Top 10 Hotels in Penna in 2026 (from $71)

Q: What accommodations do travelers like in Penna?

Guests like Hu Norcenni Girasole Village , Palagina la Dimora and Chapter Chianti, a Member of Design Hotels .

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1. Hotel Il Viandante

Terranuova Bracciolini

$126 total

includes taxes & fees

Dec 11 - Dec 12

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

2. Moody smart & comfy Hotel

Terranuova Bracciolini

$126 total

includes taxes & fees

Nov 26 - Nov 27

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

3. Delta Hotel

Montevarchi

$140 total

includes taxes & fees

Nov 26 - Nov 27

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

4. Hotel Valdarno

Montevarchi

$130 total

includes taxes & fees

Nov 15 - Nov 16

A courtyard with stone flooring, arched walkways, and a central fountain.

5. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

$104 total

includes taxes & fees

Dec 13 - Dec 14

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

6. Boutique Hotel Fox's Inn

San Giustino Valdarno

$101 total

includes taxes & fees

Nov 19 - Nov 20

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

7. Hotel Michelangelo

Terranuova Bracciolini

$120 total

includes taxes & fees

Dec 6 - Dec 7

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

8. Dimora Casa Eugenia

Loro Ciuffenna

$142 total

includes taxes & fees

Nov 26 - Nov 27

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

9. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

$176 total

includes taxes & fees

Nov 13 - Nov 14

A cozy living room with a stone wall, a wine rack, and two sofas.

10. Villa Cassia di Baccano

Loro Ciuffenna

$104 total

includes taxes & fees

Nov 26 - Nov 27

An outdoor patio area with a brick archway, potted plants, and wicker furniture.

11. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

$91 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor dining area with tables and chairs, a pergola, and a view of distant mountains.

12. Albergo San Lorenzo

Poppi

$97 total

includes taxes & fees

Nov 26 - Nov 27

A bedroom with a stone wall, a bed, a nightstand, a window, and a mirror.

13. Casale La Gora

Figline e Incisa Valdarno

$86 total

includes taxes & fees

Dec 1 - Dec 2

A modern lobby with a bar area, seating, and a large window.

14. Hotel Toscana

Figline e Incisa Valdarno

$141 total

includes taxes & fees

Dec 7 - Dec 8

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

15. Palagina la cascina

Figline e Incisa Valdarno

$83 total

includes taxes & fees

Nov 13 - Nov 14

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building with a balcony.

16. Hotel Fattoria degli Usignoli

Reggello

$121 total

includes taxes & fees

Dec 8 - Dec 9

A cozy room with a wooden floor, a sofa, a table with a glass, and a view through a window.

17. Villa Barberino

Meleto

$187 total

includes taxes & fees

Nov 23 - Nov 24

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

18. Il Borro - Relais & Châteaux

Loro Ciuffenna

$479 total

includes taxes & fees

Nov 29 - Nov 30

A restaurant with a bar area, wooden furniture, and a potted plant.

19. Hotel Rifugio la Foresta

Reggello

$91 total

includes taxes & fees

Nov 13 - Nov 14

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

20. B&B Country House Poggio del Drago

Civitella in Val di Chiana

$107 total

includes taxes & fees

Nov 22 - Nov 23

View all properties

Go beyond your typical stay in Penna

Check out reviews of Penna hotels guests love

Hotel Il Viandante

Terranuova Bracciolini

10/10 Exceptional

Michelle

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

10/10 Exceptional

Anonymous traveler

Il Borro - Relais & Châteaux

Loro Ciuffenna

10/10 Exceptional

Il Borro truly hit all marks for a unique and luxurious stay in Tuscany. The location is a bit removed from the traditional or well-traveled parts of Tuscany, but is perfect if you are seeking quiet, rural and unblemished landscapes. One tip: arrive early (before dark) as the estate is sprawling and GPS sends you in a different direction than reception. We were pleasantly surprised that our 2-room suite in the Il Borro village (different than the Villa) was in fact a 2-bedroom house with a...

David

A spacious dining area with multiple tables and chairs, a bar area with shelves of bottles, and a large window providing a view of the outdoors.

Viesca Toscana Suites & Villas

Reggello

10/10 Exceptional

Jessica

Casale La Gora

Figline e Incisa Valdarno

10/10 Exceptional

We had the most wonderful time at Casale La Gora. Francesca was super sweet and helpful! We spent 5 nights there and enjoyed every second of it. The room was spacious and comfortable, I missed a bench or couch at night when we were relaxing and extra pillows would have been handy, however the house has two guest lounge rooms with comfy sits. Breakfast was delicious and we enjoyed the variety of different deserts/cakes every day. Our host made sure there was always well stocked and she made a...

Miguel A

Hotel Michelangelo

Terranuova Bracciolini

10/10 Exceptional

Sushil

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Exceptional

Kristen

A stone building with a yellow sign reading "b&b erioico".

L' Eroico

Gaiole in Chianti

10/10 Exceptional

Angela

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

Badia a Coltibuono

Gaiole in Chianti

10/10 Exceptional

Grace

Frequently Asked Questions

What accommodations do travelers like in Penna?

Guests like Hu Norcenni Girasole Village, Palagina la Dimora and Chapter Chianti, a Member of Design Hotels.

Can I book refundable accommodations in Penna?

If you need the flexibility to change your plans to Penna, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Penna if I want a vacation home instead of a hotel?

Browse 6 vacation homes on our site.

What will the weather in Penna be like during my visit?

August and July are typically the warmest months in Penna when the average temp is 71°F. January and February are the coldest months when the average temperature is 42°F. November and October are the months with the most rain.

Why should I book my Penna hotel with Hotels.com?

There are lots of reasons to book your Penna trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.