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

Search Siena Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$107 nightly
The price is $122
Oct 7 - Oct 8
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.
$186 nightly
The price is $191
Oct 8 - Oct 9
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

3. Pettirosso c/o Le Mascie

Pettirosso c/o Le Mascie
Sovicille
$494 nightly
The price is $496
Oct 7 - Oct 8
Total with taxes and fees
Pettirosso c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

4. Rondine c/o Le Mascie

Rondine c/o Le Mascie
Sovicille
$247 nightly
The price is $249
Oct 7 - Oct 8
Total with taxes and fees
Rondine c/o Le Mascie
A stone building with a pathway leading to it, surrounded by trees and greenery.

5. 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 house with a tiled roof, two windows, and a door.

6. The independent Capannina on the Tuscan hills

The independent Capannina on the Tuscan hills
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"The perfect Tuscan holiday, the perfect location to explore the surrounding attractions and come back to a comfortable home on the hill. Colle is very close, has everything we were looking for without the crowds. The bed is very comfortable, the bathroom perfectly set up. The kitchen has what is needed, but could do with a few more bowls, platters, spices oil. Best to bring that along.Our hosts were very friendly and with great communication.We highly recommend this beautiful little house!...
United States
Regina A.
The independent Capannina on the Tuscan hills
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

7. Apartment in Chianti with pool ID 453

Apartment in Chianti with pool ID 453
Sovicille
$370 nightly
The price is $373
Oct 7 - Oct 8
Total with taxes and fees
Apartment in Chianti with pool ID 453
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

8. Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4

Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
Sovicille
$370 nightly
The price is $373
Oct 7 - Oct 8
Total with taxes and fees
Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

9. Batticoda c/o Le Mascie

Batticoda c/o Le Mascie
Sovicille
$370 nightly
The price is $373
Oct 13 - Oct 14
Total with taxes and fees
Batticoda c/o Le Mascie
A stone patio with a table and a vase of flowers.

10. Apartment in Chianti with pool ID 3939

Apartment in Chianti with pool ID 3939
Sovicille
$370 nightly
The price is $373
Oct 7 - Oct 8
Total with taxes and fees
Apartment in Chianti with pool ID 3939
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

11. Capinera c/o Le Mascie

Capinera c/o Le Mascie
Sovicille
$494 nightly
The price is $496
Oct 7 - Oct 8
Total with taxes and fees
Capinera c/o Le Mascie
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

12. 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 rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

13. Cardellino c/o Le Mascie

Cardellino c/o Le Mascie
Sovicille
$370 nightly
The price is $373
Oct 7 - Oct 8
Total with taxes and fees
Cardellino c/o Le Mascie
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siena Hotel Reviews

Hotel Executive

Hotel Executive

10/10 Excellent
"Nice modern business hotel with spacious rooms. Mine had a balcony too. Plenty of parking on site. I ate in the restaurant which was good and reasonably priced. It’s a bit out of the way, so definitely not somewhere to explore Siena on foot by!"
Andras 1-night trip
Posted 13 hours ago
Hotel Executive

Find out more about Siena

Siena Cottages information

Number of reviews
65
Accommodation
6 Cottages
Lowest Price
$122
Highest Price
$496

Frequently asked questions

How much do cottages in Siena cost?
Prepare to pay between $122 and $496 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 6 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.

Explore a world of travel with Expedia