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Sep 30 - Oct 1
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Oct 1 - Oct 2
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Our top choices for Ancaiano 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
Canada
Raman
CA $201
CA $233 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Borgo San Luigi
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.
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".

2. Hotel Executive

Hotel Executive
Scacciapensieri
United Kingdom
Susan
CA $104
CA $123 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Executive
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 swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.
A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.

3. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
Australia
Andrew
CA $182
CA $206 total
includes taxes & fees
Oct 19 - Oct 20
Villa Sabolini
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 restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.
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.

4. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Leslie
CA $139
CA $166 total
includes taxes & fees
Oct 19 - Oct 20
La Certosa di Pontignano
A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.
A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.
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.

5. Sangallo Park Hotel

Sangallo Park Hotel
Vico Alto
United Kingdom
Linda
CA $140
CA $163 total
includes taxes & fees
Oct 25 - Oct 26
Sangallo Park Hotel
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 room with a woven basket on a round table, a wooden chair, and a wooden floor.
A wooden gazebo with a thatched roof overlooking a landscaped garden with trees and a view of hills.

6. Relais Castel Bigozzi

Relais Castel Bigozzi
Monteriggioni
United States
Paul
CA $198
CA $229 total
includes taxes & fees
Oct 26 - Oct 27
Relais Castel Bigozzi
A modern hotel lobby with glass-top tables, a magazine, and a small plant.
A conference room with rows of chairs, a projector, a whiteboard, and a podium.
A modern building with a sign reading 'HOTEL SAN MARCO.'
A modern waiting area with white chairs, glass tables, and a reception desk.

7. Best Western Hotel San Marco

Best Western Hotel San Marco
Siena
United Kingdom
C.K.
CA $144
CA $167 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Hotel San Marco
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 spacious living room with a wooden staircase, a sofa, a dining table, and a radiator.

8. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
Canada
Doug
CA $222
CA $252 total
includes taxes & fees
Oct 12 - Oct 13
Relais la Costa - Dimora Storica
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 bar area with wooden bar stools, a counter with bottles, and a tiled floor.
A spacious living area with a sofa, a coffee table, and a view of buildings through large windows.

9. Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
Colle di Val d'Elsa
Canada
Sheila
CA $118
CA $135 total
includes taxes & fees
Oct 30 - Oct 31
Hotel La Vecchia Cartiera
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 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.

10. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
Canada
Frank
CA $187
CA $217 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Il Piccolo Castello
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 view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.

11. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
United States
Rita
CA $86
CA $105 total
includes taxes & fees
Oct 18 - Oct 19
Hotel Casafrassi
A modern lobby with white leather sofas, a glass coffee table, and potted plants.
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.
A modern living room with a sofa, a dining table, and a TV stand.

12. ApartHotel Anghel

ApartHotel Anghel
Siena
Netherlands
Lauro
CA $110
CA $127 total
includes taxes & fees
Oct 6 - Oct 7
ApartHotel Anghel
A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.
A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

13. Four Points by Sheraton Siena

Four Points by Sheraton Siena
Scacciapensieri
United States
Ralph
CA $210
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Four Points by Sheraton Siena
A grand entrance with a staircase leading to a white building, surrounded by lush greenery and potted plants.
A lobby with a reception desk, a large painting, a potted plant, and a patterned floor.
A spacious indoor dining area with wooden ceiling beams, green and pink upholstered chairs, and a central bar area.
A rooftop terrace with outdoor seating, including a white sofa and wicker chairs, surrounded by potted plants and overlooking a cityscape.

14. Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel
Camollia
United States
Katherine
CA $240
CA $272 total
includes taxes & fees
Oct 25 - Oct 26
Villa Ermellina Siena, a Tribute Portfolio Hotel
A table set for breakfast with a scenic view of hills and a cloudy sky.
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.
A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

15. Palazzo di Valli

Palazzo di Valli
Siena
United States
Payton
CA $216
CA $246 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo di Valli
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a window and a light fixture.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

16. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
CA $96
CA $112 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
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 large, historic building with a covered patio and a well-maintained garden.
A room with a large window offering a view of a landscaped garden with trees and a pathway.

17. Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel
Scacciapensieri
United Kingdom
Nigel
CA $240
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
Villa Scacciapensieri Boutique Hotel
A stone building with a courtyard, surrounded by lush greenery and a hillside.
A window with white curtains, a view of buildings, and greenery.
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.

18. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
Sovicille
United States
kevin
CA $300
CA $338 total
includes taxes & fees
Oct 2 - Oct 3
Relais Le Macine di Stigliano
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.
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.

19. Relais Della Rovere

Relais Della Rovere
Colle di Val d'Elsa
Australia
Robert
CA $187
CA $212 total
includes taxes & fees
Oct 30 - Oct 31
Relais Della Rovere
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.
A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.
A room with a sofa, a desk, a bunk bed, and a patterned floor.
A yellow building with stone pillars, multiple windows, and a statue in the garden.

20. Villa San Lucchese

Villa San Lucchese
Poggibonsi
United Kingdom
James
CA $134
CA $157 total
includes taxes & fees
Oct 30 - Oct 31
Villa San Lucchese
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Top Ancaiano Hotel Reviews

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."
Jodie 1-night trip
Posted 5 hours ago
Hotel Casolare Le Terre Rosse
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 10 hours ago
La Certosa di Pontignano
Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool was out of a storybook. Staff was attentive and very nice to deal with. The grounds have endless opportunities for photos at every turn. Try to explore the grounds a little - including the painters studio with is exquisite. It has only been open four months so there are a few bugs but overall, the stay was excellent. The one area they need to improve however is the food. The selections are pretty limited and the quality was not to the standard of the property. My recommendation is have the breakfast on site and lunch by the pool, but try the surrounding towns for dinner. Castellini in Chianti is a small town 15 minutes away with great choices. One Belvedere and their sister property Locanda are both within 2 kms and have high end dining. Overall I highly recommend this villa for a unique Tuscan experience."
Peter 2-night trip
Posted 15 hours ago
Fattoria di Vegi
Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"We enjoyed our stay. The pool, hotel grounds and location were truly amazing. The food was okay but we enjoyed eating off site more. The farmhouse is very quaint and charming. You can hear others in the farmhouse. It was luxurious in many ways and more basic in other ways. But all together a wonderful stay. I would recommend for sure."
Kathy 5-night trip
Posted 1 day ago
Poderi Arcangelo
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 2 days ago
Hotel Minerva
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

8/10 Good
"Staff are nice!"
GUANGMIN 2-night trip
Posted 2 days ago
Borgo Scopeto Wine & Country Relais
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 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Really enjoyed our stay. Room was spacious and clean. Very nice breakfast and the staff were very kind and helpful."
Scott 2-night trip
Posted 4 days ago
Hotel Chiusarelli
Hotel Athena

Hotel Athena

10/10 Excellent
"Excellent location with free. And easy parking. Great breakfast, extremely kind and helpful staff, small but adequate shower. Would definitely stay here in the future!!"
Lynne 3-night trip
Posted 5 days ago
Hotel Athena

More cheap stays in Ancaiano

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $82
CA $99 total
Oct 28 - Oct 29
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
CA $176
CA $201 total
Oct 1 - Oct 2
includes taxes & fees
7.8/10 Good! (442 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $207
CA $236 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
CA $103
CA $248 total
Oct 20 - Oct 21
includes taxes & fees
Castello di Bossi
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $219
CA $249 total
Oct 24 - Oct 25
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
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 Ancaiano?
The best area to stay in Ancaiano is within the historic hilltop town itself, particularly around the central Piazza della Cisterna and the surrounding narrow streets.This area offers an authentic Tuscan experience, with properties often housed in beautifully restored medieval buildings. You'll find a delightful mix of local trattorias, wine bars, and artisan shops within easy walking distance. The town's layout means you're never far from a stunning viewpoint overlooking the rolling hills of the Tuscan countryside.Couples looking for a romantic escape will find the historic centre particularly appealing. The evenings are quiet and intimate, superb for a leisurely dinner or a stroll through the lamp-lit alleys. Many accommodations here offer private terraces with breathtaking views, ideal for enjoying a glass of local wine.For those travelling with family, staying within the town walls provides a convenient and central base. Children will enjoy exploring the ancient streets and the sense of history, and you'll find it easy to pop back to your accommodation for naps or snacks.
When is the best time to go to Ancaiano?
The best time to visit Ancaiano is typically during the spring (April to June) and autumn (September to October) months.These periods offer pleasant weather, with warm days great for exploring the Tuscan countryside without the intense heat of summer. You'll find the landscapes particularly beautiful, with blooming wildflowers in spring and the rich colours of the harvest season in autumn. For those who appreciate good food and wine, autumn also brings grape and olive harvests, offering unique local experiences.Couples often find these seasons ideal for a romantic getaway. The milder temperatures are great for leisurely strolls through vineyards, cycling along quiet country roads, or enjoying al fresco dining at local trattorias. Spring and autumn also tend to be less crowded than the peak summer months, allowing for a more relaxed and intimate experience.For travellers looking for a more active holiday, spring and autumn are excellent for outdoor pursuits.
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 Ancaiano.
How much is the nightly rate at a Ancaiano hotel?
Prices for hotels in Ancaiano often vary, but you can find a great deal from CA $99 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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