Cottage vacation rentals in Province of Siena

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Top-rated cottage rentals in Province of Siena

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Guest favourite

Cottage in San Filippo A Ponzano

4.98 out of 5 average rating, 171 reviews

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.

Jan. 17 – 24

$527 CAD per night

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 108 reviews

Villa di Geggiano - Guesthouse

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Nov. 9 – 16

$763 CAD per night

Guest favourite

Cottage in Monteriggioni

4.97 out of 5 average rating, 173 reviews

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.

Feb. 16 – 23

$201 CAD per night

Guest favourite

Cottage in Vetulonia

4.96 out of 5 average rating, 115 reviews

La Dolce Vita ~ romantic retreat in quiet nature

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has six unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Oct. 8 – 15

$223 CAD per night

Guest favourite

Cottage in Sovicille

4.93 out of 5 average rating, 215 reviews

From Simone, Podere Santi Lucia e Pietro

Recently inaugurated, the property is a portion of Tuscan farmhouse with independent entrance immersed in the Sienese countryside just 10 minutes from the historic center of Siena. The apartment consists of two double bedrooms, a bathroom with shower and whirlpool, a living room, a kitchen. On request a cot for children 60*120 with protections. Outside there is a common yard. The price is to be understood for the entire apartment. Tax 1.5€/person

Sep. 21 – 28

$171 CAD per night

Guest favourite

Cottage in Ponte Feccia

4.95 out of 5 average rating, 130 reviews

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

Feb. 23 – Mar. 2

$169 CAD per night

Superhost

Cottage in Radicofani

4.84 out of 5 average rating, 110 reviews

Cottage "Girasole" in Tuscany

A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

Oct. 27 – Nov. 3

$224 CAD per night

Guest favourite

Cottage in Casole d'Elsa (SI)

4.86 out of 5 average rating, 110 reviews

Eco-house & garden on beautiful olive farm

New independent eco-house in rural setting, away from the crowds between Florence and Siena. This is an annex building on a family run olive farm surrounded by unspoilt Tuscan countryside. Plenty of shaded outdoor space, barbecue, stunning views, fantastic sunsets and big night skies. We are an official agriturismo and there are two other independent apartments on the olive farm that share the pool and private parking.

Feb. 4 – 11

$265 CAD per night

Guest favourite

Cottage in Montagnano

4.93 out of 5 average rating, 116 reviews

Charming cottage in Tuscany

Charming cottage located on a hill overlooking 360 degrees. Oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ area Inside the room with French bed, living room with sofa bed, bathroom, kitchenette and indoor and outdoor dining space. Ideal for couples and families with one/two children. Cot available

Nov. 9 – 16

$169 CAD per night

Guest favourite

Cottage in San Gimignano

4.87 out of 5 average rating, 163 reviews

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.

Mar. 29 – Apr. 5

$124 CAD per night

Guest favourite

Cottage in Colordesoli

4.93 out of 5 average rating, 147 reviews

Casa rurale openspace a San Galgano

La casa open space restaurata con stile ha un grande giardino con fruttteto e una pergolato di vite con barbecue e una vista spettacolare sulla vallata. Situata in un borgo del Comune di Chiusdino vicino all'Abbazia di San Galgano.

Sep. 24 – Oct. 1

$140 CAD per night

Guest favourite

Cottage in San Gimignano

4.95 out of 5 average rating, 126 reviews

Piccolo Cottage San Gimignano

Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. The airy home contains one tastefully-decorated double bedroom.

Jun. 18 – 25

$141 CAD per night