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Oct 18 - Oct 19
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Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

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Our top choices for San Chimento hotels

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
Pool
An outdoor patio with stone flooring, a table with chairs, and potted plants.
A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

1. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
United States
yekta
$102 nightly
$120 total
Nov 9 - Nov 10
Total with taxes and fees
Hotel Borgo San Luigi
A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.
A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.
A breakfast buffet with various pastries, fruits, and beverages.
A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.

2. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
Canada
Patricia
$80 nightly
$93 total
Nov 3 - Nov 4
Total with taxes and fees
Villa Sabolini
A person sitting in a corner of a room with tiled walls and a bench.
A fountain in a park with tall trees and a clear sky.
A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.
A poolside area with lounge chairs, umbrellas, and a swimming pool.

3. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
Canada
Frank
$104 nightly
$123 total
Nov 13 - Nov 14
Total with taxes and fees
Hotel Il Piccolo Castello
A courtyard with a statue, stone walls, and a reception sign.
An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.
A spacious room with a high ceiling, wooden beams, and a chandelier. There are tables and chairs arranged for dining, and a wine rack filled with bottles.
A wooden pathway leading to a pool area with a gazebo and potted plants.

4. Relais Della Rovere

Relais Della Rovere
Colle di Val d'Elsa
United States
Megan
$129 nightly
$147 total
Oct 30 - Oct 31
Total with taxes and fees
Relais Della Rovere
A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.
A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.
A courtyard with stone buildings, a thatched-roof structure, and potted plants.
A wooden gazebo with a thatched roof overlooking a landscaped garden with trees and a view of hills.

5. Relais Castel Bigozzi

Relais Castel Bigozzi
Monteriggioni
United States
Nissan
$93 nightly
$111 total
Nov 17 - Nov 18
Total with taxes and fees
Relais Castel Bigozzi
A person sitting in a hot tub with a waterfall feature in the background.
A tiled shower area with a square light fixture above the showerhead.
A hotel room with a large bed, a desk, and a chair, a view of a city through the window, and a ceiling light.
A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

6. Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
Colle di Val d'Elsa
Canada
Maria
$111 nightly
$127 total
Nov 17 - Nov 18
Total with taxes and fees
Hotel Palazzo San Lorenzo & SPA
A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.
A spacious lobby with a reception desk, a staircase with a glass railing, and a wooden floor.
A spacious living area with a sofa, a coffee table, and a view of buildings through large windows.
A bar area with wooden bar stools, a counter with bottles, and a tiled floor.

7. Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
Colle di Val d'Elsa
Canada
Sheila
$79 nightly
$91 total
Nov 17 - Nov 18
Total with taxes and fees
Hotel La Vecchia Cartiera
A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery.
An outdoor patio area with tables and chairs, a reception desk, and potted plants.
A stone building with a rustic exterior, surrounded by lush greenery and outdoor seating areas.

8. Hotel Villa San Giorgio

Hotel Villa San Giorgio
Poggibonsi
United States
Arik
$60 nightly
$66 total
Nov 8 - Nov 9
Total with taxes and fees
Hotel Villa San Giorgio
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.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
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.

9. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
United States
Leslie
$82 nightly
$99 total
Nov 18 - Nov 19
Total with taxes and fees
La Certosa di Pontignano - Place of Charme
A stone building with a swimming pool, surrounded by trees and a view of the landscape.
A stone wall with a rustic stone building partially visible behind it.
A stone-walled terrace with a table set for two, a bottle, and candles.
A stone building with a paved entrance and a well-maintained garden with potted plants.

10. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
Canada
Doug
$152 nightly
$172 total
Oct 21 - Oct 22
Total with taxes and fees
Relais la Costa - Dimora Storica
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.
A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.
A room with a sofa, a desk, a bunk bed, and a patterned floor.
A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

11. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United Kingdom
James
$111 nightly
$122 total
Nov 17 - Nov 18
Total with taxes and fees
Villa San Lucchese
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A building with arched windows, a courtyard with a pond, and a metal fence.
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.

12. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
United Kingdom
Stuart
$56 nightly
$68 total
Oct 26 - Oct 27
Total with taxes and fees
Hotel Casafrassi
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.
A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.
An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

13. Palazzo di Valli

Palazzo di Valli
Siena
United States
Luanne
$102 nightly
$116 total
Nov 18 - Nov 19
Total with taxes and fees
Palazzo di Valli
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 room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.
A bathroom with a sink, mirror, and shower.

14. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Marcio Tadeu
$91 nightly
$103 total
Nov 6 - Nov 7
Total with taxes and fees
Sangallo Park Hotel
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".
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.

15. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Andras
$67 nightly
$77 total
Nov 1 - Nov 2
Total with taxes and fees
Hotel Executive
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 rustic stone building with a garden in front.
A person relaxing in a hot tub with a view of a building and trees in the background.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

16. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
Canada
Kevork
$107 nightly
$125 total
Oct 27 - Oct 28
Total with taxes and fees
Belvedere di San Leonino
A stone building with a courtyard, surrounded by lush greenery and a hillside.
A stone building with a balcony, surrounded by lush greenery and a view of distant hills.
A window with white curtains, a view of buildings, and greenery.
A swimming pool with lounge chairs and umbrellas, stone buildings, and a clear sky.

17. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
Sovicille
United States
Rene
$147 nightly
$168 total
Nov 12 - Nov 13
Total with taxes and fees
Relais Le Macine di Stigliano
A buffet counter with various food items including pastries, a pie, and a bowl of eggs.
A hotel entrance with a glass door, a metal frame, and a light fixture above.
A conference room with rows of chairs, a projector, a whiteboard, and a podium.
A hotel room with a bed, bedside tables, a desk with a chair, a television, and a window with curtains.

18. Best Western Hotel San Marco

Best Western Hotel San Marco
Siena
United Kingdom
C.K.
$92 nightly
$105 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Hotel San Marco
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.
A lobby with a reception desk, a staircase, and seating areas.
A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.
A historic square with stone buildings, a central fountain, and a tower.

19. La Cisterna

La Cisterna
San Gimignano City Centre
United States
Kathy Ann
$89 nightly
$105 total
Nov 5 - Nov 6
Total with taxes and fees
La Cisterna
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.
A clear blue pool with lounge chairs and a stone building in the background.
A stone building with a wooden bench outside.

20. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
United States
Monica
$112 nightly
$126 total
Oct 21 - Oct 22
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
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Top San Chimento Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."
Victor 4-night trip
Posted 3 days ago
Hotel Chiusarelli
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Absolutely amazing stay! The room was clean, large with a great view. The staff was always willing to help. Could not have asked for more. Highly recommend!"
Virginia 2-night trip
Posted 3 days ago
La Certosa di Pontignano
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."
jacquelyn 5-night trip
Posted 5 days ago
Hotel Casolare Le Terre Rosse
Hotel Italia

Hotel Italia

10/10 Excellent
"Staff and hotel was great."
Suzanne 1-night trip
Posted 6 days ago
Hotel Italia
Castello di Spaltenna- Small Luxury Hotels of the World

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."
Michelle 3-night trip
Posted 7 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Il Chiostro del Carmine

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."
Katharine 3-night trip
Posted 8 days ago
Il Chiostro del Carmine
Fattoria di Vegi

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!"
Lauren 1-night trip
Posted 11 days ago
Fattoria di Vegi
Four Points by Sheraton Siena

Four Points by Sheraton Siena

8/10 Good
"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."
Rajendra 3-night trip
Posted 13 days ago
Four Points by Sheraton Siena

More cheap stays in San Chimento

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
$53 nightly
$61 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (259 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
$68 nightly
$78 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (453 reviews)
Piccolo Hotel Etruria
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
$77 nightly
$89 total
Nov 4 - Nov 5
Total with taxes and fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
$88 nightly
$100 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (113 reviews)
Albergo Centrale
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
$152 nightly
$173 total
Nov 3 - Nov 4
Total with taxes and fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

Frequently asked questions

What is the best area to stay in San Chimento?
The best area to stay in San Chimento is within the historic walled city center itself, offering an authentic Tuscan experience.This area is characterized by its narrow, cobblestone streets, medieval architecture, and historic landmarks like the Duomo di San Chimento and the Palazzo Pretorio. It's a pedestrian-friendly zone with many local shops, trattorias, and cafes tucked away in its winding alleys and small piazzas. Couples will find this area particularly appealing for its romantic setting and the ease of exploring on foot.For families, staying just outside the city walls, particularly along the Viale delle Mura, provides a good balance. Here, you'll find accommodations that often include more space, gardens, or pools, offering a quieter retreat after a day of sightseeing.
When is the best time to go to San Chimento?
The best time to go to San Chimento, Tuscany, Italy is during the spring (April to early June) or autumn (September to October) for pleasant weather and fewer crowds.During these shoulder seasons, the weather is mild and comfortable, ideal for exploring the rolling hills, vineyards, and historic towns that define the Tuscan landscape. Spring brings blooming wildflowers and lush green scenery, while autumn offers vibrant fall foliage and harvest festivals. You'll find it easier to book accommodations and dinner reservations without the peak summer rush.Couples looking for a romantic escape will appreciate the tranquil beauty of San Chimento during these times. You can enjoy wine tastings at local vineyards, leisurely walks through olive groves, and intimate dinners at trattorias without the bustling crowds of mid-summer. The cooler temperatures are also great for cycling tours through the countryside.Families traveling with children will also find these times advantageous. The milder weather makes outdoor activities more enjoyable for all ages, from exploring medieval castles to picnicking in scenic spots.
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 San Chimento.
How much is the nightly rate at a San Chimento hotel?
Prices for hotels in San Chimento often vary, but you can find a great deal from $53 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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