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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076


Bedrooms 3
Space 1,506 sq. ft.
Property type villa
Minimum Stay 4 - 7 nights


About the property





Mainly because this area offers so much that we hope guests will want to visit more than once. But also because we offer so much more than a conventional 'self catering rental'.

We think our guests should know what their stay will cost, with no hidden 'extras', so our 'fully inclusive rates cover:

- free Welcome Dinner at our favourite local restaurant, Osteria Alla Villa;

- a huge luxury WELCOME HAMPER of speciality foods & wines supplied by top quality local suppliers; as much of our COMPLIMENTARY MONTECCHIO HOUSEWINE as you wish, throughout your stay. Our COMPLIMENTARY COCKTAILS TRAY of branded spirits & liqueurs such as limoncello;

- ALL ENERGY COSTS - even logs for fires, and charcoal for the bbq;

- continuity in Fragonard toiletries, and all daily consumables(everything from dishwasher tablets to Montecchio's own olive oil!)

- all linens & towels(inc pool) with cleaning & change of linens every 3-4 days & at end of stay;

- indoor & outdoor games, as well as pool toys for the large pool(19m x 6m); DVD & Video libraries with a wide choice for all ages & tastes


The result, we think, is a truly comfortable vacation villa, that really feels like 'HOME FROM HOME", from the moment that you walk through the front door. We hope that you will be tempted to come and judge for yourselves!

Club Montecchio is equipped to a very high standard, and furnished with antiques and country furniture from Penny and James' private collection.

Club Montecchio is approached along a breathtaking 200 year old cypress tree alley. The Villa is situated on the highest point of the beautiful and historic VILLA D'ARCENO wine estate in southern Chianti.

The 2000 plus acre estate has 30 farmhouses spread amidst woodland, vineyards and olive groves. From it's stunning location, Club Montecchio has breathtaking 360 degree views, and a large pool (19x6 meter)set amid olive trees on a southfacing terrace, below the Villa.

Club Montecchio offers peace and tranquility with luxurious accomodation, in a spectacular setting. The surrounding area offers a wealth of choice, and the best in Tuscan architecture, culture, fine food and wine.Penny and James take pleasure in sharing their home,as well as their knowledge of the area, it's fine restaurants and famous wineries.

Club Montecchio is a spacious 3 bedroom, south-east facing villa with spectacular views accross the estate's olive groves and woodlands towards Monte Amiata and the Appenines.

It sleeps 6 and offers :

- a large terrace with covered pergola,ideal for breakfasting ouside while the sun rises

- groundfloor king double with ensuite showerroom

- groundfloor fourposter double with ensuite bathroom

- twin with iron bedsteads,ensuite showerroom and spectacular first-floor views to Monte Amiata(can be made up as double)

- large firstfloor saloon/lounge with magnificent 'hammer & anvil' beams & Tuscan fireplace

- Tuscan style kitchen/diningroom

- utility room with washer,ironing board & safe

- large south-east facing terrace & covered pergola

- hammock between olive trees in privacy of garden


Keywords: Luxury Vacation Homes

More Details

James Benfield
Member since: 2004
Speaks: english, french, german, italian
Response time:
Within a few hours
Response rate:
Calendar last updated:
October 19, 2017

About James Benfield

Penny & James Benfield had the good fortune to 'fall over' the best spot on the beautiful Villa Arceno wine estate as they were contemplating what to do after 30 years of living in London. Having been spoilt by a corporate lifestyle with lots of travel, it needed to be something exceptional, that indulged their enjoyment of good food & wine, in a beautiful setting,but away from developed centres of tourism.

James Benfield purchased this villa in 1998

Why James Benfield chose Siena Province

Because it's a piece of paradise:

- off the beaten track;

- in a stunning location on a hilltop, with breathtaking 360 degree views of the Chianti hills;

- in the countryside, but surrounded by picturesque villages, and just 20 minutes from the Renaissance gem of Siena;

- close to major roads, giving fast access to Florence, San Gimignano, Cortona, Perugia, Orvieto and many more "must see" places;

- and most important for self confessed "foodies", the area offers a wealth of good restaurants and quality wineries.

What makes this villa unique

Unparalleled peace & tranquility in accomodation that was purpose developed to give 'home from home' comfort & luxury. The owners' in-depth knowledge of the area, and it's amenities, probiding the 'inside track' on everything from which local restaurants are currently "hot", to where to park safely & legally in Florence.


Castelnuovo Berardenga Villa Accommodation and Amenities

Property Type:
  • villa
  • Catering available
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Included
Floor Area:
  • 1506 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 6
  • Parties/events not allowed
  • Pets considered ...
  • Please observe Villa Arceno estate 30 kpm speed limits.
  • Please keep noise to a minimum after 10pm.
Location Type:
  • Mountain View ...
  • Rural
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Computer Available ...
  • Covered Parking
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Fireplace ...
  • Free Wifi
  • Catering Available ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower
    Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - shower
  • Fragonard bathroom toiletries supplied throughout stay.
  • 3 Bedrooms, Sleeps 6
  • Bedroom 2 - 1 king
    Bedroom 1 - 1 king
    Bedroom 3 - 2 twin/ single
  • King size beds (2), Twin or Single Beds (2) - can be made-up as Double. Fragonard bathroom toiletries supplied throughout stay
  • Books
  • CD Player
  • DVD Player
  • Games ...
  • Music Library
  • Satellite / Cable ...
  • Stereo
  • Television
  • Toys ...
  • VCR
  • Video Library ...
  • Bicycles ...
  • Deck / Patio ...
  • Gazebo ...
  • Golf ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • 2 bicycles
  • Long-term Renters Welcome
Pool / Spa:
  • Communal Pool ...
Onsite Services:
  • Concierge
  • Massage
  • Private Chef
  • arboretum
  • churches
  • festivals
  • health/beauty spa
  • museums
  • restaurants
  • water parks
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • outlet shopping
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • golf
  • hiking
  • hot air ballooning
  • hunting
  • swimming
  • tennis
Nespresso machine - capsules supplied.


Exceptional! 5/5 -
(7 traveler reviews)

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average rating of 5.0 based on 7 reviews

Club Montecchio

  • 5 of 5

We were so happy to be able to return to

Oliveto at Club Montecchio after 8 years. We spent a month relaxing and sightseeing. This villa is wonderful with 3 bedrooms and 3 bathrooms with lots of indoor and outdoor space. James and Penny are extraordinary hosts. They go above and beyond to make you feel at home with all their extras. We would highly recommend this villa if you are looking for a getaway.

  • Submitted: May 28, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
Owner's Response: We get an extra kick out of welcoming returning guests, and we wre fortunate that most of our business is with repeat customers! Kris & Mike came back after 8 years, so their first stay must have left them with good memories ; they even brought family members and friends, to introduce them to Club Montecchio. They seemed to appreciate the additional items that we have added to the Welcome Hamper over the years - it is certainly enough to get guests through the first weekend of a vacation, and means there is no need to rush to the shops that first evening. That plus the unlimited House Wine, and fully stocked Cocktail Bar, allows guests to feel truly "home from home" on arrival. Don't leave it so long next time, Kris & Mike!
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Outside Albany New York

4 Weeks of Heaven!

  • 5 of 5

We selected L'Oliveto at Club Montecchio because we wanted 3 bedrooms and baths and proximity to Siena and we were impressed with the positive reviews. We have stayed at other villas in Italy and Europe but never for four weeks. It is a beautiful sitting; the villa is beautiful and spotless; it has a massive pool which is cleaned frequently; the villa kitchen is equipped with everything you need; the town of Castelnuovo Berardenga is five minutes away with a lovely old town, restaurants, gym, grocery store, butcher, wineries, and lovely welcoming people. Even closer there are two small beautiful old villages (Villa a Sesta and San Gusme) with a number of wonderful restaurants and all the charm of Tuscany. What sets Club Montecchio apart, however, more than the endless wine, olive oil etc, is the concierge service and particularly the host James. There are so many day trips to towns, sites, wineries one could take how does one decide: email James and Rita. James will tell you which chef to hire, which winery to see, which restaurant to go to and Rita will make the reservations. We went to Florence, Pisa, Lucca, San Gimignano, Montepulciano, Cortona, Montelupo, Gubbio, Colle di Valle d'Elsa, Siena and so many other great towns all from our lovely home base with advise an email away. Rita and James even arranged for a fantastic Palio experience in Sienna. The concierge service saved us time, money and the stress of stumbling for the answers ourselves...invaluable! If you have the opportunity to visit Club Mintecchio do it!

  • Submitted: Sep 7, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: th & George were so good to work with, because they trusted us for recommendations, and hence we were able to give them the benefit of having lived in this special place for 15 years. They made full use of our complimentary Concierge service, and we loved it. Do come again folks!
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Lovely spot in Tuscany! We wouldn't stay anywhere else!

  • 5 of 5

We couldn't be more pleased with our recent stay at Club Montecchio. We LOVED the surrounding area and the proximity to Siena and San Gusme. Our rental was clean, spacious and had everything we needed. We loved the free wine and alcohol provided during our entire stay and the welcome basket was VERY generous. The outdoor area is very cozy and private with lovely olive trees, a hammock and outdoor bbq and dining table. The kids had plenty of room to run and play and the views were spectacular. We will definitely be back. Wonderful property, James. Thank you!

  • Submitted: Jul 31, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: Ursula and family travel regularly, and have their own family vacation home in the US, so we are delighted that they found Oliveto up to their exacting standards. They clearly appreciated the priority that we gave to privacy, in designing and planning the layout of our rental villas, each with it's own large garden. We want to offer better quality in our rental villas, with the emphasis on generous hospitality, rather than price, as that is what we look for, when we plan rental vacations for ourselves. It is a joy when guests "get it"! Do come back Ursula, as you are sure of a warm welcome.
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Beautiful and peaceful

  • 5 of 5

We had a wonderful visit in a tastefully decorated and immaculate Tuscan villa. It was everything we had hoped for and more. The welcome basket included tasty Italian delicacies and there was a cold bottle of Prosecco waiting for us in the fridge! Linens and towels were changed midweek, toys were brought for our youngest and there really was as much wine as you could drink. Follow the suggestions for restaurants - we did and were not disappointed. I highly recommend Club Montecchio.

Date of arrival

02 July 2016

  • Submitted: Jul 27, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: It is still a joy when guests recognise the "extras" that we provide, as we believe strongly that there are people who appreciate "value" over just "price". That is why we provide our huge Welcome Hamper on arival, and stock our villas with all imaginable staples(toilet paper and bathroom toiletries, through to wood and matches for fireplaces), so that guests do not have to go shopping immediately on arrival, rather they can enjoy the free housewine and prosecco! We also provide free Concierge to help guest pre-plan their tours, cookery classes etc, and once again, they can just enjoy their time in our special place. Thank you Cree, for noticing!
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Incredible five nights in Tuscany

  • 5 of 5

From the moment we arrived, our stay at L'Oliveto was magical. Everything was as advertised on-line. The accommodations were great, the furnishings were beautiful, and the welcome basket was bountiful. We were fortunate that the owner's, James and Penny, were on-site to greet us. They were very gracious and full of wonderful suggestions for sightseeing and dining. We enjoyed excellent meals in the surrounding hill towns, visits to local wineries, and always looked forward to returning to our wonderful villa. It was a relaxing stay between our visits to Rome and Florence. Our only regret is that we only had five nights. We will remedy that next time.

Date of arrival

14 April 2016

  • Submitted: Jul 24, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: Owner's Response: What a joy it was to have James and group with us, and we'd love for them to return. They are experience travellers, who travel together regularly, and had planned a month long progarmme to see something of the best of Italy, and, in truth that is what it needs, because there is so much to see and experience. If you can't allow that much time, then better to concentrate on one or two places. Obviously we'd like Club Montecchio and Tuscany to be top of the list, because we really enjoy helping our guests to get the the insider's view of this magical area.
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Santa Ana, CA

Perfect Stay in Tuscany

  • 5 of 5

We rented the Oliveto villa for one week and it was perfect for us (two couples). We were welcomed by beautiful music playing and by Cristina, who gave us a thorough orientation. James came by a few minutes later to make sure we had everything we needed and make suggestions for wineries, restaurants and places not to be missed. We drove in from Le Spezia and arrived at 6pm, so the welcome basket, full of provisions for dinner, breakfast, lunch and snacks was a much appreciated touch! Lovely bottles of wine were plentiful to enjoy sitting outside watching the sunset. The villa was centrally located and we were able to make day trips to Siena, San Gimignano, Montalcino, Pienza and Montepulciano. We worked with Rita, the concierge, to take cooking lessons with Emily. She came to the villa with all the ingredients, equipment and skills to teach the four of us how to prepare a delicious Italian meal. We are grateful to James and his entire staff for their hospitality! We would return in a heartbeat!

  • Submitted: Jul 24, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: Owner's Response: This lovely group of guests arrived at Club Montecchio as part of of well planned tour of some of the best parts of Tuscany. It is a joy to read that they found Montecchio "as advertised" ie in a central location and ideal for day trips to the "must see" towns and villages; within easy reach of top notch eateries and famous wineries; supplied with a generous welcome hamper of quality foods and treats to forestall the need to go shopping on arrival; with continuous supplies of top quality housewine and a well stocked cocktail tray; in short all that is essential for a taste of la dolce vita! Our complimentary Concierge provided by a 5 star hotelier, is just another thing that we provide to be sure guests get the most out of their time with us, by allowing them to plan visits, tours, restaurant bookings ahead of time.
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Nearest Airport
100 Kilometres
Florence and Pisa
Nearest Barpub
2 Kilometres
Sira & Remino in San Gusme
Nearest Ferry
140 Kilometres
Nearest Golf
35 Kilometres
La Bagnaia in Val di Chiana
Nearest Train
20 Kilometres
Nearest Motorway
7 Kilometres
Siena-Arezzo Highway; Castelnuovo Berardenga exit
Nearest Restaurant
2 Kilometres
La Porta del Chianti in San Gusme for fish
Nearest Ski
145 Kilometres
Nearest Beach
100 Kilometres
Punta Ala and Castigline Del Pescaia
Car: necessary

Go-Karting, Thermal Spas, Shopping-Designer Outlets, Wine Tours,Cookery Schools.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Weekly rates include Welcome Dinner, luxury Welcome Hamper(enough food for first couple of days), free Cocktail Bar, unlimited free top quality Montecchio House Wine & Olive a Oil, ALL energy costs, all daily consumables(everything from toilet rolls to tissues and candles for the dining table), clean & change of linens(inc pool towels) every 3-4 days, free 5 star Concierge supplied by local hoteliers, free High Speed WIFI.
Daily, Monthly, Winter and Standard rates exclude Welcome Hamper and Cocktail Bar, available for £350 supplement.
Well behaved dogs welcome, if pre-advised.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.