Siena Vacations from $1,068

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,556, price is now $1,068 per person
$1,068
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
Great place very clean and the staff were great very helpful and couldn't do enough for you nothing was too much trouble highly recommended. Would see defo go back.

Reviewed on Oct 31, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $4,947, price is now $2,826 per person
$2,826
per person
Dec 11 - Dec 17
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (3 reviews)
The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,574, price is now $1,733 per person
$1,733
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 2025

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Save 100% on your flight
Price was $5,906, price is now $4,107 per person
$4,107
per person
Dec 11 - Dec 17
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (66 reviews)
Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal.

Reviewed on Aug 3, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $1,554, price is now $1,101 per person
$1,101
per person
Dec 11 - Dec 17
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (244 reviews)
Wow best experience, fantastic service, awesome staff, beautiful room and cortona is very impressive

Reviewed on Oct 29, 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

5/5(371 reviews)

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

5/5(349 reviews)

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

5/5(133 reviews)

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

Medieval Centre

Skip the Line: Siena Duomo and City Walking Tour

$47
per adult
100% of travellers recommend
Skip the Line: Siena Duomo and City Walking Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

$57
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Siena

Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $102 total per night from Nov 27 to Nov 28
$102 total
Nov 27 - Nov 28
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
The staff was excellent and very attentive. They showed us the are and helped with finding stores and locations to visit in the area. The room and view was great. The restaurant and bar were nice and we felt entertained staying at the hotel for the evening. The breakfast Buffett in the morning was ...

Reviewed on Oct 27, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $106 total per night from Nov 10 to Nov 11
$106 total
Nov 10 - Nov 11
Total with taxes and fees
9.2/10 Wonderful! (735 reviews)
Beautiful quaint hotel. Beautiful view from the garden. Walkable to all of the sites and restaurants, at the top of the hill- but everything is on a hill. Nice breakfast. Very relaxing place to stay. Staff was very accommodating.

Reviewed on Oct 23, 2025

Palazzo Ravizza
Borgo Grondaie

Borgo Grondaie

3 out of 5
Strada delle Grondaie, 15, Siena, SI
Fully refundable
$84 nightly
The price is $96 total per night from Nov 9 to Nov 10
$96 total
Nov 9 - Nov 10
Total with taxes and fees
9.6/10 Exceptional! (436 reviews)
Safe and quiet area. About a 20 minute walk to the heart of Siena. The room felt very Tuscan with more space than expected, the property was very nice as was the pool. We didn't have breakfast included with our "apartment" but it looked great. Major grocery store just a couple minutes drive ...

Reviewed on Oct 28, 2025

Borgo Grondaie
See all 867 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.

Find the Best Siena Vacation Packages

Siena Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
42,900
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Siena Cathedral, Monteriggioni Castle and Castle of Brolio

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Frequently asked questions

How much does a Siena vacation package cost?
Offering great value package deals from $1,068 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.