Siena Vacations from $934

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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.

The Latest Siena vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Grifone

Hotel Grifone

4 out of 5
Campo di Marte
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8/10 Very Good! (120 reviews)
Friendly staff, convenient location, great room. Highly recommended!

Reviewed on Jul 19, 2025

Hotel Datini

Hotel Datini

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8/10 Very Good! (260 reviews)
The rooms are spacious and beds are comfy. Bathroom is awesome and has everything you need. You have breakfast included and it is amazing. Bus station is right behind the hotel and you can go anywhere from there. The staff are very kind.

Reviewed on Jun 16, 2024

Starhotels Vespucci

Starhotels Vespucci

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8.4/10 Very Good! (520 reviews)
We had a wonderful stay at Starhotels Vespucci. The rooms were clean, comfortable, and well-equipped. The staff was friendly and professional, always ready to help. Breakfast was delicious with a good variety. Convenient location for both business and leisure. Highly recommended!

Reviewed on May 21, 2025

Hotel President

Hotel President

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
7.6/10 Good! (210 reviews)
No AC in April as they turn it ON from May onwards?

Reviewed on May 2, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
Very well connected. Room size Good for Family of 4. AC was not very efficient in room, Kind of slow. Rest ok Even breakfast included which is good for wallet

Reviewed on Jul 25, 2025

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Where to stay in Siena

Find the best Siena areas and neighborhoods for the activities you enjoy most. Learn more about Siena
Palazzo Tolomei showing heritage architecture and street scenes as well as a small group of people

Siena City Centre

8 out of top 10 points of interest in this area

Surrounded by photogenic Tuscan hill vineyards and villas, this enchanting medieval center features ancient ramparts, gourmet restaurants and artistic masterpieces.

Find hotels in Siena City Centre

Discover the most popular places to visit in Siena

Piazza del Campo which includes street scenes and a square or plaza

Piazza del Campo

Sit at a café and experience the atmosphere of Siena’s main square, known for its medieval architectural grandeur and famous horse races.

Piazza del Campo
Siena Cathedral which includes a church or cathedral, street scenes and heritage architecture

Siena Cathedral

Breathtaking masterpieces by some of the finest Italian artists of the Renaissance era decorate this grandiose 800-year-old religious complex.

Siena Cathedral
Palazzo Pubblico featuring a city, heritage architecture and night scenes

Palazzo Pubblico

Palazzo Pubblico is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the area's beautiful countryside, or seek out its local tours.

Palazzo Pubblico

What to do in Siena

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Siena & San Gimignano Day Trip from Florence with Chianti Views

$89
per adult
88% of travellers recommend
Siena & San Gimignano Day Trip from Florence with Chianti Views
From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings

$100
per adult
From Siena: Chianti and Castles Tour with Wine Tastings
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$76
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Siena

Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$142 nightly
The price is $162 total per night from Aug 10 to Aug 11
$162 total
Aug 10 - Aug 11
Total includes taxes and fees
9.2/10 Wonderful! (1,012 reviews)
"Staff was incredible - 10 minute walk to everything. Highly recommend! Especially loved front desk crew and Robert in the restaurant."

Reviewed on Jul 29, 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $135 total per night from Aug 3 to Aug 4
$135 total
Aug 3 - Aug 4
Total includes taxes and fees
8.2/10 Very Good! (992 reviews)
"We just need a mirror in the room to see your entire body please urgent . Other than these is the perfect hotel to stay in Lake Como area"

Reviewed on Jul 21, 2025

NH Siena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $113 total per night from Aug 3 to Aug 4
$113 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (680 reviews)
"Sunset from the garden in company with a resident turtle was amazing. Breakfast buffet was good. Hotel clean. Elevator! Staff very helpful. Easily walkable location. Would stay here again!!"

Reviewed on Jul 29, 2025

Palazzo Ravizza
See all 859 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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Frequently asked questions

How much does a Siena vacation package cost?
Offering great value package deals from $934 on Expedia, you'll be pleasantly surprised at how much a vacation to Siena costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Siena?
If you're looking to book a cheap Siena vacation package, consider planning a trip in November, December and January. You're likely to find lower rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Siena?
With around 2 days, you'll have enough time to experience popular neighborhoods such as Siena Historical Center and Siena City Centre during your Siena vacation. Be sure to also add Civic Museum and Museo dell'Opera del Duomo to your sightseeing itinerary. Looking for more adventures? Consider exploring outside of Siena on day trips and tours.
Is it worth booking a vacation package to Siena?
Whether you'd like to explore key attractions such as Siena Cathedral and Torre del Mangia on your Siena vacation, or coming for its excellent history, culture and family-friendly attractions, there's something for everyone here. With so much to do, you'll soon discover why so many people think Siena is a good vacation destination.
How to find the best Siena package deals?
Bagging a cheap Siena package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Siena package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Siena vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can personalize your Siena escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Siena?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Siena getaway.
How to plan a trip to Siena?

  1. Choose your travel dates: What you'd like to do in Siena and your favorite season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Siena.
  3. Explore Siena with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Siena. You can also save your favorite places, collaborate with friends and family and manage all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Siena, you can work out the perfect length of your vacation. Create a rough plan and give yourself enough time to cover everything you want to do.
  5. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Siena vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on Siena's highlights. Find all the exciting things to do in Siena with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Siena vacation packages?
Jet off on your ideal getaway to Siena with our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.