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Find hotels in Penna from $56

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Our top choices for Penna hotels

A person pouring a liquid from a bottle into a glass.
A modern building with a glass facade, a car parked in front, and a well-lit entrance area.
A glass table with a sandwich and a drink, a yellow sofa, and a fireplace with flames.
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.

1. Moody smart & comfy Hotel

Moody smart & comfy Hotel
Terranuova Bracciolini
Italy
Maurizio
$111 nightly
$126 total
Oct 2 - Oct 3
Total with taxes and fees
Moody smart & comfy Hotel
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 modern hotel lobby with a curved reception desk, seating area, and a bar.

2. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
$109 nightly
$120 total
Oct 2 - Oct 3
Total with taxes and fees
Hotel Valdarno
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 dining area with a table set for breakfast, featuring plates, cutlery, and a pitcher of juice.

3. Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
United States
Shannon
$119 nightly
$131 total
Oct 2 - Oct 3
Total with taxes and fees
Dimora Casa Eugenia
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 covered outdoor seating area with wicker furniture and a potted plant.
A modern lobby with a reception desk, two seating areas with orange chairs, and a marble floor.

4. Hotel Il Viandante

Hotel Il Viandante
Terranuova Bracciolini
United States
Michelle
$113 nightly
$130 total
Sep 8 - Sep 9
Total with taxes and fees
Hotel Il Viandante
A hotel room with a bed, a desk with a laptop, a chair, a nightstand, and a view through the window.
A hotel with a sign reading "Michelangelo HOTEL".
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.

5. Hotel Michelangelo

Hotel Michelangelo
Terranuova Bracciolini
United States
Sushil
$103 nightly
$117 total
Oct 1 - Oct 2
Total with taxes and fees
Hotel Michelangelo
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 hotel room with a bed, a TV, a desk, and a mirror.

6. Delta Hotel

Delta Hotel
Montevarchi
United States
weixing
$109 nightly
$120 total
Oct 2 - Oct 3
Total with taxes and fees
Delta Hotel
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 historic building with a stone facade, arched entrance, and a wooden balcony.
An indoor swimming pool with clear glass walls, wooden beams, and large windows.

7. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Jason
$165 nightly
$184 total
Sep 27 - Sep 28
Total with taxes and fees
Villa Casagrande Resort & SPA
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 room with a large window offering a view of a vineyard and distant hills.
A stone building with a large wooden door and arched entrance, flanked by potted plants.

8. Palagina la Dimora

Palagina la Dimora
Figline e Incisa Valdarno
Canada
Tarek
$68 nightly
$77 total
Sep 13 - Sep 14
Total with taxes and fees
Palagina la Dimora
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.

9. Boutique Hotel Fox's Inn

Boutique Hotel Fox's Inn
San Giustino Valdarno
$105 nightly
$115 total
Sep 30 - Oct 1
Total with taxes and fees
Boutique Hotel Fox's Inn
A stone building with outdoor seating and a pool in the background.
A stone house with a paved driveway and a lawn, surrounded by trees and a white car parked in front.
A bedroom with two beds, a chandelier, a leopard-print chair, and a small table with a vase.
A dining table set with various foods, including meats, cheeses, and fruits.

10. B&B Country House Poggio del Drago

B&B Country House Poggio del Drago
Civitella in Val di Chiana
United States
Kristen
$105 nightly
$116 total
Sep 6 - Sep 7
Total with taxes and fees
B&B Country House Poggio del Drago
A pool with lounge chairs and umbrellas, surrounded by a vineyard and mountains in the background.
An outdoor dining area with wooden tables and chairs, surrounded by greenery and stone walls.
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.

11. Borgo Iesolana Country Retreat

Borgo Iesolana Country Retreat
Bucine
Italy
costanza
$220 nightly
$247 total
Sep 7 - Sep 8
Total with taxes and fees
Borgo Iesolana Country Retreat
An outdoor dining area with multiple tables and umbrellas, surrounded by greenery and hills in the background.
A modern bedroom with a large bed, a wooden headboard, a built-in bathtub, and a stone wall.
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.

12. Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
United States
Peter
$75 nightly
$84 total
Sep 3 - Sep 4
Total with taxes and fees
Palagina la cascina
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.
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.

13. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
United Kingdom
Peter
$267 nightly
$294 total
Oct 1 - Oct 2
Total with taxes and fees
Villa Sassolini Country Boutique Hotel
A dining table set up outdoors with a view of a landscape.
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.
A villa with a swimming pool surrounded by lush greenery and hills in the background.

14. Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
United States
Nichole
$699 nightly
$769 total
Sep 20 - Sep 21
Total with taxes and fees
Il Borro - Relais & Châteaux
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
A modern living room with a white sofa, armchairs, and a coffee table.
An aerial view of a rural village with traditional buildings, a swimming pool, and terraced fields.

15. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
$394 nightly
$440 total
Sep 17 - Sep 18
Total with taxes and fees
Chapter Chianti, a Member of Design Hotels
A traditional stone building with a garden featuring geometric hedges and potted plants.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A view of a garden with neatly trimmed hedges and a central water feature.

16. Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
United States
Thomas
$214 nightly
$244 total
Sep 7 - Sep 8
Total with taxes and fees
Badia a Coltibuono
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 bedroom with a bed, a window with curtains, a lamp, and a patterned wall.
A swimming pool with lounge chairs, a stone wall, and a building with a tiled roof.
A landscaped garden with a fountain, tall cypress trees, and a brick archway.

17. Viesca Toscana Suites & Villas

Viesca Toscana Suites & Villas
Reggello
United States
Jessica
$349 nightly
$387 total
Sep 29 - Sep 30
Total with taxes and fees
Viesca Toscana Suites & Villas
An outdoor patio area with a brick archway, potted plants, and wicker furniture.
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.
A swimming pool with steps leading into it, surrounded by lounge chairs and a stone wall with greenery.

18. Hotel Tenuta Il Burchio

Hotel Tenuta Il Burchio
Figline e Incisa Valdarno
Netherlands
OY
$88 nightly
$98 total
Sep 9 - Sep 10
Total with taxes and fees
Hotel Tenuta Il Burchio
A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.
An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.
A poolside area with a swimming pool, lounge chairs, and a grassy lawn.
A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.

19. Il Verreno

Il Verreno
Ambra
Canada
Minna
$275 nightly
$307 total
Sep 5 - Sep 6
Total with taxes and fees
Il Verreno
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone house with a tiled roof, surrounded by greenery and a gravel path.
A stone building with a balcony, potted plants, and a view of distant hills.
A stone-walled room with a sofa, a coat rack, and a window with curtains.

20. Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
$416 nightly
$463 total
Sep 23 - Sep 24
Total with taxes and fees
Podere L'Aquila
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Top Penna Hotel Reviews

Borgo Scopeto Wine & Country Relais

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!"
Hannah 3-night trip
Posted 1 hour ago
Borgo Scopeto Wine & Country Relais
Belvedere di San Leonino

Belvedere di San Leonino

10/10 Excellent
"Staff is great. Room clean. Property beautiful and dinner was delicious"
Seong Won 1-night trip
Posted 3 hours ago
Belvedere di San Leonino
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Beautiful place, very quiet, in love with gardens"
Malena 1-night trip
Posted 1 day ago
La Certosa di Pontignano
Villa Pitiana

Villa Pitiana

10/10 Excellent
"Lovely room and gorgeous location. Best to have a car when coming as it is far away from major areas. Lots of in-house facilities and walks. Good for a relaxing break. We enjoyed family holiday, with visits to the pool and easy drive to Florence."
Rahul 2-night trip
Posted 4 days ago
Villa Pitiana
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"Staff was incredibly friendly, rooms very clean and were cleaned every day, and the property is amazing! The restaurant had such great food with a nice atmosphere as well! Highly recommend staying here!"
Eric 5-night trip
Posted 8 days ago
Castello Vicchiomaggio
Palagina la Dimora

Palagina la Dimora

10/10 Excellent
"Beautiful to stay in the main house. The breakfasts were great to start the day - really enjoyed sitting around the pool, nice and peaceful with amazing view. Rooms were comfortable. Easy to get out and try local restaurants and visit other places. Only think for us is it could do with a gym - if you're onsite all day, this would have just made the place perfect."
Mark 5-night trip
Posted 9 days ago
Palagina la Dimora
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."
Natasha 4-night trip
Posted 9 days ago
Villa Casagrande Resort & SPA
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"This property is amazing! The views are absolutely breathtaking, and the food is delicious. I highly recommend it. It’s also a fantastic choice for families, as the staff are incredibly accommodating and welcoming toward children."
Stacey 2-night trip
Posted 10 days ago
Hotel Villa Campomaggio
Hotel Fattoria degli Usignoli

Hotel Fattoria degli Usignoli

10/10 Excellent
"Gorgeous place, amazing views. They overbooked dinner and we had a wait of 2 hours for our food to come out. Pool was amazing and there was two to choose from, one looked quieter. Main part of the building is 15th century, which was beautiful. Easy to find with google maps NOT Apple Maps. Plenty of parking."
Ant 1-night trip
Posted 3 weeks ago
Hotel Fattoria degli Usignoli

More cheap stays in Penna

Hotel Chenno

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR
$47 nightly
$56 total
Sep 2 - Sep 3
Total with taxes and fees
Hotel Chenno
Villa Norcenni Aparthotel

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI
$112 nightly
$125 total
Sep 2 - Sep 3
Total with taxes and fees
Villa Norcenni Aparthotel
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
$177 nightly
$200 total
Sep 3 - Sep 4
Total with taxes and fees
Castello di Bossi
Castello di Pratelli

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI
Get rates
9.2/10 Wonderful! (5 reviews)
Castello di Pratelli
Agriturismo I Bonsi

Agriturismo I Bonsi

VIA BONSI Reggello FI
Get ratesAgriturismo I Bonsi
Tenuta La Pieve Casale Presciano

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR
Get ratesTenuta La Pieve Casale Presciano

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 $56 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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