Val d'Elsa Vacation Packages
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Top Val d'Elsa Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Floren Hotel
Historic Centre of Florence
CA $1,579
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (267 reviews)
Fantastic location in the heart of Florence. They room was big, clean and the bed comfortable. Breakfast was great too.
Reviewed on Oct 8, 2026
Where to stay in Val d'Elsa
Find the best Val d'Elsa areas and neighborhoods for the activities you enjoy most. Learn more about Val d'Elsa
San Gimignano City Centre
6 out of top 10 points of interest in this area
San Gimignano City Centre is noteworthy for its historic sites, and you can make a stop at top attractions like Piazza delle Erbe and Piazza Duomo.
Certaldo Alto
You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.
Pievescola
Travelers enjoy Pievescola for its restaurants and museums. Consider checking out Terre di Vini while you're in the area.
Lucciana
If you're looking for some top things to see and do in Lucciana and surrounding area, you can visit Colle di Val d'Elsa Cathedral and Museo del Cristallo di Colle di Val d'Elsa.
San Filippo
While there might not be top attractions in San Filippo, you can explore the larger area and discover places like Castello della Paneretta and Castello di Monsanto.
Ready to book your vacation to Val d'Elsa?
Val d'Elsa Hotel Deals
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $154
CA $177 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (379 reviews)
"Beautiful property, nice and helping staff. We enjoy our stay ."
Reviewed on Oct 1, 2026
Hotel Toscana Ambassador
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
CA $99
CA $118 total
Oct 20 - Oct 21
includes taxes & fees
La Cisterna
Piazza Della Cisterna 23 San Gimignano SI
Fully refundableReserve now, pay when you stay
CA $126
CA $148 total
Nov 5 - Nov 6
includes taxes & fees
9.2/10 Wonderful! (662 reviews)
"The room was clean & staff at the desk was helpful with eating choices & travel options to other communities"
Reviewed on Oct 8, 2026
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.
Stay near popular Val d'Elsa attractions
Piazza della Cisterna
9.4/10 (327 reviews)
Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.
Photo by Paolo Ciafardini
Monteriggioni Castle
9.0/10 (61 reviews)
After visiting Monteriggioni Castle, make a plan to see the other sights and activities in Monteriggioni. Discover the area's beautiful countryside, or seek out its local tours.
San Gimignano Communal Palace
9.4/10 (150 reviews)
You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.
Piazza Duomo
9.4/10 (295 reviews)
Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.
Tenuta Torciano Winery
9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
Medieval Criminal and Torture Museum
9.0/10 (66 reviews)
This intriguing museum highlights the callousness of humans via displays of authentic and gruesome torture devices from around the world.
Sovestro in Poggio Winery
9.2/10 (18 reviews)
You can enjoy a tasting or tour at Sovestro in Poggio Winery during your travels to San Gimignano. Discover the area's beautiful countryside and wineries.
Vernaccia di San Gimignano Wine Museum
9.2/10 (15 reviews)
You can browse the exhibits at Vernaccia di San Gimignano Wine Museum, a museum with a storied past, during your travels to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.
What to do in Val d'Elsa
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $79
per adult
78% of travellers recommend
Frequently asked questions
How much does a Val dElsa vacation package cost?
The most affordable Val dElsa package is CA $1,337, so your dream trip can become a reality — without spending an arm and a leg. Combine flights, hotels and car rentals to tailor a package that suits your travel style.
How do I get a cheap travel package to Val dElsa?
Just think of all the awesome things you could do in Val dElsa with extra cash in your wallet. Watch your savings stack up when you bundle your hotel and airfare bookings into a Val dElsa vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 properties globally. Whether you're vacationing with the family or traveling on your own, exploring Val dElsa is better with a package.
Where should I stay in Val dElsa?
If Collegiate Church of Santa Maria Assunta is at the top of your must-see list, booking a hotel room in San Gimignano City Centre is an ideal choice.
What are the top hotels in Val dElsa?
Travelers heading to Val dElsa often make a reservation at Grand Hotel Baglioni or Hotel Spadai. These options are in Montelupo Fiorentino. Another happening neighborhood is San Gimignano City Centre. Hotel Casolare Le Terre Rosse and L'Antico Pozzo are recommended options in this part of town.
How far in advance should I book my Val dElsa vacation?
Travelers are normally able to browse international flights on Expedia within 12 months of departure. Booking last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Val dElsa travel package include?
With Expedia, you can select a combination of flights, car rentals and hotels to build your ideal Val dElsa travel package. Once you've made your booking, you can add on all the fun stuff like tours and experiences. Remember — the more you bundle, the more dollars you'll save!
What should I know before booking a Val dElsa travel package?
Bundling your bookings into a Val dElsa vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Val dElsa Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you're looking to fly to Val dElsa in coach or business class, simply select from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Val dElsa vacation package?
You can cancel your Val dElsa booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
Explore a world of travel with Expedia
- Villas in San Gimignano
- Borgo il Villino
- Agriturismo Villa Godenano
- Certaldo Hotels
- Cellole
- Residence Borgo San Lorenzo a Linari
- Villa IRIS LUXURY SAN GIMIGNANO
- Sovicille Hotels
- Castello di Fonterutoli Wine Resort
- Villa Cristina
- Certaldo Alto Hotels
- Winery Hotels in Volterra
- Contessa Ava Dei Lambardi
- Farmhouse with beautiful pool and jacuzzi
- Spa Hotels in San Gimignano
- Radicondoli Hotels
- Mili house 3 bedrooms 2 bathrooms and garage
- Hotel Wedding Venues Hotels in Castellina in Chianti
- Barberino Val d'Elsa Hotels
- Casole d'Elsa Hotels
- Monteriggioni Hotels
- B&B in Volterra
- Poggibonsi Hotels
- Isola SERENA Newly Expanded Private Luxury Villa
- Villa BELSOLE
- Siena Hotels
- Villa Dora
- 5 Star Hotels in Volterra
- Rv Parks in Berignone Forest Nature Reserve
- Volterra Hotels
- Amelia House Private Pool Casole Elsa Monti
- Colle di Val d'Elsa Hotels
- Monsanto Hotels
- Relais Santa Chiara Hotel by Double Hospitality
- San Gimignano City Centre Hotels
- Podere Palazzolo
- Castellina in Chianti Hotels
- Bellavista farm of Quercini Maurizio
- Tenuta Di Mensanello
- San Gimignano Hotels
- Panoramic castle with large pool on the walls. Ideal for weddings and events
- Lgbt Friendly Hotels in Volterra
- B&B in Castellina in Chianti
- Winery Hotels in San Gimignano
- Casa Cipressi
- Fattoria Lornano Winery
- Medici Fortress
- Visit Siena
- Visit Badesse
- San Gimignano Vacations
- Tenuta Torciano Winery
- Visit Colle di Val d'Elsa
- Siena Vacations
- Visit Volterra
- Visit Casole d'Elsa
- Casa Vinicola Luigi Cecchi
- Medieval Criminal and Torture Museum
- Volterra Vacations
- Piazza Luigi Pecori
- Visit Castellina in Chianti
- Cappella di Piazza
- Fortezza Medicea
- Rosia Vacations
- Visit San Gimignano
- Visit Lilliano
- Province of Siena Vacations
- Visit Vico d'Elsa
- Visit Cortine
- Buondonno Winery
- Visit Monteriggioni
- Piazza della Cisterna
- Cathedral of Volterra
- Avis Rental Cars in Volterra
- Car rental Siena
- Car rental Poggibonsi
- Car rentals near San Gimignano City Centre
- Car rental Monteriggioni
- Europcar Rental Cars in Volterra
- Car rental Volterra
- Convertible Car Rentals in Casole d'Elsa
- Car rental Colle di Val d'Elsa
- Car rentals near San Gimignano Pro Loco Association
- Car rental Barberino Val d'Elsa
- Car rental Certaldo
- Car rental San Gimignano
- Car rentals near Certaldo Alto
- Car rental Castellina in Chianti
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
