Holiday rentals near Montemaggiore Wine & Countryhouses

We found 3,961 holiday rentals — enter your dates for availability

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July 2025

August 2025

If you are looking to stay near Montemaggiore Wine & Countryhouses, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Montemaggiore Wine & Countryhouses

Showing deals for:17 Oct - 24 Oct

Exceptional

(25 reviews)

Charming Villa with swimming pool in the heart of Tuscany

Cortona

5% off

AU$2,177 per night

includes taxes & fees

Exceptional

(32 reviews)

Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

Castelnuovo Berardenga, Tuscany

14% off

AU$2,060 per night

includes taxes & fees

Exceptional

(19 reviews)

Camparone, ArcenoRentalsClub Magnificent Chianti Villa Exclusive Pool Concierge

Castelnuovo Berardenga, Provincia di Siena

14% off

AU$2,786 per night

includes taxes & fees

Exceptional

(39 reviews)

Beautifully restored 16th C farmhouse w/ exclusive pool, woodlands, olive groves

Cortona, Toscana

5% off

AU$370 per night

includes taxes & fees

Exceptional

(19 reviews)

FABULOUS 6BR HOME WITH WONDERFUL SWIMMING POOL & GARDEN IN THE HEART OF TUSCANY!

Lucignano, Tuscany

9% off

AU$1,368 per night

includes taxes & fees

Exceptional

(6 reviews)

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Cortona, Tuscany

18% off

AU$739 per night

includes taxes & fees

Excellent

(11 reviews)

Special offer Newly renovated fine detached villa with fireplace.

Castelnuovo Berardenga, Tuscany

9% off

AU$190 per night

includes taxes & fees

Exceptional

(8 reviews)

Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany

Montalcino, Siena

9% off

AU$550 per night

includes taxes & fees

Very good

(10 reviews)

Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

Gaiole in Chianti, Toscana

8% off

AU$248 per night

includes taxes & fees

Exceptional

(18 reviews)

Traditional Tuscan farmhouse with breathtaking views 19 Minutes from Montalcino

Montalcino

9% off

AU$341 per night

includes taxes & fees

Wonderful

(25 reviews)

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

Civitella in Val di Chiana, Province of Arezzo

8% off

AU$531 per night

includes taxes & fees

Exceptional

(9 reviews)

Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool

Pergine Valdarno, Tuscany

13% off

AU$185 per night

includes taxes & fees

Exceptional

(51 reviews)

Casa Rossella - ArcenoRentalsClub Romantic flat in Chianti Wifi Concierge Pool

Castelnuovo Berardenga, Province of Siena

14% off

AU$381 per night

includes taxes & fees

Exceptional

(63 reviews)

Arco al Poggio, Arceno Rentals Club, Spacious Chianti Apt, Pool, Concierge, WiFi

Castelnuovo Berardenga, Toscana

14% off

AU$538 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Montemaggiore Wine & Countryhouses

Showing deals for: 13 Oct - 16 Oct

Villa Ceppeto, Best Of Tuscany at Brand New Nest

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$222 per night

includes taxes & fees

Casa di Campagna Colline Senesi San Giovanni in Poggio - app. Twilight Siena

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$449 per night

includes taxes & fees

Holiday home with private pool, WiFi, private garden, Chianti Classico, Siena

Sleeps 6 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$424 per night

includes taxes & fees

Top rated rentals - Montemaggiore Wine & Countryhouses

Premier Host

What a Villa in Tuscany is all about.

Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and send out an excellent guide book to answer nearly all your questions.

Belinda P.

Stayed May 2025

Premier Host

Monticchiello

A wonderful quiet apartment with everything you need . Comfortable bed, good a/c, good shower, well equipped kitchen, lovely host. All uphill from the car park but that’s what you expect in a hilltop village. Excellent restaurants in the village. Not far from Pienza . And a washing machine and dryer!

Linda M.

Stayed Apr 2025

Premier Host

Beautiful stay

We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.

Murray H.

Stayed Oct 2024

Great place

A great apartment in a lovely Tuscan village. Host was extremely helpful and available at all times. Would recommend.

Sharon B.

Stayed Apr 2024

Premier Host

Fabulous in every way

Just divine location, magnificent view...friendly hosts and lovely Tuscan house. We loved our stay with our 8 month old baby!

Stephanie B.

Stayed May 2019

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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