𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Penna (2026)

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Our top choices for Penna hotels

A person pouring a liquid from a bottle into a glass.

A modern interior with a blue chair, a yellow chair, and a brown sofa. There is a glass door leading to an outdoor area with chairs and plants.

A glass table with a sandwich and a drink, a yellow sofa, and a fireplace with flames.

A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

1. Moody smart & comfy Hotel

Terranuova Bracciolini

Maurizio

S$169

includes taxes & fees

25 Sept - 26 Sept

A buffet with various food items and utensils.

A hotel room with a large bed, bedside tables, a nightstand, a vase with flowers, a tray with pastries, a teapot, and a glass of orange juice.

A modern lobby with a reception desk, two seating areas with orange chairs, and a marble floor.

A covered outdoor seating area with wicker furniture and a potted plant.

2. Hotel Il Viandante

Terranuova Bracciolini

Michelle

S$168

includes taxes & fees

11 Sept - 12 Sept

A spacious lobby with a reception desk, seating area, and a large vase.

A modern hotel lobby with a curved reception desk, seating area, and a bar.

A hotel room with a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.

A patio with a round table and chairs, potted plants, and a view of the building's interior.

3. Hotel Valdarno

Montevarchi

Emmanuel

S$157

includes taxes & fees

6 Oct - 7 Oct

A hotel room with a bed, a desk with a laptop, a chair, a nightstand, and a view through the window.

A hotel lobby with a reception desk, seating areas, and a dining area.

A gym with cardio machines, weightlifting equipment, and dumbbells.

A hotel with a sign reading "Michelangelo HOTEL".

4. Hotel Michelangelo

Terranuova Bracciolini

Sushil

S$149

includes taxes & fees

6 Oct - 7 Oct

A luxurious room with a chandelier, classical columns, and a dining area with wooden chairs and a table.

A bedroom with a bed, bedside tables, a desk, a chair, and a rug.

A traditional European town with stone buildings, a visible staircase, and a clear view of the surrounding hills.

A living room with a staircase, a sofa, a coffee table, and a rug.

5. Dimora Casa Eugenia

Loro Ciuffenna

Shannon

S$185

includes taxes & fees

7 Sept - 8 Sept

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

A modern reception area with a wooden reception desk, a metal bowl, potted plants, and a seating area with chairs.

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

6. Delta Hotel

Montevarchi

weixing

S$157

includes taxes & fees

6 Oct - 7 Oct

A stone building with outdoor seating and a pool in the background.

A dining table set with various foods, including meats, cheeses, and fruits.

A bedroom with two beds, a chandelier, a leopard-print chair, and a small table with a vase.

A stone house with a paved driveway and a lawn, surrounded by trees and a white car parked in front.

7. B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

S$196

includes taxes & fees

17 Sept - 18 Sept

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

A historic building with a stone facade, arched entrance, and a wooden balcony.

8. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Jason

S$226

includes taxes & fees

6 Oct - 7 Oct

A pool with a stone wall and a tree, surrounded by a clear sky and distant mountains.

A stone wall, a pink building, and a pool with a garden.

A bedroom with a large bed, bedside lamps, a chair, and a chandelier.

A room with a wooden door, a white cabinet with a book and candles, and two framed pictures on the wall.

9. Villa Barberino

Meleto

Natasa

S$201

includes taxes & fees

1 Oct - 2 Oct

A dining area with tables set for meals, chairs, and a window with a view.

A bedroom with a bed, bedside tables, a wall-mounted shelf, and a door.

A bathroom with a white sink, a mirror with a circular frame, and a shelf with toiletries.

A bed with a plaid bedspread, a metal headboard, and two wall-mounted lamps.

10. Boutique Hotel Fox's Inn

San Giustino Valdarno

S$132

includes taxes & fees

5 Oct - 6 Oct

A dining table set up outdoors with a view of a landscape.

A window seat with a view of a vineyard and distant mountains.

A historic building with multiple stories, surrounded by lush greenery and a well-maintained garden with a central fountain.

A hotel with a swimming pool, outdoor seating, and a view of the surrounding hills.

11. Il Borro - Relais & Châteaux

Loro Ciuffenna

Nichole

S$937

includes taxes & fees

27 Sept - 28 Sept

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

An interior corridor with arches, columns, and a brick wall.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

12. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

S$164

includes taxes & fees

8 Sept - 9 Sept

A well-maintained garden with geometric hedges and a pathway leading to a building with multiple windows and outdoor seating.

A cozy living room with a wooden ceiling, a television, a sofa, and a view of greenery outside.

A restaurant with tables set for dining, large umbrellas, and a view of the landscape.

A room with a large window offering a view of a vineyard and distant hills.

13. Palagina la Dimora

Figline e Incisa Valdarno

Tarek

S$92

includes taxes & fees

13 Sept - 14 Sept

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A modern living room with a white sofa, armchairs, and a coffee table.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

14. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

S$397

includes taxes & fees

6 Oct - 7 Oct

A traditional stone building with a garden featuring geometric hedges and potted plants.

A view of a garden with neatly trimmed hedges and a central water feature.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.

15. Badia a Coltibuono

Gaiole in Chianti

Thomas

S$329

includes taxes & fees

17 Sept - 18 Sept

A pool with lounge chairs and umbrellas, surrounded by a vineyard and mountains in the background.

A villa with a swimming pool, surrounded by olive groves and vineyards, set in a hilly landscape.

A spacious living area with a high ceiling and exposed beams, featuring a sofa set, a coffee table, and a dining table.

A hotel room with a bed, a tray with pastries, and a view of a stone building through open doors.

16. Borgo Iesolana Country Retreat

Bucine

costanza

S$301

includes taxes & fees

5 Oct - 6 Oct

A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.

A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

An aerial view of a villa surrounded by lush greenery and rolling hills.

An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.

17. Il Verreno

Ambra

Minna

S$390

includes taxes & fees

6 Sept - 7 Sept

A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.

An indoor dining area with tables set for two, large windows, and potted plants.

An outdoor dining area with tables and chairs, overlooking a scenic view of a coastal town during sunset.

A four-poster bed with a view of the outdoors, a desk with a chair, and a sofa in a room with wooden beams on the ceiling.

18. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

S$398

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with multiple tables and umbrellas, surrounded by greenery and hills in the background.

A resort with a large swimming pool, sun loungers, and umbrellas.

A modern bedroom with a large bed, a wooden headboard, a built-in bathtub, and a stone wall.

A large, two-story building with a covered outdoor seating area and a well-lit entrance.

19. Palagina la cascina

Figline e Incisa Valdarno

Peter

S$92

includes taxes & fees

7 Sept - 8 Sept

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

A hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.

A rooftop terrace with outdoor seating, a pergola, and a view of hills.

A spa area with a circular hot tub surrounded by mosaic tiles, a stone bench, and a small table with a bowl and a candle.

20. Il Gentiluomo Hotel & SPA

Arezzo

Luis Mauricio

S$111

includes taxes & fees

11 Sept - 12 Sept

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Top Penna Hotel Reviews

Villa Il Palagio

10/10 Excellent

"All staff very corteous and friendly"

Dievole Wine Resort

10/10 Excellent

"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"

Hu Norcenni Girasole Village

10/10 Excellent

"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."

Hotel Villa Campomaggio

10/10 Excellent

"Beautiful hotel room and location, definitely recommend!"

Castello Vicchiomaggio

10/10 Excellent

"Absolutely fantastic!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Such a beautiful and quiet property. The staff were so friendly and accommodating. The food and drinks were delicious and we enjoyed the spa as well!"

Belvedere di San Leonino

10/10 Excellent

"Staff is great. Room clean. Property beautiful and dinner was delicious"

La Certosa di Pontignano

10/10 Excellent

"Beautiful place, very quiet, in love with gardens"

Hotel Le Fontanelle

10/10 Excellent

"The hype around this hotel was absolutely worth it. Everything was incredibly clean and beautifully maintained, and the whole property exceeded our expectations. The food was excellent, the drinks were great, and the overall atmosphere made the stay feel really special. From the quality of the property to the dining and service, everything was top-notch. We would absolutely recommend staying here and would happily come back."

More cheap stays in Penna

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

S$71

6 Sept - 7 Sept

includes taxes & fees

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

S$86

9 Sept - 10 Sept

includes taxes & fees

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

S$269

7 Sept - 8 Sept

includes taxes & fees

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

Get rates

9.2/10 Wonderful! (5 reviews)

Agriturismo I Bonsi

VIA BONSI Reggello FI

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Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

Get rates

Frequently asked questions

Where is the best place to stay in Penna?

Borgo Scopeto Wine & Country Relais, located 17 mi (27.4 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 La Certosa di Pontignano and Villa Pitiana. 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 espresso maker. 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?

Borgo Scopeto Wine & Country Relais: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. Villa Pitiana and Castello di Spaltenna- Small Luxury Hotels of the World 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 12 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 Croce del Pratomagno, Fattoria La Vialla and Badia a Coltibuono. You'll also find Castello di Albola and Cantalici Winery 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.

Penna Hotels from S$71

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Penna

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Penna hotels

1. Moody smart & comfy Hotel

2. Hotel Il Viandante

3. Hotel Valdarno

4. Hotel Michelangelo

5. Dimora Casa Eugenia

6. Delta Hotel

7. B&B Country House Poggio del Drago

8. Villa Casagrande Resort & SPA

9. Villa Barberino

10. Boutique Hotel Fox's Inn

11. Il Borro - Relais & Châteaux

12. La Certosa di Pontignano

13. Palagina la Dimora

14. Chapter Chianti, a Member of Design Hotels

15. Badia a Coltibuono

16. Borgo Iesolana Country Retreat

17. Il Verreno

18. Villa Sassolini Country Boutique Hotel

19. Palagina la cascina

20. Il Gentiluomo Hotel & SPA

Top Penna Hotel Reviews

Villa Il Palagio

Dievole Wine Resort

Hu Norcenni Girasole Village

Hotel Villa Campomaggio

Castello Vicchiomaggio

Borgo Scopeto Wine & Country Relais

Belvedere di San Leonino

La Certosa di Pontignano

Hotel Le Fontanelle

More cheap stays in Penna

Hotel Chenno

Villa Norcenni Aparthotel

Castello di Bossi

Castello di Pratelli

Agriturismo I Bonsi

Tenuta La Pieve Casale Presciano

Frequently asked questions

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