Penna Hotels from S$67

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Top 10 trending Penna hotels

Castello Vicchiomaggio

9.4 out of 10, Exceptional, (355)
"This property is gorgeous! The grounds are beautiful. The restaurant was excellent! "
The price is S$294
includes taxes & fees
22 Sept - 23 Sept
Castello Vicchiomaggio

Agriturismo San Sano

3.0 star property
10.0 out of 10, Exceptional, (63)
"Great place to stay in Chianti region, quiet and charming property."
Agriturismo San Sano

La Certosa di Pontignano

9.6 out of 10, Exceptional, (459)
"Excellent staff, great food. "
The price is S$213
includes taxes & fees
1 Sept - 2 Sept
La Certosa di Pontignano

Casa Ruffino

9.8 out of 10, Exceptional, (8)
"The best stay of my life "
Casa Ruffino

Palazzo Squarcialupi

4.0 star property
9.8 out of 10, Exceptional, (62)
"This was hands down the most spectacular vacation spot we could have asked for while travelling around Chianti. The staff are so helpful and friendly and the hotel itself is spotless and very comfortable. We hope to come back and bring many more family members with us! Thank you for such a great stay!! "
The price is S$296
includes taxes & fees
21 Sept - 22 Sept
Palazzo Squarcialupi

Albergo Villa San Michele

10.0 out of 10, Exceptional, (1)
"Amazing hosts, amazing location and amazing food. So glad we had the opportunity to stay with Alice and Daniele and would stay again in a heartbeat. Super dog friendly even with our silly pup. The breakfast and restaurant are top notch."
The price is S$152
includes taxes & fees
28 Aug - 29 Aug
Albergo Villa San Michele

La pietra del cabreo

10.0 out of 10, Exceptional, (87)
"Place is awesome "
La pietra del cabreo

Relais Vignale & Spa

4.0 star property
9.2 out of 10, Wonderful, (275)
"My friend and I had such a relaxing time at Relais!! We both got amazing massages from Natalie, the staff helped me figure out how to get to Rome after, the rooms were GORGEOUS, the pool was spectacular and got great poolside drinks, and the food/wine was the best!!! Stay here for a romantic and relaxing getaway surrounded by Tuscany’s beautiful rolling hills and vineyards. Would definitely come back!"
The price is S$298
includes taxes & fees
31 Aug - 1 Sept
Relais Vignale & Spa

Albergo Del Chianti

3.0 star property
8.6 out of 10, Excellent, (178)
"Such a beautiful place to stay on the square. Walking trails are literally in the doorstep, dining options are plentiful and the staff were so friendly and helpful. "
Albergo Del Chianti

Borgo Scopeto Wine & Country Relais

5.0 star property
9.2 out of 10, Wonderful, (182)
"Great location, great views, the entire staff was amazing. Truly a perfect place. "
Borgo Scopeto Wine & Country Relais

Villa Rigacci

4.0 star property
9.4 out of 10, Exceptional, (45)
"Awesome place, peaceful quiet great food. Staff was always very helpful. "
The price is S$236
includes taxes & fees
1 Sept - 2 Sept
Villa Rigacci

Borgo I Tre Baroni

4.0 star property
9.2 out of 10, Wonderful, (81)
"Amazing place very picturesque definitely would recommend "
Borgo I Tre Baroni

Villa Le Barone

4.0 star property
9.4 out of 10, Exceptional, (133)
"A lovely retreat - quiet and serene. The grounds of the villa are amazing and all of the staff are lovely. Panzano is a short and scenic 20 minute walk away. We wish we could have stayed longer! "
The price is S$311
includes taxes & fees
23 Sept - 24 Sept
Villa Le Barone

Castello La Leccia

10.0 out of 10, Exceptional, (78)
"The most wonderful place to stay! "
The price is S$441
includes taxes & fees
30 Aug - 31 Aug
Castello La Leccia

Agriturismo Cuprena

9.4 out of 10, Exceptional, (15)
"Beautiful property, friendly and helpful staff. Breakfast adequate but not special. Restaurant staff friendly and helpful but food a bit pretentious and overpriced."
The price is S$436
includes taxes & fees
23 Sept - 24 Sept
Agriturismo Cuprena

Locanda Il Gallo

3.0 star property
9.4 out of 10, Exceptional, (50)
"The property owner was very helpful explaining wineries location and local food! The in-house restaurant was excellent and convenient! "
The price is S$202
includes taxes & fees
28 Aug - 29 Aug
Locanda Il Gallo

Hotel Croce di Savoia

3.0 star property
8.2 out of 10, Very good, (16)
"Ok"
Hotel Croce di Savoia

Pieve Aldina - Fontenille Collection

5.0 star property
10.0 out of 10, Exceptional, (23)
"Lovely stay "
Pieve Aldina - Fontenille Collection

I Salici Agriturismo

9.6 out of 10, Exceptional, (4)
"We had an amazing stay at this property. The pictures do not do it justice - it is tremendously beautiful. Marco and team were warm, welcoming and incredibly generous. Thank you for an unforgettable stay. We will be back!"
The price is S$197
includes taxes & fees
7 Sept - 8 Sept
I Salici Agriturismo

Castello di Fonterutoli Wine Resort

9.4 out of 10, Exceptional, (181)
"The best place to stay . I loved it "
The price is S$267
includes taxes & fees
31 Aug - 1 Sept
Castello di Fonterutoli Wine Resort
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Frequently asked questions

Where is the best place to stay in Penna?

Castello di Spaltenna- Small Luxury Hotels of the World, located 11.4 mi (18.4 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 Borgo Scopeto Wine & Country Relais and A Point Arezzo Park Hotel. 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 electric kettle. 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?

Castello di Spaltenna- Small Luxury Hotels of the World: Features an indoor pool, an outdoor pool and 2 restaurants. Borgo Scopeto Wine & Country Relais and A Point Arezzo Park Hotel 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 8 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 San Pietro a Gropina, Croce del Pratomagno and Le Miccine. You'll also find Badia a Coltibuono and Castello di Albola 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.