Siena Vacations from $1,024

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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.
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

Historic Centre of Florence
$1,024
per person
Dec 7 - Dec 12
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (75 reviews)
Hotel Duomo Firenze

Hotel Duomo Firenze

Historic Centre of Florence
$1,033
per person
Dec 10 - Dec 16
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Absolutely everything was perfect - from checkin to deprture- Gelato and cookies available all day, wonderful breakfast, room was SO Awesome facing the Duomo, assist to schedule a taxi - lift so less stairs - would absolutely recommend !!!

Reviewed on Oct 2, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

Historic Centre of Florence
$1,536
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (77 reviews)
Excellent lodging option very close to the Duomo and central to Florence. It is a terrific location in that it is close to everything but secluded off a very small road that only gets traffic for people checking in or leaving the property. The lodging is in a very old tower that has been converted to about 10 rooms. The front desk is excellent and surprised us when we checked in by telling us they would deliver an assortment of pastries to our room every day for breakfast. We had the Gemma suite which was not large but well laid out with a very comfortable bed and furniture and a very nice bathroom.

Reviewed on Oct 4, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

Historic Centre of Florence
Save 100% on your flight
$2,206
per person
Dec 7 - Dec 12
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (318 reviews)
We couldn’t have had a more enjoyable day at this fabulous hotel. The staff responded to our every whim and even anticipated some! And its location right in the center of historic Florence cannot be beat. We will be back again!

Reviewed on Oct 4, 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Cortona Old Town
$1,292
per person
Dec 12 - Dec 18
found 7 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (337 reviews)
From the moment we arrived at Monastero di Cortona, everything was wonderful. We were welcomed with a cold, delicious drink and invited to sit and relax while the staff took care of everything else for us. Anna then gave us a lovely tour of the hotel, which was such a nice way to begin our stay. When we walked into our room, there was a beautiful welcome table waiting for us with waters, chocolates, and even a lovely necklace charm, which was such a thoughtful touch. The room smelled absolutely amazing, and the view was stunning. Even the shower felt like a spa experience, with chromotherapy lighting and water that left our skin feeling incredibly soft. The complimentary breakfast was amazing, beautifully presented, and the staff was so attentive and made sure we had everything we needed. We also spent time at the spa and absolutely loved it. The Turkish bath, sauna, and massaging pool were all incredibly relaxing, and we also had massages that were absolutely amazing. Even as we were leaving, the thoughtfulness continued—the housekeeping staff left us a departing gift, which was such a sweet and unexpected touch and made us feel special right up until the end. From the beautiful surroundings to all the thoughtful little details and wonderful service, our stay felt luxurious, peaceful, and very special. We truly felt taken care of from the moment we arrived until the moment we left.

Reviewed on Oct 5, 2026

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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
A historic square with a prominent Gothic-style tower, surrounded by traditional buildings with arched windows and stone facades.

Siena City Centre

6 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.

A bustling square with historic buildings and a prominent tower.

Siena Historical Center

1 out of top 10 points of interest in this area

One of Europe’s best-preserved medieval centers is filled with references to Siena’s long and interesting artistic, intellectual and political history.

A historic square with a prominent clock tower and surrounding buildings.

Ravacciano

Though Ravacciano might not have many top sights, you can venture to the surrounding area to see attractions like Banca Monte dei Paschi di Siena and Siena State Archives.

A historic square with cobblestone pavement, a fountain, and classical architecture.

San Prospero

If you're looking for some top things to see and do in San Prospero and surrounding area, you can visit Fortezza Medicea and Fontebranda.

A historic brick archway with a circular emblem and a plaque.

Camollia

Camollia might not have many top sights, but Fortezza Medicea and Fontebranda are two attractions nearby that you can check out.

Stay near popular Siena attractions

A historic square with cobblestone pavement, surrounded by multi-story buildings with traditional architecture.

Piazza del Campo

9.6/10 (1,995 reviews)
Siena's shell-shaped Piazza del Campo pulses with medieval charm and hosts the thrilling Palio horse race twice yearly. Sip espresso at a café while admiring the soaring Torre del Mangia tower and Gothic architecture.
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A grand cathedral with intricate Gothic architecture, a prominent bell tower, and a bustling square with people.

Siena Cathedral

9.6/10 (1,693 reviews)
Siena Cathedral's Gothic façade and black-and-white marble interior display masterpieces by Michelangelo and Donatello. Visit June-October to see the extraordinary inlaid marble floor fully uncovered.
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A historic building with a statue in front.

Banca Monte dei Paschi di Siena

8.6/10 (116 reviews)
Founded in 1472, Monte dei Paschi di Siena is the world's oldest operating bank in the Gothic Palazzo Salimbeni. Visit during Palio festivals when the bank displays its Sienese art treasures.
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A historic building with a tall tower and arched windows.

Palazzo Pubblico

9.4/10 (583 reviews)
This 13th-century Gothic masterpiece houses the Civic Museum with Lorenzetti's famed frescoes of good and bad government. Climb the Torre del Mangia for spectacular views across Siena's terracotta rooftops.
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A historic cityscape with prominent architecture, including a bell tower and a cathedral.

Fortezza Medicea

9.0/10 (335 reviews)
This imposing 16th-century fortress built for Cosimo I de' Medici offers panoramic views across Siena's terracotta rooftops. Visit the Enoteca Italiana to sample Tuscany's finest wines.
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A historic square with a prominent tower and a large open space with people walking.

Torre del Mangia

9.4/10 (121 reviews)
This medieval bell tower offers breathtaking panoramic views of Siena's historic cityscape after climbing 400 steps. Reserve your morning visit to experience the Tuscan countryside in cooler temperatures.
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University for Foreigners of Siena

7.8/10 (8 reviews)
This renowned institution teaches Italian language and culture to international students. Experience academic immersion while enjoying its convenient location near Siena's medieval center and railway station.
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Siena State Archives

8.0/10 (28 reviews)
Housed in Renaissance-era Palazzo Piccolomini, the State Archives of Siena preserve documents from the 8th century. Marvel at the "Tavolette di Biccherna" – painted medieval account book covers of Siena's artistic heritage.
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What to do in Siena

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$21
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$75
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Pasta-making class at a Cesarina's home with tasting - Siena

Pasta-making class at a Cesarina's home with tasting - Siena

$207
per adult
Pasta-making class at a Cesarina's home with tasting - Siena
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Siena Hotel Deals

Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$136 nightly
$153 total
Nov 1 - Nov 2
Total with taxes and fees
Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$372 nightly
$416 total
Nov 1 - Nov 2
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Chiusarelli

Hotel Chiusarelli

Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
$118 nightly
$133 total
Nov 5 - Nov 6
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Really enjoyed our stay. Room was spacious and clean. Very nice breakfast and the staff were very kind and helpful."

Reviewed on Sep 25, 2026

Hotel Chiusarelli
See all 907 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

Things to do in and around Siena

Siena offers a rich blend of cultural, outdoor, and romantic experiences perfect for tourists. You can explore the charming streets, indulge in wine tastings, and enjoy luxurious spa treatments. Consider booking Siena vacation packages or guided tours to enhance your visit. Don't miss out on wine tour packages to savor the region's famous wines while immersing yourself in the local culture.

Shopping

Siena offers charming local shops for unique gifts and souvenirs. If you're up for a drive, The Mall Luxury Outlet, 27 miles away, and Fashion Groove, 26 miles away, provide a variety of brands and family-friendly vibes. RI Crea RE, located 24 miles from Siena, is also worth a visit.

Recreation

Experience the thrill of local sports at Siena Stadium and Stadio Artemio Franchi, both offering vibrant atmospheres. For a cultural escape, enjoy a romantic show at Teatro dei Rinnovati, where entertainment meets family-friendly vibes in a stunning setting.

Adventure

Experience the thrill of karting at Siena Circuit, located 7 miles from the city, perfect for adrenaline junkies. Hike the scenic Sentierelsa Trail, 12 miles away, to immerse yourself in nature. For an exhilarating zipline adventure, visit Saltalbero Adventure Park, situated 13 miles from Siena.

Nightlife

Siena's nightlife is charming and vibrant. Visit Il Fiaschetto, a cozy drinking pub located 26 miles from the heart of Siena, where you can enjoy romantic vibes and lively entertainment. Sip on local wines and mingle with friendly locals for an unforgettable evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Siena

Siena, Tuscany, is a charming destination perfect for culture lovers, outdoor enthusiasts, and romantic getaways. Visitors can explore historic churches, grand palaces, and lively piazzas. Key attractions include the stunning Siena Cathedral, the local province, and the Siena Stadium. With its rich cultural experiences and family-friendly activities, Siena promises an unforgettable vacation for travelers seeking to immerse themselves in Italy's enchanting history and beauty.

  • Piazza del Campo: This iconic square is the heart of Siena, renowned for its unique shell shape and vibrant atmosphere. Surrounded by medieval buildings, it's a perfect spot to soak in local culture, enjoy a coffee, or witness the thrilling Palio horse race held twice a year.
  • Siena Cathedral: A masterpiece of Gothic architecture, Siena Cathedral boasts stunning frescoes and intricate marble floors. Its striking façade and the breathtaking Piccolomini Library make it a must-see for art and history enthusiasts alike.
  • Banca Monte dei Paschi di Siena: Established in 1472, this historic bank is the world's oldest surviving bank. Its elegant architecture and rich history reflect Siena's financial importance, offering a glimpse into the city’s economic past.

Best time to go to Siena

The best time to visit Siena can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Siena falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Siena falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageSlightly Low
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No RainSunnySlightly HighSlightly High
August75.6°F (24.2°C)No RainSunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Siena

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Siena.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What is the best time to go to Siena?
The best time to go for a Siena vacation package is during June and September, which are the months with the highest demand. These periods offer pleasant weather for exploring the city's cultural attractions and enjoying outdoor activities.For travelers seeking a quieter experience with potentially lower prices, consider visiting from January to February, or in November. These months typically see the lowest demand, though some attractions may have reduced hours.
How can I save money on a Siena vacation package?
When you bundle, you can save up to 30%*. To save money on a Siena package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Siena vacation package?
A Siena vacation package lets you combine round-trip flights, hotel stays, and a rental car. Many hotels in Siena offer convenient access to the city's cultural attractions, and most provide airport shuttle service, often to Florence (FLR-Peretola) Airport. Most hotels also include free breakfast, which can be a practical saving during your trip.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Siena?
For a luxury Siena vacation package, consider a stay at Hotel Certosa Di Maggiano, a 5-star property rated 9.6 out of 10. It offers family rooms, an outdoor pool, and a restaurant, with travelers often praising the wonderful breakfast and lovely location.Couples seeking a refined experience might prefer a package built around Palazzo Patrizi Suite & Spa, a 5-star hotel rated 9.5 out of 10, which features a spa for relaxation.Another strong choice for a Siena vacation package is Relais degli Angeli, a 4.5-star hotel rated 9.3 out of 10. Travelers frequently highlight the wonderful breakfast and kind staff, making for a memorable stay.
Is Siena better suited for a beach vacation or a cultural trip?
Siena is primarily a cultural destination, renowned for its rich history and medieval heritage. A Siena vacation offers deep dives into art, architecture, and local traditions, with iconic sites like the Piazza del Campo, Siena Cathedral, and Siena State Archives showcasing centuries of influence.While Italy offers beautiful coastal areas, Siena itself is a central urban destination focused on its historic city center. Travelers seeking a beach vacation would need to plan a separate trip to a coastal region, as Siena's appeal lies in its cultural attractions and urban charm.
Is Siena a good choice for a family vacation package?
Siena is a strong choice for family vacation packages, offering a blend of cultural exploration and amenities designed for comfortable stays. Most hotels provide playgrounds and babysitting services; over half offer kids clubs, and nearly a third feature family rooms, making it easier to travel with children.For accommodations, Hotel Certosa Di Maggiano, a 5-star hotel rated 9.6 out of 10 by travelers, is a great option with family rooms, a game room, an outdoor pool, a playground, and a restaurant. Travelers praise the amazing overall experience and wonderful breakfast.Families can explore the historic Piazza del Campo or enjoy outdoor space at Fortezza Medicea, about 1 mile from central Siena, which offers a park-like setting for walks and relaxation.
Are luxury vacation packages in Siena suitable for couples?
Luxury Siena vacation packages are well-suited for couples, offering sophisticated stays with amenities like spas and fine dining. Most hotels in Siena feature spas and hot tubs, providing relaxing options for a romantic getaway.Palazzo Patrizi Suite & Spa, a 5-star hotel rated 9.5 out of 10 by travelers, offers a spa and complimentary breakfast, perfect for unwinding after a day of exploring. Another excellent choice is the Grand Hotel Continental Siena – Starhotels Collezione, a 5-star property rated 9 out of 10 by travelers, which includes a restaurant and bar/lounge, with travelers often praising the beautiful rooms and incredible breakfast.Explore luxury vacation packages in Siena and romantic vacation packages in Siena to find the perfect couples' retreat.
What luxury vacation packages are available in Siena?
Siena offers a refined experience for travelers seeking luxury Siena vacation packages, with several highly-rated hotels providing premium amenities:Browse luxury vacation packages in Siena on Expedia to compare options.
Which Siena vacation packages include a pool?
Nearly all hotels in Siena offer both outdoor and indoor pools, making it easy to find a Siena vacation package with pool access.Il Pettirosso di Siena, a 4-star property rated 8.2 out of 10, provides an outdoor pool for guests.Another option is Villa Ermellina Siena, a Tribute Portfolio Hotel, a 4-star hotel rated 8.6 out of 10 with an outdoor pool, where travelers often highlight the fantastic pool.For a highly-rated stay, Ca' Bianca Tuscany Relais, rated 9.5 out of 10, features an outdoor pool, and travelers frequently mention the lovely pool and comfortable rooms.When comparing Siena vacation packages, you can filter by pool type to find the setup that best suits your preferences.
Do luxury vacation packages in Siena include spa or wellness facilities?
Yes, luxury Siena vacation packages often feature hotels with spa or wellness facilities, though specific treatments might cost extra. Most luxury hotels in Siena offer a spa and hot tubs. Top picks include Hotel Certosa Di Maggiano, a 5-star property rated 9.6 out of 10, Palazzo Patrizi Suite & Spa, a 5-star hotel rated 9.5 out of 10, and Relais degli Angeli, a 4.5-star hotel rated 9.3 out of 10. All these properties offer spa access, and most include hot tubs.Browse luxury vacation packages in Siena on Expedia to compare.
Are airport transfers included in Siena vacation packages?
Many Siena hotels offer airport shuttle services to assist with transfers, with most properties providing this amenity. This often includes service to Florence (FLR-Peretola) Airport, the closest major airport. Transfer availability, type (shared or private), and any associated costs can vary by hotel and package, so it's recommended to confirm these details directly with your chosen hotel or package provider when booking.
What are the top things to do in Siena?
A Siena vacation offers a wealth of historic and cultural experiences within its medieval city walls:Browse and book things to do in Siena on Expedia.
Do you need to rent a car in Siena, or is public transport enough?
For a Siena vacation package, public transport and walking are generally sufficient for exploring the city center. The historic core of Siena is largely pedestrian-only, with cars strictly prohibited, making walking a necessity for navigating its charming, hilly streets. Local buses provide service within the city and to the outskirts.Most hotels offer airport shuttle services to and from Florence (FLR-Peretola), the nearest major airport, making arrival and departure straightforward. While a rental car offers flexibility for day trips to the Tuscan countryside, it's not essential for sightseeing within Siena itself. Parking is available outside the city walls, though it can be expensive.
Are Siena vacation package hotels conveniently located?
Siena vacation package hotels are generally well-located, with many properties placing you within easy reach of the city's historic center and main attractions.For example, AmiRooms Affittacamere is about a 5-minute walk from central Siena, offering quick access to the heart of the city. Villa del Sole Siena, a 3.5-star property, is also about a 5-minute walk from central Siena. If you prefer a slightly more removed stay, Hotel Certosa Di Maggiano, a 5-star hotel, is about 1 mile from central Siena.Consider your preferred level of immersion in the city's bustling core when choosing your hotel location.
Are there vacation package hotels in Siena within walking distance of restaurants and shops?
Siena vacation package hotels in the city center often place restaurants and shops within easy walking distance, allowing you to explore the city's culinary and retail offerings on foot.For example, Fonte Gaia Experience B&B, Residenza d'Epoca Le Aquile, and Palazzo Patrizi Suite & Spa are all about a 5-minute walk from Piazza del Campo, a central hub for dining and shopping. This makes it convenient to enjoy local eateries and browse boutiques without needing transportation.Always check the specific location of your chosen hotel on a map to confirm its proximity to the areas you plan to frequent.
Can I change or cancel my Siena vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Siena vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Siena vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Siena vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Siena?
To find last-minute vacation packages to Siena, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Siena vacation packages?
Free cancellation on a Siena vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Siena vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Siena getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Siena vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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