
The price is ¥16,099
¥17,982 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Torrebianca Tuscany

Agriturismo Montemagni di Sopra

Agriturismo Montemagni di Sopra
Greve in Chianti
9.0 out of 10, Wonderful, (8)
Overlooking the pastoral hills of Greve in Chianti, this charming farm stay invites guests to unwind at the seasonal outdoor pool. On-site winery and restaurant showcase local flavors, while Verrazzano and Sezzate castles wait nearby to be explored.

"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
The price is ¥14,966
¥17,194 total
includes taxes & fees
Dec 16 - Dec 17
Agriturismo Montemagni di Sopra

AZIENDA AGRICOLO IL POGGIOLINO

AZIENDA AGRICOLO IL POGGIOLINO
Pelago
Discover this charming countryside retreat offering complimentary local cuisine breakfast daily. Explore the property's hiking and biking trails, then unwind on the rooftop terrace with panoramic views. Nearby attractions include Castello di Nipozzano, just a short drive from Pontassieve Station.
The price is ¥18,707
¥20,944 total
includes taxes & fees
Dec 16 - Dec 17
AZIENDA AGRICOLO IL POGGIOLINO
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

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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 traveler data. Other good choices for your trip to the area are Hotel Continentale and Villa Casagrande Resort & SPA. See all available top hotels, or vacation rentals in Penna.
What are some of the best vacation rentals in Penna?
Agriturismo La Ferrozzola: You might want to consider this vacation home rental near Penna, which offers a terrace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware. You and your friends and family can relax into your vacation with amenities like a selection of games. 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 that most hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Penna.
Where can I learn more about changing or cancelling my trip to Penna?
For additional details about rescheduling or cancelling your trip to Penna, head over to our customer service page.
What's the best pet-friendly hotel in Penna?
Break House Hotel is a top hotel for people traveling 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 Casagrande Resort & SPA and Villa La Borghetta Resort are two additional hotels with an onsite pool. View all hotels with pools in Penna.
What's it like staying in Penna?
Travelers to Penna will find plenty to explore and enjoy. In Penna, there are 8 hotels and other accommodations to choose from. Find out more about Penna.
What should I see while I'm in 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. Check out what more 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 temp of 71°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Penna is 36 inches.

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