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Oct 6 - Oct 7
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Oct 7 - Oct 8
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Oct 9 - Oct 11
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Our top choices for Pentolina hotels

A stone building with a courtyard, surrounded by lush greenery and a hillside.
A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.
A stone building with a balcony, surrounded by lush greenery and a view of distant hills.
A swimming pool with lounge chairs and umbrellas, stone buildings, and a clear sky.

1. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
Sovicille
United States
kevin
$150 nightly
$171 total
Nov 2 - Nov 3
Total with taxes and fees
Relais Le Macine di Stigliano
A pool with a modern water feature and a stone structure.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
A buffet table with various desserts and a long dining area with tables and chairs.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

2. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
$84 nightly
$93 total
Oct 13 - Oct 14
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.
A brick wall with a number plate and a metal gate.
A bedroom with a bed, two bedside tables with lamps, a window with curtains, and a painting on the wall.
A staircase with a metal railing leading to a landing.

3. L'Aia di Argia

L'Aia di Argia
Monteroni d'Arbia
United States
mario
$67 nightly
$78 total
Nov 6 - Nov 7
Total with taxes and fees
L'Aia di Argia
A modern building with a sign reading "Palace Hotel."
A modern building entrance with a glass door reflecting a parking lot and trees.
A red building with a reception sign, a bicycle, potted plants, and luggage.
A buffet setup with various food items including yogurt cups, fruits, and a bowl of grapes.

4. Palace Hotel Due Ponti

Palace Hotel Due Ponti
Due Ponti
United States
Adam
$72 nightly
$83 total
Nov 1 - Nov 2
Total with taxes and fees
Palace Hotel Due Ponti
Interior
A conference room with a long table, blue chairs, a whiteboard, and a projector screen.
A hotel room with a bed, bedside tables, a desk, and a chair.
A bakery display with various pastries and bread, including croissants and cakes, with labels indicating the type of pastry.

5. Best Western Hotel San Marco

Best Western Hotel San Marco
Siena
United Kingdom
C.K.
$92 nightly
$107 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Hotel San Marco
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 arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.
A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

6. Palazzo di Valli

Palazzo di Valli
Siena
United States
Payton
$119 nightly
$135 total
Nov 3 - Nov 4
Total with taxes and fees
Palazzo di Valli
A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.
A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.
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.

7. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
Australia
Andrew
$80 nightly
$93 total
Nov 3 - Nov 4
Total with taxes and fees
Villa Sabolini
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.

8. Hotel Borgo Antico

Hotel Borgo Antico
Monteroni d'Arbia
United Kingdom
Charles
$94 nightly
$109 total
Oct 31 - Nov 1
Total with taxes and fees
Hotel Borgo Antico
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 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.

9. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Leslie
$89 nightly
$107 total
Oct 21 - Oct 22
Total with taxes and fees
La Certosa di Pontignano
A modern lobby with white leather sofas, a glass coffee table, and potted plants.
A hotel room with a bed, bedside table, and a mirror. There is a small desk with a chair and a vase of flowers. The room has a modern design with a neutral color palette.
A spacious lobby with white furniture, a coffee station, and a view of the outdoors.
A modern kitchen with dark wooden cabinets, a dining table set with plates, glasses, and cutlery, and a vase of flowers on the right.

10. ApartHotel Anghel

ApartHotel Anghel
Siena
Netherlands
Lauro
$66 nightly
$78 total
Nov 5 - Nov 6
Total with taxes and fees
ApartHotel Anghel
A pathway lined with trees and a large pot in the center.
A breakfast buffet with pastries and a coffee machine.
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.

11. Villa Montarioso

Villa Montarioso
Montarioso
Canada
Michael
$79 nightly
$93 total
Oct 15 - Oct 16
Total with taxes and fees
Villa Montarioso
A hotel entrance with a reception area, glass doors, and a sign above reading "Hotel i Platani".
A garden area with potted plants and a fence.
A hotel room with a bed, a bedside table with a cup and a small plate, a wall-mounted heater, and a window with yellow curtains.
A hotel reception area with a wooden reception desk, a clock, a fire alarm, and a cityscape painting on the wall.

12. Hotel I Platani

Hotel I Platani
Monteriggioni
United States
Jorge
$68 nightly
$80 total
Nov 2 - Nov 3
Total with taxes and fees
Hotel I Platani
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A rustic dining area with brick walls, hanging plants, and candle-lit tables.
A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.
A bathroom with a bathtub, a chandelier, and a view of the outdoors.

13. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
United States
Rachel
$1,122 nightly
$1,246 total
Oct 31 - Nov 1
Total with taxes and fees
Borgo Santo Pietro
A wooden lattice structure with a wall-mounted sun relief, a table with breakfast items, and a red cushioned chair.
A reception desk with a framed painting above it, a small table with a cup and a book, and a door in the background.
An outdoor patio with a table set for two, surrounded by lush greenery and a tiled floor.
A two-story house with a garden pathway leading to the entrance.

14. Hotel Ristorante Piccolo Chianti

Hotel Ristorante Piccolo Chianti
Acquacalda
United States
Michael
$77 nightly
$88 total
Nov 6 - Nov 7
Total with taxes and fees
Hotel Ristorante Piccolo Chianti
A stone building with a swimming pool, surrounded by trees and a view of the landscape.
A spacious living room with a wooden staircase, a sofa, a dining table, and a radiator.
A stone wall with a rustic stone building partially visible behind it.
A stone building with a paved entrance and a well-maintained garden with potted plants.

15. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
Canada
Doug
$153 nightly
$173 total
Oct 13 - Oct 14
Total with taxes and fees
Relais la Costa - Dimora Storica
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.

16. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Andras
$66 nightly
$76 total
Nov 1 - Nov 2
Total with taxes and fees
Hotel Executive
A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
An outdoor patio with stone flooring, a table with chairs, and potted plants.
Pool
A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

17. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
Canada
Raman
$108 nightly
$126 total
Nov 4 - Nov 5
Total with taxes and fees
Hotel Borgo San Luigi
A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.
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.
A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.

18. Relais Castel Bigozzi

Relais Castel Bigozzi
Monteriggioni
United States
Paul
$99 nightly
$117 total
Nov 3 - Nov 4
Total with taxes and fees
Relais Castel Bigozzi
A stone staircase leading to a gated entrance, surrounded by lush greenery and a well-maintained lawn.
A swimming pool at night with a stone building in the background.
A buffet table with various food items and glass containers, set in an outdoor area with a wooden ceiling and a view of trees.
A rustic stone building with a small patio area featuring a terracotta pot with flowers, a metal chair, and a small table.

19. Tenuta Decimo

Tenuta Decimo
San Gimignano
United States
FLOR
$47 nightly
$57 total
Oct 26 - Oct 27
Total with taxes and fees
Tenuta Decimo
A hotel entrance with a double door, two wall-mounted light fixtures, and a sign indicating a no-smoking policy.
A buffet table with various breakfast items including pastries, fruits, and beverages.
A row of sun loungers with umbrellas, a stone wall, and a view of a hillside with trees.
A poolside area with lounge chairs, a lifebuoy, and a stone wall.

20. Hotel La Colonna

Hotel La Colonna
Siena
United Kingdom
Terese
$46 nightly
$54 total
Nov 3 - Nov 4
Total with taxes and fees
Hotel La Colonna
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Top Pentolina Hotel Reviews

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

8/10 Good
"Concierge desk - Francesca - was off the charts! Was hoping for more modernized room with better views"
Christopher 4-night trip
Posted 15 hours ago
Borgo Scopeto Wine & Country Relais
Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"We spent four nights in Siena as a base for other tuscan adventures. Loved the authenticity of the piazza. The staff are exceptional and very attentive. The contential breakfast is well appointed and available coffee choices excellent. Don't miss sunset in the back garden bellicimo."
Kevin 4-night trip
Posted 16 hours ago
Palazzo Ravizza
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 1 day ago
Castiglion del Bosco, A Rosewood Hotel
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 1 day ago
Four Points by Sheraton Siena
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"The entire estate was perfectly curated, every aspect was completely flawless. Food and wine…. 10/10. Best place we’ve ever stayed."
Timothy 4-night trip
Posted 2 days ago
Fattoria di Vegi
Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"Room clean large spacious staff friendly helpful good quiet location great views"
Tom 5-night trip
Posted 5 days ago
Il Chiostro del Carmine
Hotel Borgo San Luigi

Hotel Borgo San Luigi

8/10 Good
"Great breakfast and clean room. However, not a very kid friendly with no high chair available in the room and the few ones in the restaurant were broken or dirty. Good place for adulte."
Samuel 2-night trip
Posted 5 days ago
Hotel Borgo San Luigi
Hotel Minerva

Hotel Minerva

10/10 Excellent
"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."
Michael 1-night trip
Posted 8 days ago
Hotel Minerva
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."
Reid 2-night trip
Posted 9 days ago
Grand Hotel Continental Siena – Starhotels Collezione

More cheap stays in Pentolina

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
$53 nightly
$61 total
Nov 4 - Nov 5
Total with taxes and fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
$70 nightly
$80 total
Nov 5 - Nov 6
Total with taxes and fees
7.8/10 Good! (447 reviews)
Piccolo Hotel Etruria
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
$85 nightly
$97 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
$90 nightly
$103 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (109 reviews)
Albergo Centrale
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence
Hotel Massa Vecchia

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR
Get rates
8.6/10 Excellent! (11 reviews)
Hotel Massa Vecchia

Frequently asked questions

What is the best area to stay in Pentolina?
The best area to stay in Pentolina is within the historic village itself, particularly around the central Piazza della Cisterna.This area is the heart of Pentolina, characterized by its narrow, winding cobblestone streets, stone buildings, and numerous artisan shops and trattorias. The Piazza della Cisterna, with its ancient well, serves as a natural gathering point and is surrounded by charming cafes and local businesses. From here, you can easily walk to the Collegiata di Santa Maria Assunta, the village's main church, and enjoy panoramic views of the Tuscan countryside.Couples will find the historic village particularly appealing. The intimate setting, opportunities for romantic strolls through quiet alleyways, and access to local wine bars and fine dining establishments create an ideal backdrop for a relaxed getaway. Many accommodations here are renovated historic homes, offering a unique and authentic experience.Families will also appreciate the convenience of staying within the village. The pedestrian-friendly streets mean children can explore freely, and the central location makes it easy to access local gelato shops and small parks.
When is the best time to go to Pentolina?
The best times to visit Pentolina are during the shoulder seasons of April to May and September to October, offering pleasant weather and fewer crowds.During these months, the temperatures are moderate, ranging from the mid-60s to high 70s Fahrenheit (18-26°C), superb for exploring the Tuscan countryside. You'll find the landscapes lush and green in spring with wildflowers blooming, and in autumn, the vineyards are rich with color as the harvest begins. These periods allow for comfortable vineyard tours, scenic drives, and outdoor dining without the intense heat or larger tourist numbers of mid-summer.For couples seeking a romantic and tranquil escape, these shoulder seasons are particularly ideal. The cooler evenings are superb for enjoying a glass of local wine on a terrace, and the reduced crowds mean a more intimate experience at popular attractions and local eateries.
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 Pentolina.
How much is the nightly rate at a Pentolina hotel?
Prices for hotels in Pentolina often vary, but you can find a great deal from $54 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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