Club Montecchio

San Gusme, Siena

You'll slide into holiday mode with alarming ease here in the undisturbed Sienese hills with plenty of delicious food and glorious Chianti


4 beds


3 bedrooms


Sleeps 6


A warm, spacious and very private feeling house which perches on a gentle hill. The approach is pure cinema: a straight road edged with stately cypresses dips and rises dramatically, views are over olive trees and undulating vineyards – you’re on holiday already! This is a munificent place too with a complimentary dinner on arrival and lavish welcome basket: as much local wine as you want, pasta, chocolate, local cheese, fresh tomatoes, cold meats, nibbles and delicious biscuits; there are plenty of excellent restaurants near when you’ve polished off that lot. You can hike from the door, visit exquisite villages and important Sienese Chianti vineyards and cellars, jump on a horse or organise a hot air balloon ride for wonderful views. However, there’s much comfort here so you may not want to budge, and idle souls will find themselves snoozing in a hammock, seeking shade to read one of the many interesting books here or sunning themselves on a lounger. There’s a big shared pool too for watery fun. Owners Penny and James (here for part of the year) wanted to create a home from home and they have. Spoiling.


  • Hot tub
  • WiFi
  • Swimming pool
  • Mobile reception
  • Oven
  • Open fire / woodburner
  • Hob
  • Parking on premises
  • Barbecue
  • Free parking nearby
  • Meals available
  • Paid parking nearby
  • Breakfast available
  • Accessible by public transport
  • Central heating
  • Wheelchair access
  • Limited mobility
  • Air conditioning
  • Washing machine
  • Garden
  • Television
  • Tennis court
  • Pets welcome

Family friendly

  • Baby monitor
  • Children welcome
  • Books and toys
  • Babies welcome
  • Stair gates
  • High chair


  • Pub/bar within 3 miles
  • Restaurant within 3 miles
  • Shop within 3 miles


  • Bikes available
  • Food courses
  • Kayaking
  • Other courses
  • Sailing
  • Surfing
  • Wild swimming

& pricing

Booking information

Check in
Check out
Booking restrictions
Pets by arrangement.
No smoking
Smoking not permitted anywhere in the property.
This property is part of a working farm or vineyard.
Owner has pets
Animals living on the property.
Restaurants 5-minute drive.


Nightly price
from €220
Weekly price
from €1400
Damage deposit
Extra child bed/cot available free of charge.
1 House for 6
From €2204 beds3 bedrooms


We have fallen in love with this beautiful and breathtaking part of Tuscany and have had numerous return visits. Penny and James truly are perfect hosts. The attention to detail in both the villa and the service provided are exceptional. The welcome hamper is hugely generous, the limitless house wine is sensational and the housekeeping superb. We have two youg children whom adore Montecchio and the fact that every household necessity is provided really aids the baggage allowance! I cannot recommend this enough as your perfect holiday destination. Thank you Penny and James.

Emily, Southampton

A return visit after our splendid holiday in 2016. This venue is just so relaxing and the standard and variety of the restaurants in the area means that even though the house is excellently equipped you tend to eat out! With temperatures in the upper 30C's the pool was very welcome. New garden lights had been installed since our last visit which improved the star-gazing even further. Great memories......!

Nick, Maidstone

Amazing house in an amazing location. We had previously visited Montecchio in July but this year decided to go in early May and we couldn’t believe the amount of wildlife we saw; hares, deer, pheasant, a toad and even a wild boar. This truly is a home from home with everything you could possibly need for a relaxing break or a memorable family holiday. Penny and James are fantastic hosts providing restaurant recommendations, helping arrange wine tours and even advising on the best places to park in Florence and Siena - not forgetting the limitless house wine. Thank you, we will be back!

Katherine, London

What a gem! I have stayed here a number of times and cannot fault it. Not only is the location idyllic in that it is beautiful and quiet, but everything you need is available at the house. We have stayed here as a couple, with friends and again with our baby in tow, and it has been perfect on all occasions as it is so well equipped with for all circumstances. Not only this, but we love that although we are out in the countryside, a short drive away are quaint Italian villages we can pop to, or if we want to drive a bit further then Siena and Florence are still close for day trips. Perfect!

Rachel, Kent

Montecchio, not just a great place to stay but also 'an experience'. Holidays are short and getting to know an area takes time but James quickly points out the 'gems' in the area so you can quickly become immersed in the traditions and customs of the area/region. Nothing was too much trouble and the house is excellently maintained and furnished in an tasteful, artistic and comfortable manner. The house is on the top of a hill in the middle of a wine estate so plenty of walking, gorgeous sunsets sitting by a fire pit, star gazing with minimal light pollution and drinking the house wine!

Nick, Evesham

What more could you want? Charming hilltop location on a private estate with breathtaking views over vineyards & olive groves. A decent sized swimming pool 50 yards from the front door. Spacious & well equiped accommodation & a welcoming host. Would happily recommend to one & all!

Gavin, Leamington spa

Heaven. I think that sums up Montecchio. Every detail of the property is so well thought out, you'll want for nothing, I would say a home away from home, but it's actually far better than my home! The views are incredible and we spent much of our time just lazing by the pool, looking out across the hills. We had one cloudy day and chose to visit Rapolano terme, which I highly recommend. There are also many fantastic restaurants nearby from fine dining at La Bottega del 30 to more rustic (but equally delicious) local restaurants such as Osteria Alla Villa. We are returning this year!


Paradise! Fantastic house furnished in traditional Tuscan style, with a whole host of little luxuries that make it feel special. Penny and James have thought of everything including restaurant recommendations, complimentary house wines, wifi, BBQ facilities and more. The perfect place to relax and discover the hidden gems of Tuscany. We will be back soon!

Becky, Birmingham

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The neighbourhood

Local points of interest from James Benfield

  • Villa D'Arceno estate is special, even in Bella Toscana. Rolling Chianti hills, manicured vineyards punctuated by iconic cypress alleys & ancient monuments; an enchanted fairyland, where time has slowed to help you relax! New video on our website.
  • Nearby San Gusme is a leading candidate for Chianti's prettiest walled village, with 3 restaurants, several bars, charming general store cum cafe, PO and ATM. In September the Festa del Luca celebrates the legend of a local innkeeper, with a comic history.
  • Villa a Sesta, another pretty borgo surrounded by vineyards, has breathtaking views to Siena ; watch the sunset behind the city towers with aperitivi! This is Chianti "Foodie Central" with 4 excellent restaurants, including Michelin star Bottega del 30.
  • The entrance to the Villa Arceno estate is on the famous Chiantigiana(Chianti Way). For a day of wine tasting and beautiful scenery, follow the road into the Chianti hills, as it meanders past famous name wineries like Felsina, Brolio and Fontodi. Cin cin!
  • Why a Club? Because we want guests to feel they “belong” and have found their Tuscan “home from home”. Plus we include far more than regular self catering rentals; Concierge, Welcome Meal, Welcome Hamper, Cocktails, Housewine & more. See video on website.
  • With routine sightings of deer, wild boar, red squirrel, hare, foxes and even porcupine, Villa Arceno estate's strictly controlled hunting reserve makes for a nature lover's paradise. Recent guests counted 32 bird varieties from their sun loungers!