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Our top choices for Bossi hotels

Castello di Bossi

Castello di Bossi
2.0 star property
Castelnuovo Berardenga
7.8 out of 10, Good, (8 reviews)
"The location is great if you get to the hotel in a car. "
Mexico
CESAR JAVIER
The price is CA $174
CA $327 total
includes taxes & fees
Jul 14 - Jul 15
Castello di Bossi

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
5.0 star property
Cavriglia
The price is CA $472
CA $529 total
includes taxes & fees
Jul 25 - Jul 26
Chapter Chianti, a Member of Design Hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (546 reviews)
"Amazing property, loved staying there. Huge rooms, AC worked well, beautiful setting. It’s well worth your time to stay there"
United States
Ken
The price is CA $204
CA $237 total
includes taxes & fees
Jul 11 - Jul 12
La Certosa di Pontignano

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (45 reviews)
"One of our favorite stays in Italy! Few number of rooms which makes it feel very relaxing and comfortable. Staff was friendly and helpful."
Canada
Yael
The price is CA $165
CA $190 total
includes taxes & fees
Jul 15 - Jul 16
Hotel Ristorante La Dama nella Vigna

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (396 reviews)
"The hotel is beautiful."
United States
Ruth
The price is CA $247
CA $272 total
includes taxes & fees
Jul 12 - Jul 13
Castello Vicchiomaggio

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (60 reviews)
"A little far away from Siena, but buses came by regularly and taxi's only cost about 12 Euros to get you to and from Siena."
United States
Jack
The price is CA $117
CA $137 total
includes taxes & fees
Jul 10 - Jul 11
Palace Hotel Due Ponti

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (75 reviews)
"This hotel was fantastic! A gem, off the beaten path. Plenty of space and quiet accompanied by crisp fresh air. The restaurant in the hotel lobby was delicious and affordable. I hope to return here."
United States
Martin
The price is CA $111
CA $129 total
includes taxes & fees
Jul 19 - Jul 20
Castello

Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
9.6 out of 10, Exceptional, (79 reviews)
"Whole place felt amazing, staff was super! Def recommend!"
United States
Roberto Javier Sanz
The price is CA $289
CA $326 total
includes taxes & fees
Jul 31 - Aug 1
Relais la Costa - Dimora Storica

Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
10.0 out of 10, Exceptional, (97 reviews)
"This place is amazing. Wonderful drive to the hotel and the solitude is so great. The breakfast was amazing. Staff was very friendly for our stay. Definitely go back."
Canada
Shawn
The price is CA $136
CA $156 total
includes taxes & fees
Jul 8 - Jul 9
Agriturismo San Sano

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (216 reviews)
"Great Toscana hotel"
United States
Jose
The price is CA $260
CA $292 total
includes taxes & fees
Aug 7 - Aug 8
Villa Sabolini

Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (186 reviews)
"Very clean and amazing staff. And the room is at such a nice and rich location with a beautiful view."
United States
Christopher
The price is CA $191
CA $220 total
includes taxes & fees
Jul 10 - Jul 11
Belvedere di San Leonino

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
9.8 out of 10, Exceptional, (8 reviews)
"This property has been under renovation for the past few years, with about another year of construction still to go. They are transforming an old winery into what will eventually be a 5- or 6-star resort, complete with a spa and other amenities. We stayed for two nights with our 11- and 13-year-olds and booked a family suite. The master bedroom bed was extremely comfortable, and the kids’ fold-out bed was large and surprisingly comfortable as well. The bathroom was brand new and had a door...
United States
Brian
The price is CA $452
CA $507 total
includes taxes & fees
Aug 7 - Aug 8
Fattoria di Vegi

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast options, amazing views, peaceful atmosphere, great lunch and dinner, and of course amazing wine."
United States
Austin
The price is CA $339
CA $386 total
includes taxes & fees
Aug 5 - Aug 6
Castello di Tornano Wine Resort

Palagina la cascina

Palagina la cascina
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (124 reviews)
"Amazing hotel with beautiful territory"
United States
Igor
The price is CA $115
CA $129 total
includes taxes & fees
Jul 10 - Jul 11
Palagina la cascina

Castello La Leccia

Castello La Leccia
Castellina in Chianti
10.0 out of 10, Exceptional, (112 reviews)
"Amazing property with great staff."
United States
Samuel
The price is CA $384
CA $429 total
includes taxes & fees
Jul 15 - Jul 16
Castello La Leccia

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (133 reviews)
"Really enjoyed our stay, clean room and property. Very quiet place with a nice pool."
Canada
Meghan
The price is CA $290
CA $328 total
includes taxes & fees
Jul 9 - Jul 10
Castello di Leonina Relais

Palazzo di Valli

Palazzo di Valli
3.0 star property
Siena
9.6 out of 10, Exceptional, (424 reviews)
"We had a blast, and the proprietors were fantastic. They had plenty of local knowledge and seemed to have a real passion for what they do. Plus the venue is wonderful, and they have the best patio with views of the Tuscan hills. Would recommend, and would stay again."
United States
John
The price is CA $153
CA $177 total
includes taxes & fees
Jul 12 - Jul 13
Palazzo di Valli

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (198 reviews)
"Beautiful property and very friendly helpful staff"
Canada
Pamela
The price is CA $475
CA $535 total
includes taxes & fees
Jul 15 - Jul 16
Dievole Wine Resort

Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (222 reviews)
"Incredible place to stay in the Chianti region. Beautiful grounds, amazing food, clean and comfortable rooms, and incredible staff. Location was perfect too! "
United States
Alex
The price is CA $87
CA $122 total
includes taxes & fees
Jul 12 - Jul 13
Hotel Casafrassi

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (217 reviews)
"Very peaceful and staff was very helpful with reservations for excursions"
United States
Giancarlo
The price is CA $220
CA $249 total
includes taxes & fees
Jul 8 - Jul 9
Castello di Fonterutoli Wine Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bossi Hotel Reviews

More cheap stays in Bossi

Frequently asked questions

What is the best area to stay in Bossi?
The best area to stay in Bossi is within the historic centre of Bossi itself, or in one of the beautiful agriturismi or villas scattered across the surrounding Tuscan countryside.

The historic centre of Bossi is great for those who appreciate being able to walk to everything. It's a compact area with narrow, winding streets, historic buildings, and a central piazza where you'll find local shops, cafes, and trattorias. Staying here means you're right in the heart of local life and can easily enjoy an evening stroll after dinner. This is a great choice for couples who want to experience the local culture and have amenities on their doorstep.

For those seeking a more secluded and luxurious experience, the surrounding countryside offers numerous agriturismi and private villas. These properties often boast stunning views of rolling vineyards and olive groves, private swimming pools, and high-end amenities. They provide a tranquil retreat, ideal for families or couples looking for a peaceful escape with plenty of space and privacy. Many also offer cooking classes or wine tasting experiences right on site.
When is the best time to go to Bossi?
The best time to visit Bossi, Tuscany, is during the shoulder seasons of May, June, September, and early October.

These months offer pleasant weather, with warm days superb for exploring the countryside and enjoying outdoor activities without the intense heat or larger crowds of the peak summer months. You'll find the vineyards lush and the light ideal for photography.

Couples often find these times superb for a romantic getaway. The weather is comfortable for leisurely walks through olive groves, wine tastings at local vineyards, and dining al fresco at a trattoria. You can enjoy the scenery and local culture at a relaxed pace.

For travellers interested in culinary experiences and local festivals, September and October are particularly appealing.
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 Bossi.
How can I save on a Bossi hotel booking with Expedia?
Members always get our best prices. Find our best Bossi hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Bossi hotel?
Prices for hotels in Bossi often vary, but you can find a great deal from CA $112 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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