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Oct 26 - Oct 27
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Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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Our top choices for San Chimento hotels

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 dining area with wooden tables and chairs, large windows offering a view of a forested landscape.
A breakfast buffet with various pastries, fruits, and beverages.

1. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
Canada
Patricia
$80 nightly
$93 total
Nov 13 - Nov 14
Total with taxes and fees
Villa Sabolini
A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.
An outdoor patio with stone flooring, a table with chairs, and potted plants.
Breakfast meal

2. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
United States
JOHN
$111 nightly
$130 total
Nov 8 - Nov 9
Total with taxes and fees
Hotel Borgo San Luigi
A courtyard with a statue, stone walls, and a reception sign.
A narrow cobblestone street flanked by stone buildings with arched windows and a central potted plant.
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.

3. Relais Della Rovere

Relais Della Rovere
Colle di Val d'Elsa
United States
Megan
$129 nightly
$146 total
Oct 30 - Oct 31
Total with taxes and fees
Relais Della Rovere
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A spacious dining area with multiple round tables, white tablecloths, and blue chair covers.
A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.
A neatly made breakfast tray on a bed with a tray of bread, fruit, juice, and tea, in a room with a bed, curtains, and a painting on the wall.

4. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
Canada
Frank
$111 nightly
$130 total
Nov 4 - Nov 5
Total with taxes and fees
Hotel Il Piccolo Castello
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 modern bedroom with a large bed, a built-in wardrobe, a seating area, and a view of the outdoors.
A vineyard with rows of grapevines and decorative hanging lights.

5. Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
United States
Amanda
$98 nightly
$113 total
Nov 12 - Nov 13
Total with taxes and fees
Hotel Ristorante La Dama nella Vigna
A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.
A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.
A wooden gazebo with a thatched roof overlooking a landscaped garden with trees and a view of hills.
A courtyard with stone buildings, a thatched-roof structure, and potted plants.

6. Relais Castel Bigozzi

Relais Castel Bigozzi
Monteriggioni
United States
Nissan
$89 nightly
$106 total
Nov 26 - Nov 27
Total with taxes and fees
Relais Castel Bigozzi
A swimming pool, steps, and a grassy area with umbrellas.
A tiled shower area with a square light fixture above the showerhead.
A spa area with wooden benches and a glass partition, a modern bathroom with a large sink, and a corridor leading to another room.
A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

7. Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
Colle di Val d'Elsa
Canada
Maria
$109 nightly
$124 total
Nov 26 - Nov 27
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 hotel room with a bed, a desk, a chair, and a window with curtains.
A spacious living area with a sofa, a coffee table, and a view of buildings through large windows.
A spacious lobby with a reception desk, a staircase with a glass railing, and a wooden floor.

8. Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
Colle di Val d'Elsa
Canada
Sheila
$79 nightly
$90 total
Nov 26 - Nov 27
Total with taxes and fees
Hotel La Vecchia Cartiera
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.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
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
Rodolfo
$90 nightly
$108 total
Nov 26 - Nov 27
Total with taxes and fees
La Certosa di Pontignano - Place of Charme
A yellow building with stone pillars, multiple windows, and a statue in the garden.
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.
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

10. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United Kingdom
James
$104 nightly
$121 total
Oct 28 - Oct 29
Total with taxes and fees
Villa San Lucchese
A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.
A modern living room with a glass coffee table, white sofas, and decorative plants.
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.

11. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Andras
$65 nightly
$75 total
Nov 22 - Nov 23
Total with taxes and fees
Hotel Executive
A stone building with a swimming pool, surrounded by trees and a view of the landscape.
A stone building with a paved entrance and a well-maintained garden with potted plants.
A stone-walled terrace with a table set for two, a bottle, and candles.
A stone wall with a rustic stone building partially visible behind it.

12. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
Canada
Doug
$165 nightly
$187 total
Oct 27 - Oct 28
Total with taxes and fees
Relais la Costa - Dimora Storica
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 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.

13. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
United Kingdom
Stuart
$57 nightly
$69 total
Oct 29 - Oct 30
Total with taxes and fees
Hotel Casafrassi
A pathway lined with trees and a large pot in the center.
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.
A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

14. Villa Montarioso

Villa Montarioso
Montarioso
Canada
Michael
$76 nightly
$89 total
Nov 15 - Nov 16
Total with taxes and fees
Villa Montarioso
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.

15. Hotel Villa San Giorgio

Hotel Villa San Giorgio
Poggibonsi
United States
Arik
$60 nightly
$66 total
Nov 15 - Nov 16
Total with taxes and fees
Hotel Villa San Giorgio
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
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 rustic stone building with a garden in front.

16. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
Canada
Kevork
$107 nightly
$124 total
Oct 29 - Oct 30
Total with taxes and fees
Belvedere di San Leonino
A table set for breakfast with a scenic view of hills and a cloudy sky.
A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.
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.

17. Palazzo di Valli

Palazzo di Valli
Siena
United States
Luanne
$107 nightly
$121 total
Nov 21 - Nov 22
Total with taxes and fees
Palazzo di Valli
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 room with a wooden desk, a laptop, a television displaying a news channel, and a window with curtains.

18. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Marcio Tadeu
$88 nightly
$101 total
Nov 6 - Nov 7
Total with taxes and fees
Sangallo Park Hotel
A courtyard with a lemon tree, potted plants, and a building with arched windows.
A large, historic building with a covered patio and a well-maintained garden.
A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.
A swimming pool surrounded by lush greenery and a stone pathway.

19. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Canada
Anita
$119 nightly
$136 total
Oct 28 - Oct 29
Total with taxes and fees
Villa Scacciapensieri Boutique Hotel
A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.
A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.
A swimming pool with lounge chairs and umbrellas, stone buildings, and a clear sky.
A stone building with a balcony, surrounded by lush greenery and a view of distant hills.

20. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
Sovicille
United States
Rene
$147 nightly
$167 total
Nov 1 - Nov 2
Total with taxes and fees
Relais Le Macine di Stigliano
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Top San Chimento Hotel Reviews

Fattoria di Vegi

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."
Niklas 4-night trip
Posted 12 hours ago
Fattoria di Vegi
Hotel Borgo San Luigi

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."
John 2-night trip
Posted 20 hours ago
Hotel Borgo San Luigi
Hotel Athena

Hotel Athena

10/10 Excellent
"Over all a good hotel in a good location, a little dated but clean and breakfast good"
Suzanne 2-night trip
Posted 1 day ago
Hotel Athena
Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"
William 2-night trip
Posted 2 days ago
Hotel Chiusarelli
NH Siena

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"
Rakhshan 1-night trip
Posted 3 days ago
NH Siena
Poderi Arcangelo

Poderi Arcangelo

10/10 Excellent
"Fantastic experience all around from the the food, the wine, THE VIEWS, and the late October weather gifted us an afternoon poolside. Our room was wonderful and passed every expectation. Five stars!"
Christine 2-night trip
Posted 3 days ago
Poderi Arcangelo
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good
"Excellent location. Very nice service."
mauricio 1-night trip
Posted 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Absolutely lovely hotel. Best one we stayed at in Italy - in retrospect, we wish we booked to stay here a second night. The location is quiet and isolated so stars are visible at night, plenty of parking, and breakfast is worth the 20 EURS, best breakfast options we had during our stay. Highly recommend, 10/10."
Maya 1-night trip
Posted 4 days ago
Hotel Casolare Le Terre Rosse
Hotel Minerva

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."
Greg 1-night trip
Posted 4 days ago
Hotel Minerva

More cheap stays in San Chimento

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
$51 nightly
$59 total
Nov 25 - Nov 26
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
$69 nightly
$79 total
Nov 25 - Nov 26
Total with taxes and fees
7.8/10 Good! (453 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
$78 nightly
$90 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (114 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
$88 nightly
$100 total
Nov 4 - Nov 5
Total with taxes and fees
10/10 Exceptional! (52 reviews)
Torre del Fuggisole
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence
Borgo Tignano

Borgo Tignano

Località Tignano Volterra PI
Get ratesBorgo Tignano

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 $59 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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