Hotels in Bossi

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Where to stay in Bossi?

A courtyard with stone walls, arched windows, and potted plants.

A swimming pool with a clear view of the surrounding landscape, including trees and distant hills.

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.

1. Castello di Bossi

Castelnuovo Berardenga

$72

$172 total

includes taxes & fees

Nov 3 - Nov 4

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 interior corridor with arches, columns, and a brick wall.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

2. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

$84

$102 total

includes taxes & fees

Nov 2 - Nov 3

A terrace with multiple sun loungers and a scenic view of green fields and hills.

An indoor swimming pool with lounge chairs and a view of the countryside.

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.

A spa room with a reception desk, a massage chair, and a window with blinds.

3. Precise House Montaperti Siena

Asciano

$95

$111 total

includes taxes & fees

Nov 9 - Nov 10

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.

4. Castello di Tornano Wine Resort

Gaiole in Chianti

$152

$176 total

includes taxes & fees

Oct 25 - Oct 26

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.

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

A courtyard with brick buildings, a column, and potted plants.

5. Castello di Leonina Relais

Asciano

$147

$168 total

includes taxes & fees

Oct 31 - Nov 1

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 cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

6. Dievole Wine Resort

Castelnuovo Berardenga

$272

$308 total

includes taxes & fees

Nov 9 - Nov 10

A modern building with a sign reading "Palace Hotel."

A red building with a reception sign, a bicycle, potted plants, and luggage.

A modern building entrance with a glass door reflecting a parking lot and trees.

7. Palace Hotel Due Ponti

Due Ponti

$81

$93 total

includes taxes & fees

Nov 1 - Nov 2

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.

An outdoor dining area with tables and chairs, covered by a canopy, and surrounded by greenery.

A hotel entrance with a sign reading "HOTEL EXPO".

8. Hotel Executive

Scacciapensieri

$90

$103 total

includes taxes & fees

Nov 1 - Nov 2

A pathway lined with trees and a large pot in the center.

A breakfast buffet with pastries and a coffee machine.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

9. Villa Montarioso

Montarioso

$76

$89 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

A bathroom with a sink, mirror, and shower.

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.

10. Sangallo Park Hotel

Vico Alto

$95

$108 total

includes taxes & fees

Nov 15 - Nov 16

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

11. Hotel Casafrassi

Castellina in Chianti

$60

$73 total

includes taxes & fees

Oct 16 - Oct 17

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

12. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

$91

$109 total

includes taxes & fees

Oct 21 - Oct 22

A building with a sign reading 'HOTEL SAN CARLO.' It features a flat roof, a large entrance with glass doors, and a paved courtyard.

A buffet counter with various food items including pastries, a pie, and a bowl of eggs.

A hotel lobby with a row of sofas and armchairs, a central coffee table, and a television mounted on the wall.

A modern waiting area with white chairs, glass tables, and a reception desk.

13. Best Western Hotel San Marco

Siena

$85

$99 total

includes taxes & fees

Oct 18 - Oct 19

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

14. Four Points by Sheraton Siena

Scacciapensieri

$134

$151 total

includes taxes & fees

Nov 15 - Nov 16

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

15. The Club House

Castelnuovo Berardenga

$356

$403 total

includes taxes & fees

Nov 15 - Nov 16

A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.

A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

A restaurant with a high ceiling, brick walls, and a bar area with a variety of bottles. There are tables and chairs for dining, and a television is visible on the right side.

A bedroom with a bed, a sofa, a desk, and a TV. There are windows with curtains and a view of greenery outside.

16. Hotel Borgo Antico

Monteroni d'Arbia

$107

$123 total

includes taxes & fees

Oct 30 - Oct 31

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 room with a large window offering a view of a landscaped garden with trees and a pathway.

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

17. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$189

$214 total

includes taxes & fees

Oct 28 - Oct 29

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 restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

18. Hotel Le Fontanelle

Castelnuovo Berardenga

$547

$613 total

includes taxes & fees

Oct 28 - Oct 29

A historic stone building with multiple windows and a courtyard.

A stone building with outdoor seating and a garden with roses.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

19. Borgo San Felice Resort

Castelnuovo Berardenga

$769

$857 total

includes taxes & fees

Oct 25 - Oct 26

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A person relaxing in a hot tub with a view of a building and trees in the background.

A poolside area with lounge chairs and a view of the night sky.

A rustic stone building with a garden in front.

20. Belvedere di San Leonino

Castellina in Chianti

$107

$124 total

includes taxes & fees

Oct 27 - Oct 28

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Go beyond your typical stay in Bossi

Pet friendly

Apartment

Apart hotel

Spa

Pool

Hot tub

Family friendly

Farm

Check out reviews of Bossi hotels guests love

Palazzo Ravizza

10/10 Excellent

"Lovely hotel inside the city walls, if you are driving there and want to take advantage of the hotel car park (availability not guaranteed) you have to follow quite specific instructions to get there so as not to get a fine, they are quite easy to follow though. Dogs accepted and they provided dog beds and water for the dogs which was nice, the dogs are also allowed throughout the hotel. The views from the bedroom were amazing, as is the same from the lovely garden & terrace. Breakfast was great, lovely bread and the best marmalade ever, as well as cake, eggs, etc. bar is just open from 5pm but you can get a drink earlier if it takes your fancy"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Gorgeous hotel in the heart of historic Siena."

Hotel Italia

10/10 Excellent

"Staff and hotel was great."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Il Chiostro del Carmine

10/10 Excellent

"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."

Fattoria di Vegi

10/10 Excellent

"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"Beautiful Borgo with views over Sienna and wonderful Tuscan countryside. In peak summer there is a family pool and adults only pool. The family pool was quiet and nice area to relax. About 20-30 mins to Siena we explored lots of lovely hill top places for dinner each night. Pool side dining was ok, club sandwiches that type of thing not extensive choice but adequate. Stunning views, good location to explore surrounding area. Would definitely recommend. I stayed with my family two boys age 9 and 13 and they loved it. Accommodation was very comfortable and spacious."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Frequently asked questions

What hotels do travelers like in Bossi?

Guests like Hotel Athena, La Certosa di Pontignano and Grand Hotel Continental Siena – Starhotels Collezione.

Can I book a refundable hotel in Bossi?

If you need the flexibility to change your travel plans to Bossi, most accommodations offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Bossi if I want a vacation home instead of a hotel?

You'll find 5 vacation homes on our site.

What will the weather in Bossi be like during my vacation?

The warmest months in Bossi are usually August and July with an average temp of 72°F. January and February are the chilliest months when the average temp is 44°F. The rainiest months are November and October.

Why should I book my Bossi accommodation with Hotels.com?

There are plenty of reasons to book your Bossi travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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