Bossi Holiday Rentals, Castelnuovo Berardenga: Private House Rentals

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Our top choices for Bossi hotels

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

A rustic interior with a stone wall, a wooden staircase, and a view of the outdoors.

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

A covered outdoor area with brick arches, potted plants, and a door leading to a building.

1. Castello di Bossi

Castelnuovo Berardenga

CESAR JAVIER

฿2,320

฿5,694 total

includes taxes & fees

25 Oct - 26 Oct

A kitchen with a wooden cabinet, a window, and a staircase.

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 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

Rodolfo

฿3,203

฿3,826 total

includes taxes & fees

16 Nov - 17 Nov

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 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.

3. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Anita

฿4,456

฿5,091 total

includes taxes & fees

26 Oct - 27 Oct

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

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

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

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

4. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

฿9,191

฿10,412 total

includes taxes & fees

16 Nov - 17 Nov

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

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

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

A modern living room with a glass coffee table, white sofas, and decorative plants.

5. Hotel Executive

Scacciapensieri

Andras

฿3,053

฿3,472 total

includes taxes & fees

22 Nov - 23 Nov

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 table set for breakfast with various dishes, drinks, and a newspaper.

6. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

฿20,382

฿22,799 total

includes taxes & fees

31 Oct - 1 Nov

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

A spacious living area with a wooden coffee table, a large potted plant, and a sofa.

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

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

7. Precise House Montaperti Siena

Asciano

Dieter

฿3,147

฿3,689 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A sunlit patio with a glass roof, stone walls, and outdoor seating.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

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

Gaiole in Chianti

Michelle

฿11,140

฿12,632 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

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

9. Four Points by Sheraton Siena

Scacciapensieri

Ralph

฿4,413

฿4,968 total

includes taxes & fees

7 Nov - 8 Nov

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

A bathroom with a sink, mirror, and shower.

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

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

10. Sangallo Park Hotel

Vico Alto

Marcio Tadeu

฿3,593

฿4,066 total

includes taxes & fees

13 Nov - 14 Nov

A historic stone building with multiple windows and a courtyard.

A pool area with lounge chairs and a service person attending to a guest.

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.

11. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

฿25,986

฿28,963 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

12. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

฿12,397

฿14,015 total

includes taxes & fees

3 Nov - 4 Nov

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

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

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

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

13. Castello di Tornano Wine Resort

Gaiole in Chianti

Karina

฿5,133

฿5,949 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

14. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

฿3,706

฿4,379 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

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

15. The Club House

Castelnuovo Berardenga

Natalyn

฿12,056

฿13,640 total

includes taxes & fees

2 Nov - 3 Nov

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.

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.

16. Castello di Leonina Relais

Asciano

Brooke

฿4,714

฿5,412 total

includes taxes & fees

5 Nov - 6 Nov

A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.

An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.

A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.

17. Il Verreno

Ambra

Minna

฿6,742

฿7,567 total

includes taxes & fees

31 Oct - 1 Nov

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A modern living room with a white sofa, armchairs, and a coffee table.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

18. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

฿9,077

฿10,212 total

includes taxes & fees

5 Nov - 6 Nov

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

19. Belvedere di San Leonino

Castellina in Chianti

Kevork

฿3,627

฿4,217 total

includes taxes & fees

27 Oct - 28 Oct

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 breakfast buffet with pastries and a coffee machine.

20. Villa Montarioso

Montarioso

Michael

฿2,757

฿3,222 total

includes taxes & fees

3 Nov - 4 Nov

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Top Bossi Hotel Reviews

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."

Il Chiostro del Carmine

8/10 Good

"Breakfast"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

La Certosa di Pontignano

10/10 Excellent

"Great location amazing place"

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."

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."

More cheap stays in Bossi

Cannon d'Oro

Via Montanini 28 Siena SI

฿1,805

฿2,099 total

21 Nov - 22 Nov

includes taxes & fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿2,562

฿2,932 total

12 Nov - 13 Nov

includes taxes & fees

7.8/10 Good! (453 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

฿2,646

฿3,024 total

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (114 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿2,969

฿3,379 total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (52 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Get rates

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 traveller data. Other good choices for your stay in 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 holiday rentals that Bossi has to offer?

Borgo Argiano: This holiday home rental outside of Bossi 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 kitchenware. You can relax into your holiday 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! Most hotel room reservations are refundable if 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, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Bossi.

What's the best dog-friendly accommodation option in Bossi?

Castello di Bossi is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Bossi.

What are some accommodation options with pools in Bossi?

Fattoria di Vegi: Offers a rooftop terrace, an outdoor pool and a snack bar/deli. Another choice that features an on-site pool is Castello di Spaltenna- Small Luxury Hotels of the World. View all hotels with pools in Bossi.

What is staying in Bossi like?

Travellers to Bossi will find plenty to explore and enjoy. In Bossi, there are 20 hotels and other accommodation options 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. Take a look at what more there is to see and do in Expedia's Bossi guide.

What's the seasonal weather like in Bossi?

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 Bossi is 946 mm.

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Book Hotels in Bossi on Expedia.it

Find hotels in Bossi from ฿2,099

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Bossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Bossi hotels

1. Castello di Bossi

2. La Certosa di Pontignano - Place of Charme

3. Villa Scacciapensieri Boutique Hotel

4. Dievole Wine Resort

5. Hotel Executive

6. Hotel Le Fontanelle

7. Precise House Montaperti Siena

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

9. Four Points by Sheraton Siena

10. Sangallo Park Hotel

11. Borgo San Felice Resort

12. Borgo Scopeto Wine & Country Relais

13. Castello di Tornano Wine Resort

14. Ultimo Mulino Wellness Country Hotel

15. The Club House

16. Castello di Leonina Relais

17. Il Verreno

18. Chapter Chianti, a Member of Design Hotels

19. Belvedere di San Leonino

20. Villa Montarioso

Top Bossi Hotel Reviews

NH Siena

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Minerva

Il Chiostro del Carmine

Hotel Italia

La Certosa di Pontignano

Castello di Spaltenna- Small Luxury Hotels of the World

Four Points by Sheraton Siena

Borgo Vescine

More cheap stays in Bossi

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Villa Norcenni Aparthotel

Frequently asked questions

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