Find hotels in Penna from ฿1,647

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26 Dec - 27 Dec
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27 Dec - 28 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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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 ฿3,893
฿4,429 total
includes taxes & fees
28 Dec - 29 Dec
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 cosy 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 ฿3,762
฿4,138 total
includes taxes & fees
6 Jan - 7 Jan 2026
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 cosy 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 ฿2,862
฿3,294 total
includes taxes & fees
8 Jan - 9 Jan 2026
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 ฿2,906
฿3,416 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Palazzo San niccolò & Spa
Seasonal outdoor pool, pool 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 centre, 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 ฿16,472
฿18,119 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (275)
This historic palazzo in Radda features indoor and outdoor pools plus a full-service spa offering deep-tissue massages. Savour 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 ฿3,368
฿3,925 total
includes taxes & fees
6 Jan - 7 Jan 2026
Palazzo Leopoldo Dimora Storica & Spa
Indoor pool, seasonal outdoor pool, pool umbrellas, pool 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 savouring the complimentary breakfast, unwind in the sauna, work out at the fitness centre, 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 ฿8,852
฿9,956 total
includes taxes & fees
27 Dec - 28 Dec
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 ฿4,268
฿4,804 total
includes taxes & fees
31 Dec - 1 Jan 2026
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 ฿2,829
฿3,332 total
includes taxes & fees
18 Jan - 19 Jan 2026
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 ฿1,497
฿1,647 total
includes taxes & fees
8 Jan - 9 Jan 2026
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, savour regional specialities 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 ฿2,299
฿2,583 total
includes taxes & fees
11 Jan - 12 Jan 2026
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 ฿4,900
฿5,682 total
includes taxes & fees
28 Dec - 29 Dec
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 ฿2,911
฿3,257 total
includes taxes & fees
18 Jan - 19 Jan 2026
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 ฿3,196
฿3,589 total
includes taxes & fees
11 Jan - 12 Jan 2026
Casale La Gora
Outdoor pool, pool umbrellas, pool 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. Savour Italian specialities 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

More cheap stays in Penna

Hotel Chenno

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR
The price is ฿1,497 per night from 8 Jan to 9 Jan
฿1,497
฿1,647 total
8 Jan - 9 Jan 2026
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 traveller 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 holiday rentals that Penna has to offer?
Borgo Argiano: This holiday home rental outside of Penna is located on a river, and has a balcony, a terrace and a BBQ 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 holiday 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 most hotel bookings are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Penna.
What's the best dog-friendly hotel in Penna?
Break House Hotel is a top hotel for people travelling 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 that feature an on-site pool. View all hotels with pools in Penna.
What's it like to stay in Penna?
Travellers to Penna will find plenty to explore and enjoy. In Penna, there are 8 hotels and other accommodation options to choose from. Find out more about Penna.
What should I do while I'm visiting 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. Take a look at what more there is 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 temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Penna is 902 mm.

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