
Cottage holiday rentals in Siena
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Top-rated cottage rentals in Siena
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Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Stone House with Exclusive Pool Codilungo in Chianti
Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Cottage Cappero - Masseto In Chianti
MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Il Fienile, Cottage in the country with Jacuzzi
Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Rooms sanitized by health protocols. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Country cottage C&M surrounded by greenery, love Tuscany
Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Casa La Misura in the heart of Chianti
La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

Countryside, 10 min from Siena
Apartment and large garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt road).

Chianti Independent barn
The farm was built from a characteristic 70 square metre stone barn, completely renovated and furnished with antique furniture. Panoramic view of the Chianti hills with breathtaking sunsets. From March 1 to December 31, guests will be required to pay a tourist tax of €2 per person per day. Children up to the age of 14 do not pay.

Historic Mill in the Countryside -Chianti Classico
Our house is a four centuries-old mill in the Tuscan country-side, completely restored, preserving its original image with a warm and cosy atmosphere where the old and the new perfectly meet. It is the ideal place to spend both a relaxing and cultural holiday.

Countryside Cottage With View - Le Rondini apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.
Popular amenities for cottage rentals in Siena
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

From Simone, podere santi Lucia and Pietro

Independent cottage with private spa

Luxury Cottage Spaccasole - Pool W/Cortona

Cottage in the greenery with private jacuzzi and pool

Panoramic view & outdoor jacuzzi - Pienza

"Rosso Poggiolo" farmhouse with swimming pool.

Tuscany Villa Girasole
Pet-friendly cottage rentals

Rustic retreat in the Tuscan hills

FAETOLE typical Tuscan country house near FLORENCE

Cottage in the south of Tuscany

Villetta Belvedere

Lovely apartment, pool, garden view near Siena

QuarterApartment for 6P Agriturismo Quarantallina

La Casa del Frantoiano - Pari -

Barn in Chianti
Private cottage rentals

Tuscan country house with pool

Cottage Michelangelo, green in the city

The Five Oaks Cottage

Typical Tuscan house

Chianti Loft (AC & Pool)

Loft & patio under the vineyard

Gelsomino Cottage near Firenze,San Gimignano,Sien

Glicine romantic cottage in country
Quick stats about cottage rentals in Siena

Nightly prices starting at
Siena holiday rentals start at € 137 per night before taxes and fees

Verified guest reviews
Over 90 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siena rentals

4.9 Average rating
Siena stays are highly rated by guests – averaging 4.9 out of 5!
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- Santa Maria Novella
- Mercato Centrale
- Ponte Vecchio
- Salvatore Ferragamo Museum
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Cala Violina
- Piazzale Michelangelo
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Pitti Palace
- Boboli's Garden
- Parco delle Cascine
- Palazzo Vecchio
- Medici Chapel
- Mugello Circuit
- Avignonesi Winery Fattoria Le Capezzine
- Stadio Artemio Franchi
- Palazzo Medici Riccardi
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