Top 10 Hotels in Penna (from $54) 2026 - Competitive Prices

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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

Rocco

$113 nightly

$128 total

Oct 24 - Oct 25

Total with taxes and fees

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

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

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

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

2. Hotel Valdarno

Montevarchi

Emmanuel

$103 nightly

$113 total

Nov 15 - Nov 16

Total with taxes and fees

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.

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

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

3. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

$104 nightly

$117 total

Nov 15 - Nov 16

Total with taxes and fees

A buffet with various food items and utensils.

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

A hotel entrance with a sign reading "HOTEL il Viandante".

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

4. Hotel Il Viandante

Terranuova Bracciolini

Michelle

$107 nightly

$123 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

A neatly arranged bedroom with a bed, bedside tables, a lamp, a wall-mounted clock, and a basket.

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

5. Boutique Hotel Fox's Inn

San Giustino Valdarno

Peter

$87 nightly

$96 total

Oct 30 - Oct 31

Total with taxes and fees

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

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.

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

A hotel room with a bed, a TV, a desk, and a mirror.

6. Delta Hotel

Montevarchi

weixing

$108 nightly

$119 total

Nov 15 - Nov 16

Total with taxes and fees

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 bed, bedside tables, a large wooden wardrobe, a bathroom with a bathtub, and a window with a view.

A modern living room with a sectional sofa, a glass coffee table, wooden flooring, and exposed brick walls.

7. Villa Barberino

Meleto

Claire

$126 nightly

$138 total

Nov 15 - Nov 16

Total with taxes and fees

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 hotel with a sign reading "Michelangelo HOTEL".

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

8. Hotel Michelangelo

Terranuova Bracciolini

Sushil

$107 nightly

$121 total

Nov 15 - Nov 16

Total with taxes and fees

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

An outdoor patio with tables and chairs, potted plants, and a view of the cityscape.

A buffet area with various food items, condiments, and a refrigerator.

A hotel entrance with a covered staircase, potted plants, and a sign indicating it is a hotel and restaurant.

9. Hotel Toscana

Figline e Incisa Valdarno

Anonymous traveler

$128 nightly

$142 total

Nov 15 - Nov 16

Total with taxes and fees

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

A dining area with a fireplace, wooden beams, and a tiled floor.

A swimming pool with steps leading into it, surrounded by lounge chairs and a stone wall with greenery.

A room with a large window, a radiator, and a television on a stand.

10. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

$72 nightly

$81 total

Nov 3 - Nov 4

Total with taxes and fees

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

A poolside area with lounge chairs and a swimming pool.

An outdoor dining area with tables and chairs, a stone wall, and a wooden ceiling.

A patio area with a gravel path, wooden chairs, and a table. There is a building with a stone wall and a door.

11. Casale La Gora

Figline e Incisa Valdarno

Roberto

$68 nightly

$77 total

Nov 8 - Nov 9

Total with taxes and fees

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

A modern kitchen with a large window, wooden ceiling, and a view of a forested area.

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

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

12. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

$269 nightly

$303 total

Oct 20 - Oct 21

Total with taxes and fees

A swimming pool with a stone border, surrounded by lounge chairs and a stone wall.

A pathway flanked by tall cypress trees and various shrubs, leading to a yellow building with green shutters.

An aerial view of a villa with a swimming pool, surrounded by lush greenery and tall trees.

An outdoor restaurant with tables set for dining, overlooking a swimming pool and lush greenery.

13. Villa Rigacci

Reggello

Thomas

$132 nightly

$153 total

Nov 3 - Nov 4

Total with taxes and fees

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

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

14. Palagina la cascina

Figline e Incisa Valdarno

Emma

$48 nightly

$54 total

Oct 20 - Oct 21

Total with taxes and fees

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

A building with a beige facade, multiple windows with dark shutters, and a tiled roof.

A hotel room with a large bed, a desk, a chair, a chandelier, and a view of a building through the window.

A spacious living room with yellow upholstered sofas, a glass coffee table, and a statue.

15. Hotel Rifugio la Foresta

Reggello

Gezim

$82 nightly

$95 total

Nov 17 - Nov 18

Total with taxes and fees

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.

A swimming pool with lounge chairs, a stone wall, and a building with a tiled roof.

A dining area with a glass-top table, wicker chairs, a fruit bowl, and a bottle of orange juice.

A landscaped garden with a fountain, tall cypress trees, and a brick archway.

16. Viesca Toscana Suites & Villas

Reggello

Kerby

$228 nightly

$254 total

Oct 21 - Oct 22

Total with taxes and fees

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

An outdoor dining area with stone flooring and tables, surrounded by greenery and a building with multiple balconies.

A rustic bar area with wooden beams, a long counter, and large ceramic pots.

An outdoor amphitheater with stone steps and a grassy area in front.

17. Hotel Fattoria degli Usignoli

Reggello

Brittney

$93 nightly

$110 total

Nov 17 - Nov 18

Total with taxes and fees

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

$205 nightly

$226 total

Oct 18 - Oct 19

Total with taxes and fees

A table set for breakfast with a view of a castle on a hill.

A two-story building with a stone facade, a covered patio with a metal railing, and a well-maintained garden with roses.

A bar area with a wooden counter, shelves with bottles, and a stone wall.

A restaurant with multiple tables set for dining, featuring stone arches and wooden beams.

19. Hotel Restaurant La Torricella

Poppi

Giorgio

$82 nightly

$90 total

Oct 18 - Oct 19

Total with taxes and fees

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

A stone building with a window and a light fixture.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

20. Agriturismo San Sano

Gaiole in Chianti

Glen

$68 nightly

$80 total

Nov 2 - Nov 3

Total with taxes and fees

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Top Penna Hotel Reviews

La Certosa di Pontignano

10/10 Excellent

"Absolutely amazing stay! The room was clean, large with a great view. The staff was always willing to help. Could not have asked for more. Highly recommend!"

Hotel Continentale

10/10 Excellent

"The location of this hotel is excellent!"

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Il Gentiluomo Hotel & SPA

10/10 Excellent

"It was perfect….the outside was a little run down but the inside was perfect. They had just moved and not cleaned up so that did not help the appearance."

Borgo Del Cabreo

10/10 Excellent

"Great hotel with an amazing atmosphere and one of the best restaurants I’ve ever visited. The food was absolutely exceptional — a truly memorable experience. Highly recommended!"

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Villa Le Barone

10/10 Excellent

"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Villa Pitiana

10/10 Excellent

"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."

More cheap stays in Penna

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

$46 nightly

$54 total

Oct 20 - Oct 21

Total with taxes and fees

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

$152 nightly

$172 total

Nov 3 - Nov 4

Total with taxes and fees

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

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Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

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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

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Frequently asked questions

What is the best area to stay in Penna?

The best area to stay in Penna, Tuscany, is directly within the historic center of Penna, or in the surrounding countryside just outside the town walls.The historic center of Penna is ideal for those who appreciate being within walking distance of local life. You'll find yourself amidst narrow cobblestone streets, traditional Tuscan architecture, and local shops and eateries. The main piazza, Piazza Amerighi, serves as a central gathering point, often hosting local markets. This area is particularly well-suited for solo travelers or couples who enjoy exploring on foot and experiencing the town's daily rhythms.For those seeking a more tranquil experience with scenic views, the countryside immediately surrounding Penna offers excellent options. Here, you'll find villas and farmhouses located among olive groves and vineyards, often boasting amenities like private pools and expansive gardens.

When is the best time to go to Penna?

The best times to go to Penna, Tuscany, are during the shoulder seasons of April to May and September to October. These periods offer pleasant weather, fewer crowds, and the best opportunities to experience the region's culinary and scenic highlights.For those interested in exploring the Tuscan countryside, late spring (April-May) is ideal. The landscapes are lush and green, wildflowers are in bloom, and the temperatures are comfortable for outdoor activities like hiking or vineyard tours. It's also a wonderful time to enjoy al fresco dining as the days grow longer.Couples looking for a romantic getaway will find early autumn (September-October) perfect. The grape harvest season brings a special vibrancy to the vineyards, and the changing foliage creates stunning backdrops for scenic drives.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Penna.

How much is the nightly rate at a Penna hotel?

Prices for hotels in Penna often vary, but you can find a great deal from $54 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Find hotels in Penna from $54

Upfront pricing

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 Valdarno

3. Villa Casagrande Resort & SPA

4. Hotel Il Viandante

5. Boutique Hotel Fox's Inn

6. Delta Hotel

7. Villa Barberino

8. Hotel Michelangelo

9. Hotel Toscana

10. Hotel Tenuta Il Burchio

11. Casale La Gora

12. Chapter Chianti, a Member of Design Hotels

13. Villa Rigacci

14. Palagina la cascina

15. Hotel Rifugio la Foresta

16. Viesca Toscana Suites & Villas

17. Hotel Fattoria degli Usignoli

18. Villa Sassolini Country Boutique Hotel

19. Hotel Restaurant La Torricella

20. Agriturismo San Sano

Top Penna Hotel Reviews

La Certosa di Pontignano

Hotel Continentale

Castello di Spaltenna- Small Luxury Hotels of the World

Il Gentiluomo Hotel & SPA

Borgo Del Cabreo

Borgo Vescine

Villa Le Barone

Hu Norcenni Girasole Village

Villa Pitiana

More cheap stays in Penna

Hotel Chenno

Castello di Bossi

Villa Norcenni Aparthotel

Castello di Pratelli

Agriturismo I Bonsi

Tenuta La Pieve Casale Presciano

Frequently asked questions

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