Find hotels in Penna from NT$1,667

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Dec 26 - Dec 27
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Dec 27 - Dec 28
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Dec 26 - Dec 28
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Our top choices for Penna hotels

Exterior detail
La Certosa di Pontignano

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
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 NT$3,939
NT$4,481 total
includes taxes & fees
Dec 28 - Dec 29
La Certosa di Pontignano
1 bedroom, individually furnished, desk, soundproofing
Antiche Mura

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
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
Escape to this charming Italian affittacamere featuring a seasonal outdoor pool, poolside bar, and full-service spa. Located near La Salceta Winery and Il Borro Wines, guests enjoy free breakfast, WiFi, and parking. Children's pool adds family appeal.
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is NT$3,806
NT$4,187 total
includes taxes & fees
Jan 6 - 2026/1/7
Villa Cassia di Baccano
Terrace/patio
Cento Passi Dal Duomo

Cento Passi Dal Duomo

Cento Passi Dal Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (37)
Set in the heart of Arezzo, this cozy B&B is just a brief walk from Fraternita dei Laici and Museum of Means of Communication. Enjoy room service and easy access to Arezzo Station.
"Very well located to visit the town"
United States
Miguel
Cento Passi Dal Duomo
Restaurant
Borgo di Pietrafitta Relais

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 NT$3,974
NT$4,520 total
includes taxes & fees
Jan 3 - 2026/1/4
Borgo di Pietrafitta Relais
Interior detail
Hotel Palazzo San niccolò & Spa

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 NT$2,940
NT$3,456 total
includes taxes & fees
Jan 6 - 2026/1/7
Hotel Palazzo San niccolò & Spa
Seasonal outdoor pool, sun loungers
Castello di Meleto

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (91)
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
Exterior
B&B Country House Poggio del Drago

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
Seasonal outdoor pool
La Pensione di Vignamaggio

La Pensione di Vignamaggio

La Pensione di Vignamaggio
Panzano in Chianti
9.6 out of 10, Exceptional, (118)
Surrounded by Chianti countryside, this inviting pensione offers a seasonal outdoor pool and terrace for soaking up Tuscan sunshine. Enjoy complimentary breakfast before exploring nearby Church of Santa Maria Assunta. Comfortable rooms feature minibars and free WiFi.
"A beautiful location, fantastic view, close to wineries, little shops and local restaurants. "
Canada
Rob
La Pensione di Vignamaggio
Exterior
Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
9.2 out of 10, Wonderful, (99)
Nestled in Loro Ciuffenna, this luxurious Relais & Châteaux farmhouse offers rejuvenating spa treatments and Tuscan cuisine. Enjoy the poolside bar, fitness center, and complimentary WiFi while exploring nearby Il Borro Wines.
"A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia"
Canada
Ian
The price is NT$16,666
NT$18,332 total
includes taxes & fees
Jan 6 - 2026/1/7
Il Borro - Relais & Châteaux
Deluxe Room | Vineyard view
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (276)
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 NT$3,408
NT$3,971 total
includes taxes & fees
Jan 6 - 2026/1/7
Palazzo Leopoldo Dimora Storica & Spa
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Agriturismo Cuprena

Agriturismo Cuprena

Agriturismo Cuprena
Arezzo
9.6 out of 10, Exceptional, (20)
Immerse in Tuscan tranquility at this Arezzo agriturismo featuring indoor and seasonal outdoor pools. After savoring the complimentary breakfast, unwind in the sauna, work out at the fitness center, or enjoy drinks at the bar. Free parking and WiFi available.
"Extra friendly staff, personalized service, and a beautiful house with amazing accommodations. "
United States
Michelle
The price is NT$8,959
NT$10,077 total
includes taxes & fees
Dec 27 - Dec 28
Agriturismo Cuprena
Exterior
Albergo Villa San Michele

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 NT$4,318
NT$4,861 total
includes taxes & fees
Dec 31 - 2026/1/1
Albergo Villa San Michele
Balcony
Cameracaffè Centro

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
Enjoy magical Tuscan moments at this affittacamere with a scenic rooftop terrace. Just 2 minutes from Arezzo Station and near cultural gems like Piazza Guido Monaco, guests love the convenient daily buffet breakfast and complimentary WiFi.
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is NT$2,863
NT$3,371 total
includes taxes & fees
Jan 18 - 2026/1/19
Cameracaffè Centro
Exterior
Hotel Chenno

Hotel Chenno

Hotel Chenno
2.0 star property
Subbiano
7.8 out of 10, Good, (25)
Set in charming Subbiano near the train station, this family-friendly hotel offers convenient amenities including free WiFi, parking, and breakfast. Unwind at the terrace, grab a snack at the deli, or enjoy meals at Ristorante Chenno while exploring nearby castles.
"Gestione familiare ottima accoglienza nessun problema per i bagni esterni ottimo rapporto qualità prezzo "
Italy
pietro
The price is NT$1,515
NT$1,667 total
includes taxes & fees
Jan 8 - 2026/1/9
Hotel Chenno
Hallway
Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
3.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (198)
Tuscany countryside views await from the rooftop terrace of this charming hotel. Enjoy the outdoor pool with convenient poolside bar, savor regional specialties at the restaurant, and explore nearby Fashion Groove and The Mall Luxury Outlet.
"Amazing place !Food Resturant was the best including breakfast ❤️the staff will go out of there way for you and helpful with transportation if needed."
United States
Yolanda M
The price is NT$2,326
NT$2,614 total
includes taxes & fees
Jan 11 - 2026/1/12
Hotel Tenuta Il Burchio
Exterior
Borgo Casa al Vento

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
8.6 out of 10, Excellent, (38)
Escape to this Chianti countryside farm stay featuring 2 outdoor pools and a rooftop terrace. Indulge in local cuisine at the restaurant after exploring the on-site winery. Cantalici Winery and Medieval Tower of Barbischio await nearby.
"Cute secluded property l!"
United States
Courtney
The price is NT$4,957
NT$5,749 total
includes taxes & fees
Dec 29 - Dec 30
Borgo Casa al Vento
Pool
Torrebianca Tuscany

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 NT$2,946
NT$3,296 total
includes taxes & fees
Jan 18 - 2026/1/19
Torrebianca Tuscany
Free daily buffet breakfast
Casale La Gora

Casale La Gora

Casale La Gora
Figline e Incisa Valdarno
9.6 out of 10, Exceptional, (21)
Surrounded by rolling hills, this intimate B&B offers free breakfast and WiFi near Franciscan Monastery of St. Francis. Enjoy mountain biking adventures or relax by the outdoor pool after exploring nearby Figline Valdarno, just a 5-minute drive away.
"Casale La Gora in Tuscany. The property is beautifully renovated, blending historic charm with modern architecture. Our room was clean and cozy, the breakfast was delicious, and the pool was perfect for cooling off during the hot summer days. The host was warm, friendly, and always helpful, which made our stay even more enjoyable. We would definitely love to come back! "
Sweden
Besarta
The price is NT$3,235
NT$3,633 total
includes taxes & fees
Jan 11 - 2026/1/12
Casale La Gora
Outdoor pool, pool umbrellas, sun loungers
Le Lappe

Le Lappe

Le Lappe
Cavriglia
9.6 out of 10, Exceptional, (32)
Immerse yourself in Cavriglia's charm at this countryside retreat featuring an outdoor pool, hot tub, and rejuvenating sports massages. Savor Italian specialties at Giardino d'Inverno restaurant before exploring nearby Le Miccine attractions with convenient free parking and WiFi.
"Beautiful property in countryside Tuscany region ideal to stay for 2-7 days."
Canada
shrirang
Le Lappe
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
"It was a totally delightful experience. Our needs were taken care of, the Breakfast delicious and the meals at their restaurant superb. It was a perfect place to rest, relax and see Siena. "
Janice 3-night trip
Posted 2 months ago
La Certosa di Pontignano

More cheap stays in Penna

Hotel Chenno

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR
The price is NT$1,515 per night from Jan 8 to Jan 9
NT$1,515
NT$1,667 total
Jan 8 - 2026/1/9
includes taxes & fees
7.8/10 Good! (25 reviews)

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 Villa La Borghetta Resort and Hotel Continentale. See all available top hotels, or vacation rentals in Penna.
What are some of the best vacation rentals in Penna?
Borgo Argiano: Visitors like this Penna vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library. 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 La Borghetta Resort and Villa Casagrande Resort & SPA 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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