Penna Hotel & Accommodation Deals 2026 from AU$78 - Compare prices by date

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Penna

Pet friendly

Apartment

Villa

Apart hotel

Spa

Pool

Condo

Spa pool

Cottage

Family friendly

Farm

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Penna hotels

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

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

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

A modern building with a glass facade, a car parked in front, and a well-lit entrance area.

1. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

AU$182

includes taxes & fees

4 Oct - 5 Oct

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 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.

2. Hotel Il Viandante

Terranuova Bracciolini

Michelle

AU$166

includes taxes & fees

18 Oct - 19 Oct

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

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

A hotel hallway with a polished floor, wooden doors, and a green exit sign.

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

3. Hotel Michelangelo

Terranuova Bracciolini

Sushil

AU$164

includes taxes & fees

1 Oct - 2 Oct

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

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

A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.

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

4. Hotel Valdarno

Montevarchi

Emmanuel

AU$190

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

5. Delta Hotel

Montevarchi

weixing

AU$180

includes taxes & fees

9 Oct - 10 Oct

A stone building with a brick facade, a well-maintained lawn, and a pathway leading to the entrance.

A patio with green metal chairs and tables, a white building with large windows, and a view of a hill with greenery and a house in the distance.

A rustic kitchen with wooden cabinets, a dining table set for two, and a sofa in a cozy corner.

A pool with clear blue water, surrounded by white lounge chairs and umbrellas, with a view of distant mountains.

6. Agriturismo Antico Borgo Poggitazzi

Terranuova Bracciolini

Michael

AU$174

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

7. Boutique Hotel Fox's Inn

San Giustino Valdarno

AU$130

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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

8. Villa Barberino

Meleto

Claire

AU$207

includes taxes & fees

26 Oct - 27 Oct

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

A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

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.

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

9. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

AU$344

includes taxes & fees

1 Oct - 2 Oct

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.

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

10. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

AU$185

includes taxes & fees

29 Oct - 30 Oct

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

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

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

A reception area with a wooden ceiling, a reception desk, and seating.

11. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

AU$438

includes taxes & fees

6 Oct - 7 Oct

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone archway leading to a window with a view of tall trees and a distant landscape.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

12. Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

AU$238

includes taxes & fees

29 Oct - 30 Oct

A swimming pool with a view of a historic building surrounded by olive trees.

An outdoor café with tables and chairs, surrounded by stone walls and greenery.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

13. Castello di Meleto

Gaiole in Chianti

Vinesh

AU$257

includes taxes & fees

29 Sept - 30 Sept

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

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

A bedroom with a bed, a window with curtains, a lamp, and a patterned wall.

14. Viesca Toscana Suites & Villas

Reggello

Kerby

AU$332

includes taxes & fees

17 Oct - 18 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 villa with a swimming pool surrounded by lush greenery and hills in the background.

15. Il Borro - Relais & Châteaux

Loro Ciuffenna

Nichole

AU$954

includes taxes & fees

14 Oct - 15 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 swimming pool with a breakfast tray of fruits and juice, surrounded by trees and a clear sky.

16. B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

AU$166

includes taxes & fees

4 Oct - 5 Oct

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

An outdoor courtyard with stone walls, potted plants, and a wooden door leading to an interior space.

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

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

17. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

AU$134

includes taxes & fees

6 Oct - 7 Oct

A stone building with multiple windows and a central entrance.

A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.

A dining area with a table set for two, white chairs, and a stone-patterned floor.

A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.

18. Fondaco del Moro

Civitella in Val di Chiana

Heather

AU$109

includes taxes & fees

29 Sept - 30 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.

An outdoor dining area with wooden tables and chairs, surrounded by greenery and stone walls.

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

19. Borgo Iesolana Country Retreat

Bucine

MvE

AU$292

includes taxes & fees

22 Oct - 23 Oct

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

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

A poolside area with lounge chairs and a swimming pool.

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

20. Casale La Gora

Figline e Incisa Valdarno

Caleb

AU$158

includes taxes & fees

28 Oct - 29 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Penna Hotel Reviews

Recent Reviews in Penna

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."

Borgo Scopeto Wine & Country Relais

8/10 Good

"Staff are nice!"

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."

Belvedere di San Leonino

10/10 Excellent

"This hotel is a beautiful romantic getaway. You will relax and take in the lovely Chianti Classico scenery at the pool. At night the restaurant prepared delicious local cuisine and you can pair it with an amazing bottle of local wine!"

La Certosa di Pontignano

10/10 Excellent

"Everything about this property is wonderful from the lodging to the staff!"

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."

Villa Il Palagio

10/10 Excellent

"The check in went great and the property is amazingly managed, a beautiful villa in the hills of Tuscany. It felt magic just walking to it, I would absolutely recommend renting a car if you want to go into Florence often."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Relais Vignale & Spa

10/10 Excellent

"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."

More cheap accommodation in Penna

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

AU$78

29 Sept - 30 Sept

includes taxes & fees

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

AU$94

30 Sept - 1 Oct

includes taxes & fees

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

AU$249

20 Oct - 21 Oct

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

Get rates

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

Get rates

Frequently asked questions

What is the best area to stay in Penna?

The best area to stay in Penna is within the historic centre of the town, particularly around Piazza della Repubblica and Corso Matteotti.This central area is the heart of Penna, offering a quintessential Tuscan experience. It's characterised by narrow, winding cobblestone streets, mediaeval architecture, and charming piazzas. You'll find a good selection of trattorias, local shops selling artisan goods, and cafes, all within a short stroll. The Duomo di Penna, a prominent landmark, is also found here.Couples looking for a romantic escape will find the historic centre particularly appealing. The evenings are pleasant for leisurely walks, enjoying aperitivos in a quiet piazza, and dining at authentic local restaurants. The convenience of having everything on your doorstep allows for a relaxed holiday without the need for constant travel.For those seeking a more secluded and tranquil experience, the hills just outside Penna's historic walls offer beautiful villa and agriturismo options. These properties often come with stunning views of the Tuscan countryside, private pools, and larger spaces.

When is the best time to go to Penna?

The best time to go to Penna, Tuscany, Italy, is during the spring (April to June) and autumn (September to October) months. These periods offer pleasant weather, ideal for exploring the region's beauty without the intense summer heat or winter chill.Spring in Penna sees the countryside burst into bloom, with comfortable temperatures ranging from 15°C to 25°C. This is an excellent time for outdoor activities such as hiking, cycling, and visiting vineyards. The olive groves and vineyards are particularly picturesque, and you'll find fewer crowds compared to the peak summer months.Autumn also provides wonderful conditions, with temperatures typically between 18°C and 28°C. The landscape takes on beautiful golden and russet hues, and it's harvest season for grapes and olives, offering unique opportunities to experience local traditions. Many food and wine festivals take place during this time, making it great for food lovers.While July and August offer warm, sunny weather, temperatures can often exceed 30°C, which can be quite hot for extensive sightseeing or outdoor activities. These months also see the highest number of visitors, meaning more crowded attractions and higher prices.

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 cancelled 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 can I save on a hotel booking in Penna with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Penna hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Penna?

Prices for hotels in Penna often vary, but you can find a great deal from AU$78 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 our cheapest rates.

Explore a world of travel with Expedia

Arezzo Holiday Rentals

Book Hotels in Penna on Expedia.it

Search Penna hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Penna

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Penna hotels

1. Moody smart & comfy Hotel

2. Hotel Il Viandante

3. Hotel Michelangelo

4. Hotel Valdarno

5. Delta Hotel

6. Agriturismo Antico Borgo Poggitazzi

7. Boutique Hotel Fox's Inn

8. Villa Barberino

9. Villa Sassolini Country Boutique Hotel

10. Villa Casagrande Resort & SPA

11. Chapter Chianti, a Member of Design Hotels

12. Castello di Tornano Wine Resort

13. Castello di Meleto

14. Viesca Toscana Suites & Villas

15. Il Borro - Relais & Châteaux

16. B&B Country House Poggio del Drago

17. Hotel Tenuta Il Burchio

18. Fondaco del Moro

19. Borgo Iesolana Country Retreat

20. Casale La Gora

Top Penna Hotel Reviews

Recent Reviews in Penna

Villa Le Barone

Borgo Scopeto Wine & Country Relais

Hu Norcenni Girasole Village

Belvedere di San Leonino

La Certosa di Pontignano

Villa Pitiana

Villa Il Palagio

Hotel Villa Campomaggio

Relais Vignale & Spa

More cheap accommodation in Penna

Hotel Chenno

Villa Norcenni Aparthotel

Castello di Bossi

Castello di Pratelli

Agriturismo I Bonsi

Tenuta La Pieve Casale Presciano

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app