Siena Vacation Packages

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Your Siena Vacation

From its highlights to its hidden treasures, this city is best experienced with a Siena vacation package. Check out places to stay in Lecchi in Chianti, which is great for walking, cycling and views. If a sightseeing tour is on the cards during your trip to Siena, swing by popular attractions like Siena Cathedral, Torre del Mangia and Piazza del Campo. Don't delay exploring this destination any longer. Your perfect Siena vacation is only a few clicks away with Expedia.

Top Siena Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,438, price is now CA $1,578 per person
CA $1,578
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Close to centre of Florence, room ok, clean

Reviewed on Aug. 28, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,632, price is now CA $1,665 per person
CA $1,665
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.8/10 Good! (1,004 reviews)
Very clean, aircon definitely welcome in summer temperatures, breakfast buffet very good. All within walkable distance of the Palazzo Vecchio and other attractions.

Reviewed on Aug. 30, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Price was CA $7,427, price is now CA $5,216 per person
CA $5,216
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (232 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug. 21, 2025

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
Price was CA $3,093, price is now CA $2,183 per person
CA $2,183
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (988 reviews)
Great staff, clean, convenient location

Reviewed on Aug. 28, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $2,535, price is now CA $1,837 per person
CA $1,837
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (905 reviews)
Loved the rooftop restaurant and the location for shops and tours

Reviewed on Aug. 24, 2025

Where to stay in Siena

Find the best Siena areas and neighborhoods for the activities you enjoy most. Learn more about Siena
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Siena City Centre

8 out of top 10 points of interest in this area

Siena City Centre is noteworthy for its historic sites, and you can make a stop at top attractions like Siena State Archives and Piazza del Campo.

Find hotels in Siena City Centre

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Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
The price is CA $293 per night from Sep 4 to Sep 5
CA $293
CA $330 total
Sep 4 - Sep 5
includes taxes & fees
Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 6 to Sep 7
CA $246
CA $279 total
Sep 6 - Sep 7
includes taxes & fees
NH Siena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
The price is CA $332 per night from Sep 14 to Sep 15
CA $332
CA $373 total
Sep 14 - Sep 15
includes taxes & fees
Palazzo Ravizza
See all 866 properties in Siena
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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Discover the most popular places to visit in Siena

Fortezza Medicea

Fortezza Medicea

Looming over the city, this fortress is a symbol of when Siena’s independence ended in the 16th century. Today, it’s a public space for exercise and entertainment.

Fortezza Medicea
Fontebranda

Fontebranda

Once a center of social and economic life, this monumental 13th-century public fountain is a snapshot of the world of medieval Siena.

Fontebranda

Santa Maria della Scala

Though Santa Maria della Scala might be what brings you to town, perhaps you'll have a chance to explore more of Siena while you are here.

Santa Maria della Scala

What to do in Siena

Torre del Mangia

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

CA $203
per adult
100% of travellers recommend
Siena and San Gimignano: Small-Group Tour with Lunch from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $104
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings

CA $136
per adult
From Siena: Chianti and Castles Tour with Wine Tastings
See all activities in Siena
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.