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Our top choices for Bossi hotels

A courtyard with stone walls, arched windows, and potted plants.
An outdoor courtyard with stone walls, arched windows, and potted plants.
A covered outdoor area with brick arches, potted plants, and a door leading to a building.
A rustic interior with a stone wall, a wooden staircase, and a view of the outdoors.

1. Castello di Bossi

Castello di Bossi
Castelnuovo Berardenga
Mexico
CESAR JAVIER
￥11,440
￥27,389 total
includes taxes & fees
Oct 20 - Oct 21
Castello di Bossi
A building with a stone facade, a central arched doorway, and a window with a decorative frame.
A room with a glass table, a vase with flowers, a bottle of wine, and a chair.
A room with a view of a forest through a window, a table with a lamp, and a chair.
A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

2. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
Canada
Marissa
￥42,365
￥48,028 total
includes taxes & fees
Oct 28 - Oct 29
Dievole Wine Resort
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A table set for breakfast with various dishes, drinks, and a newspaper.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

3. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
￥76,850
￥86,319 total
includes taxes & fees
Oct 21 - Oct 22
Hotel Le Fontanelle
A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.
A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.
A modern living room with a glass coffee table, white sofas, and decorative plants.
An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.

4. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Susan
￥12,624
￥14,420 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Executive
A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.
An interior corridor with arches, columns, and a brick wall.

5. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Leslie
￥13,779
￥16,579 total
includes taxes & fees
Nov 2 - Nov 3
La Certosa di Pontignano
A terrace with multiple sun loungers and a scenic view of green fields and hills.
A spa room with a reception desk, a massage chair, and a window with blinds.
A spacious living area with a wooden coffee table, a large potted plant, and a sofa.
A modern hotel room with a bed, a small table with a hat, a red chair, a window with curtains, and a bathroom with a glass shower enclosure.

6. Precise House Montaperti Siena

Precise House Montaperti Siena
Asciano
Canada
Dieter
￥13,072
￥15,445 total
includes taxes & fees
Nov 2 - Nov 3
Precise House Montaperti Siena
A historic stone building with multiple windows and a courtyard.
A stone building with outdoor seating and a garden with roses.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.
A pool area with lounge chairs and a service person attending to a guest.

7. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
￥110,104
￥122,899 total
includes taxes & fees
Oct 25 - Oct 26
Borgo San Felice Resort
A large building with multiple rooms, surrounded by a field of lavender.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.
An arched brick corridor leading to a dining area with tables set for a meal.

8. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
Canada
GUANGMIN
￥60,474
￥68,299 total
includes taxes & fees
Nov 2 - Nov 3
Borgo Scopeto Wine & Country Relais
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A stone building with a garden, tall trees, and a clear blue sky.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

9. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
￥52,537
￥59,574 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.
A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.
A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.
A bathroom with a sink, mirror, and shower.

10. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Linda
￥14,012
￥15,946 total
includes taxes & fees
Nov 2 - Nov 3
Sangallo Park Hotel
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

11. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
￥54,582
￥61,824 total
includes taxes & fees
Nov 1 - Nov 2
The Club House
A courtyard with a lemon tree, potted plants, and a building with arched windows.
A swimming pool surrounded by lush greenery and a stone pathway.
A large, historic building with a covered patio and a well-maintained garden.
A room with a large window offering a view of a landscaped garden with trees and a pathway.

12. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
United Kingdom
Nigel
￥26,886
￥30,467 total
includes taxes & fees
Oct 30 - Oct 31
Villa Scacciapensieri Boutique Hotel
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
A stone building with a tower, surrounded by people dining at tables with candles.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.

13. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Lisa
￥22,407
￥26,069 total
includes taxes & fees
Oct 29 - Oct 30
Castello di Tornano Wine Resort
A modern building with a sign reading "Palace Hotel."
A buffet setup with various food items including yogurt cups, fruits, and a bowl of grapes.
A modern building entrance with a glass door reflecting a parking lot and trees.
Room

14. Palace Hotel Due Ponti

Palace Hotel Due Ponti
Due Ponti
United States
Adam
￥12,405
￥14,180 total
includes taxes & fees
Nov 1 - Nov 2
Palace Hotel Due Ponti
A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.
A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

15. Four Points by Sheraton Siena

Four Points by Sheraton Siena
Scacciapensieri
United States
Ralph
￥21,954
￥24,683 total
includes taxes & fees
Nov 2 - Nov 3
Four Points by Sheraton Siena
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 stone building with a wooden door, outdoor seating, and a pergola with vines.

16. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
￥10,960
￥12,767 total
includes taxes & fees
Nov 2 - Nov 3
Agriturismo San Sano
A table set for dining with a scenic view of rolling hills and distant mountains.
A brick building with a large arched entrance, a metal gate, and a wooden door.
A spacious dining area with round tables and wicker chairs, a patterned rug, and a wooden ceiling.
An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

17. Castello di Leonina Relais

Castello di Leonina Relais
Asciano
Canada
Meghan
￥19,905
￥22,965 total
includes taxes & fees
Oct 19 - Oct 20
Castello di Leonina Relais
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.
An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

18. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
Canada
Samantha
￥14,831
￥17,741 total
includes taxes & fees
Oct 22 - Oct 23
Ultimo Mulino Wellness Country Hotel
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A reception area with a wooden ceiling, a reception desk, and seating.
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.

19. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
￥42,648
￥47,979 total
includes taxes & fees
Oct 14 - Oct 15
Chapter Chianti, a Member of Design Hotels
A swimming pool with lounge chairs and a person in a patterned dress.
A stone staircase with candles and a sign reading "CANTINA".
An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.

20. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
￥79,710
￥89,458 total
includes taxes & fees
Nov 2 - Nov 3
Castel Monastero - The Leading Hotels of the World
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Top Bossi Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful stay."
Niel 2-night trip
Posted 7 hours ago
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Borgo San Luigi

Hotel Borgo San Luigi

8/10 Good
"Great breakfast and clean room. However, not a very kid friendly with no high chair available in the room and the few ones in the restaurant were broken or dirty. Good place for adulte."
Samuel 2-night trip
Posted 8 hours ago
Hotel Borgo San Luigi
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"A peaceful luxurious stay with amazing amenities, 6 star service & and amazing dinner restaurant."
Scott 4-night trip
Posted 8 hours ago
Borgo Scopeto Wine & Country Relais
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."
Elizabeth 1-night trip
Posted 1 day ago
Fattoria di Vegi
Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."
Michele 2-night trip
Posted 2 days ago
Hotel Athena
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 2 days ago
La Certosa di Pontignano
Hotel Minerva

Hotel Minerva

10/10 Excellent
"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."
Michael 1-night trip
Posted 4 days ago
Hotel Minerva
Hu Norcenni Girasole Village

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."
Maya 4-night trip
Posted 4 days ago
Hu Norcenni Girasole Village
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."
Reid 2-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione

More cheap stays in Bossi

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
￥8,627
￥10,023 total
Nov 2 - Nov 3
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
￥15,140
￥17,187 total
Nov 2 - Nov 3
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
￥17,513
￥20,156 total
Oct 5 - Oct 6
includes taxes & fees
7.8/10 Good! (442 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
￥19,674
￥22,174 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
￥11,440
￥27,389 total
Oct 20 - Oct 21
includes taxes & fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

Frequently asked questions

Where is the best place to stay in Bossi?
Hotel Athena, located 7.4 mi (12 km) from the heart of Bossi, is a top choice for your stay based on our traveler data. Two other options for your trip to the area are La Certosa di Pontignano and Grand Hotel Continental Siena – Starhotels Collezione. See all available top hotels, or vacation rentals in Bossi.
What are some of the best vacation rentals in Bossi?
Borgo Argiano: This vacation home rental outside of Bossi is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library. See all vacation rentals in Bossi.
If I need to cancel my hotel reservation in Bossi, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Bossi.
Where can I learn more about changing or cancelling my trip to Bossi?
For more details about rescheduling or cancelling your trip to Bossi, go to https://www.expedia.com/service/.
What's the best pet-friendly place to stay in Bossi?
Castello di Bossi is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Bossi.
What are some hotels with pools in Bossi?
Fattoria di Vegi: Offers a rooftop terrace, an outdoor pool, and a snack bar/deli. Also, another option that features an onsite pool is Castello di Spaltenna- Small Luxury Hotels of the World. View all hotels with pools in Bossi.
What is staying in Bossi like?
Travelers to Bossi will find plenty to explore and enjoy. In Bossi, there are 20 hotels and other accommodations to choose from. Find out more about Bossi.
What are the top places to visit in Bossi?
Places to visit in the wider area include Castle of Brolio, Siena Circuit, and Cantalici Winery. You'll also find Meleto Castle and Villa a Sesta Polo Club in the area. Check out what more to see and do in Expedia's Bossi guide.
What's the weather like in Bossi?
The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Bossi is 37 inches.

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