A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

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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 Siena 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 house with a tiled roof, a patio with a table and chairs, surrounded by trees and a grassy field.

2. 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.
$209 nightly
The price is $215
Sep 28 - Sep 29
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
A stone building with a pathway leading to it, surrounded by trees and greenery.

3. 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 stone building with a gravel path, potted plants, and a large vase with flowers.

4. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Montespertoli
Il Melograno, Chianti apartment in farmhouse for 4 people with garden
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

5. 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.

6. 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
An aerial view of a rural estate with a large building, a swimming pool, and surrounding vegetation.

7. 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 building with a gravel path, potted plants, and a large vase with flowers.

8. 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
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 Siena Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 17 hours ago
Hotel Chiusarelli

Find out more about Siena

Siena Cottages information

Number of reviews
68
Accommodation
4 Cottages
Lowest Price
$113
Highest Price
$215

Frequently asked questions

How much do cottages in Siena cost?
Prepare to pay between $113 and $215 per night for cottages in Siena. Whatever your budget, a wonderful stay is just a click or two away on Expedia. 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 Siena?
You'll find 4 cottages in Siena. No matter if you're taking a trip with the little ones or planning a getaway with close friends, Expedia will help you find the perfect property to reconnect with nature.
Are there any family-friendly cottages in Siena?
Book in to Fullino Nero and make your family vacation to Siena a memorable one. This family-friendly cottage has a 2-star rating and conveniences including laundry facilities and pillow top mattresses. After checking in and chilling out in your comfortable new digs, it's time to hit the road and start sightseeing. Monteriggioni Castle and Palazzo Pubblico are two excellent family-friendly attractions in Siena.
Why book your cottage in Siena with Expedia?
Expedia has some wonderful cottages in Siena, so start packing for an unforgettable vacation on nature's doorstep. If you have a certain budget, choose how much you'd like to spend and the preferred star rating of your property. Or take advantage of our filters to search for cottages with a pool or a hot tub. We'll help you find the right digs whatever your trip looks like.
How can I find cheap cottages in Siena?
With Expedia's filter tool, locating cheap cottages in Siena is a cinch. To find properties that'll make your wallet happy, narrow your search by budget, amenities and star rating.
What is there to do in Siena near my cottage?
No matter your interests, Siena has lots of things to keep you busy. Museo dell'Acqua, Accademia Musicale Chigiana and Basilica dell'Osservanza are on many visitors' sightseeing itineraries. You shouldn't miss Palasport Mens Sana, Porta Romana and San Spirito either. With Expedia's hotel deals in Siena, you can discover more renowned attractions like these with the cash you save.

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