A vineyard with rows of grapevines, rolling hills, and distant buildings.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Poggibonsi cottages

A stone building with a rustic entrance, a small patio area with outdoor furniture, and a wooden fence in the foreground.

1. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (55 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$99 nightly
The price is $113
Sep 27 - Sep 28
Total with taxes and fees
Fullino Nero
A stone building with a pathway leading to it, surrounded by trees and greenery.

2. Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"Maurizio was an excellent host, he was very helpful in explaining the house and amenities during the check in process, and also sent us a lot of references for food shopping, restaurants, wineries and things to do while in Tuscany.I highly recommend this property."
United States
Guillermo A.
Casa il Cipresso, in the heart of Chianti with swimming pool
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

3. La Misura, cottage with garden and swimming pool on the hills of Chianti

La Misura, cottage with garden and swimming pool on the hills of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti
A stone building with a small entrance, a chimney, and a view of green hills.

4. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
A stone building with a gravel path, potted plants, and a large vase with flowers.

5. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Montespertoli
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
United States
Mark S.
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
An aerial view of a rural estate with a large building, a swimming pool, and surrounding vegetation.

6. Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...
United States
Lisa S.
Casa Antico Roseto - cottage with swimming pool
A stone house with a tiled roof, a patio with a table and chairs, surrounded by trees and a grassy field.

7. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (3 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
$208 nightly
The price is $214
Sep 26 - Sep 27
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Poggibonsi Hotel Reviews

Casale di Villore

Casale di Villore

10/10 Excellent
"Our stay in the Cardisco apartment at Casale di Villore was absolutely wonderful. The location is simply stunning, with breathtaking views and the most divine infinity pool, easily one of the highlights of our stay in Tuscany. The apartment was spotlessly clean, and Alice was a fantastic host, welcoming, friendly and always happy to help. We particularly loved having our own designated sun lounger space, which made relaxing by the pool even more enjoyable. The location is also perfect for exploring the Chianti region, with beautiful vineyards and charming towns nearby. We highly recommend visiting La Croce just up the road for some lovely wines. A truly special place to stay, and somewhere we would happily return to."
Roseanne 3-night trip
Posted 5 days ago
Casale di Villore

Find out more about Poggibonsi

Poggibonsi Cottages information

Number of reviews
68
Accommodation
7 Cottages
Lowest Price
$113
Highest Price
$214

Frequently asked questions

How much do cottages in Poggibonsi cost?
Cottages in Poggibonsi range between $113 and $214 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Poggibonsi?
Claim your vacation time and pick from 7 cottages in Poggibonsi. Hoping to find a place where you can relax and connect with nature? Expedia will help you find your ideal retreat in a few quick clicks.
Why book your cottage in Poggibonsi with Expedia?
Reserving a cottage in Poggibonsi is as simple as clicking on your travel dates and choosing an ideal place for a getaway in the outdoors. From high-end retreats to inexpensive stays and cottages that come with amenities like a kitchenette, Expedia has something for all styles and tastes. As for unbeatable deals? We've got your back!
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What is there to do in Poggibonsi near my cottage?
Whatever you love to do, Poggibonsi has plenty to keep you going. Fountain of Fate, Church of San Lorenzo and San Lucchese Convent are on many travelers' trip plans. You shouldn't miss Magione Castle, Poggio Imperiale Fortress and Archeodromo di Poggibonsi either. With Expedia's hotel deals in Poggibonsi, you'll be able to see even more terrific attractions like these with the cash you save.

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