Hotels in Bossi

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Where to stay in Bossi?

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

Castelnuovo Berardenga

$69

$168 total

includes taxes & fees

Oct 27 - Oct 28

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

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.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

2. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

$90

$108 total

includes taxes & fees

Nov 26 - Nov 27

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

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

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

A room with a view of a forest through a window, a table with a lamp, and a chair.

3. Dievole Wine Resort

Castelnuovo Berardenga

$272

$308 total

includes taxes & fees

Nov 16 - Nov 17

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

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.

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

4. Precise House Montaperti Siena

Asciano

$93

$109 total

includes taxes & fees

Nov 15 - Nov 16

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

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.

A table set for dining with a scenic view of rolling hills and distant mountains.

5. Castello di Leonina Relais

Asciano

$140

$160 total

includes taxes & fees

Nov 5 - Nov 6

A villa with a swimming pool, outdoor seating, and a tennis court.

A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

An aerial view of a property with a swimming pool, tennis court, and vineyard.

A hotel room with a bed, a nightstand, a lamp, and a view of a landscape through a window.

6. Villa Curina Resort

Castelnuovo Berardenga

$146

$165 total

includes taxes & fees

Oct 27 - Oct 28

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".

7. Hotel Executive

Scacciapensieri

$90

$103 total

includes taxes & fees

Nov 22 - Nov 23

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

A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

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.

8. Villa Montarioso

Montarioso

$76

$89 total

includes taxes & fees

Nov 15 - Nov 16

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone archway leading to a window with a view of tall trees and a distant landscape.

A stone building with a tower, surrounded by people dining at tables with candles.

9. Castello di Tornano Wine Resort

Gaiole in Chianti

$152

$176 total

includes taxes & fees

Oct 27 - Oct 28

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

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."

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

10. Four Points by Sheraton Siena

Scacciapensieri

$131

$147 total

includes taxes & fees

Nov 7 - Nov 8

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

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

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

A building with arched windows, a courtyard with a pond, and a metal fence.

11. Hotel Casafrassi

Castellina in Chianti

$57

$69 total

includes taxes & fees

Oct 29 - Oct 30

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

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

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

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

12. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

$100

$119 total

includes taxes & fees

Oct 27 - Oct 28

A courtyard with a lemon tree, potted plants, and a building with arched windows.

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

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

A large, historic building with a covered patio and a well-maintained garden.

13. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$132

$151 total

includes taxes & fees

Oct 27 - Oct 28

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

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

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.

14. Belvedere di San Leonino

Castellina in Chianti

$107

$124 total

includes taxes & fees

Oct 29 - Oct 30

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

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.

A room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

15. Sangallo Park Hotel

Vico Alto

$106

$120 total

includes taxes & fees

Nov 6 - Nov 7

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.

16. The Club House

Castelnuovo Berardenga

$357

$404 total

includes taxes & fees

Nov 1 - Nov 2

A table set for breakfast with a scenic view of hills and a cloudy sky.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

17. Palazzo di Valli

Siena

$107

$121 total

includes taxes & fees

Nov 21 - Nov 22

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

A vineyard with a sign that reads "La dolce vita" and a cart with wine bottles.

A vineyard with rows of grapevines and decorative hanging lights.

An outdoor dining area with tables and chairs, a covered walkway, and a view of a vineyard.

18. Hotel Ristorante La Dama nella Vigna

Monteriggioni

$105

$121 total

includes taxes & fees

Nov 12 - Nov 13

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

A large building with multiple rooms, surrounded by a field of lavender.

An arched brick corridor leading to a dining area with tables set for a meal.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

19. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

$364

$412 total

includes taxes & fees

Nov 4 - Nov 5

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

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

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

20. Hotel Borgo Antico

Monteroni d'Arbia

$87

$101 total

includes taxes & fees

Oct 27 - Oct 28

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Go beyond your typical stay in Bossi

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Check out reviews of Bossi hotels guests love

La Certosa di Pontignano

10/10 Excellent

"Beautiful property, staff was always helpful. Food was excellent."

Palazzo Ravizza

10/10 Excellent

"Beautiful hotel close to the historic town center and Il Campo. Nice restaurant, bar, lobby, and beautiful garden area which offers fantastic sunset views. Room was very nice as well. A lovely place to stay in Siena."

Fattoria di Vegi

10/10 Excellent

"Phenomenal. We stayed 4 nights of our honeymoon at the Fattoria de Vegi and can't wait to return in the future. The staff were all so friendly and helpful, the property is set in the most beautiful quiet location with many places to lounge and explore. Everything we ate both for breakfast and from the restaurant for dinner was excellent. It was our favourite stay of the 4 locations we visited on our trip in Italy! Would recommend a cooking class also, it was a lovely addition to our stay. You can tell the attention to detail taken throughout the renovations to turn this property into an absolute class destination."

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

Hotel Athena

10/10 Excellent

"Over all a good hotel in a good location, a little dated but clean and breakfast good"

Hotel Chiusarelli

10/10 Excellent

"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"

NH Siena

10/10 Excellent

"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Excellent location. Very nice service."

Hotel Minerva

10/10 Excellent

"The check-in staff were very friendly, helpful, and spoke English. The €20 parking in their garage was very nice and convenient, especially when it rained. Nice view from the room."

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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