Casole d'Elsa Vacations from $965
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Your Casole dElsa Vacation
Let our vacation packages to Casole dElsa inspire your next adventure. There's lots to like about this captivating city, starting with the neighborhood of Frosini, which is great for history and culture. Make sure to do some sightseeing during your trip to Casole dElsa. Hedonistic Hiking and Archeological and Collegiate Church Museum are some top places to visit. Expedia is here to help you escape your routine. Tailor your vacation to Casole dElsa to suit your travel style, whatever that may look like.
The Latest Casole d'Elsa vacation packages
Price found within the past 48 hours. Click for updated prices.
Eden Rock Resort
$1,808
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
Aurum Firenze
Historic Centre of Florence
$1,394
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area.
Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.
Reviewed on Aug 12, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$1,771
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at La Scaletta in Florence! The hotel was extremely clean, and the staff was always friendly, welcoming, and very helpful throughout our stay.
The location is fantastic, just steps from the Ponte Vecchio, with so many great shops, restaurants, and beautiful sights within easy walking distance.
One of the things we loved most was the combination of history and modern comfort. Staying in such a beautiful historic building, surrounded by gorgeous frescoes and architectural details, made the experience feel very special, while the rooms still had a fresh, modern vibe.
The terrace bar was another highlight and a wonderful place to relax and enjoy Florence. Beautiful hotel, excellent location, and great service. We would definitely recommend La Scaletta and would happily stay here again!
Reviewed on Aug 12, 2026
Grand Hotel Cavour
Historic Centre of Florence
$1,461
per person
Oct 24 - Oct 28
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Fantastic location, lovely rooftop terrace - my only comment would be that the rooms need somewhere to sit down.
Reviewed on Aug 13, 2026
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View all tripsStay near popular Casole d'Elsa attractions
Archeological and Collegiate Church Museum
8.0/10 (1 review)
You can spend an afternoon exploring the galleries in Archeological and Collegiate Church Museum during your travels in Casole d'Elsa. Discover the beautiful countryside and wineries in this quaint area.
Terre di Vini
Enjoy an outing to Terre di Vini during your stay in Pievescola. Discover the beautiful countryside and wineries in this walkable area.
What to do in Casole d'Elsa
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
$21
per adult
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$59
per adult
88% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
$158
per adult
86% of travellers recommend
Casole d'Elsa Hotel Deals
Castello di Casole, A Belmond Hotel, Tuscany
Localita Querceto Casole d'Elsa SI
Fully refundableReserve now, pay when you stay
$1,825 nightly
$2,010 total
Aug 19 - Aug 20
Total with taxes and fees
9.6/10 Exceptional! (83 reviews)
"Once in a lifetime trip. The facilities, the staff, the rooms, the views, the activities were all exceptional."
Reviewed on Jul 29, 2026
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$338 nightly
$383 total
Aug 26 - Aug 27
Total with taxes and fees
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$173 nightly
$196 total
Aug 27 - Aug 28
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Wonderful hotel in great location just a short walk from the centre but quiet and peaceful in the evening. Fabulous helpful staff. Breakfast always fresh and lots of choice. We used the terrace restaurant once and it was fabulous - what amazing views! Highly recommended for a short or longer ..."
Reviewed on Aug 6, 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.
Find the Best Casole d'Elsa Vacation Packages
Casole dElsa Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Population | 1,000 |
Max Temp Winter | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Tenuta Torciano Winery, Monteriggioni Castle and Sovestro in Poggio Winery |
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Frequently asked questions
How much does a Casole d'Elsa vacation package cost?
You'll find cheap prices from $965 on Expedia for your Casole d'Elsa break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Casole d'Elsa costs.
What are the cheapest months to go to Casole d'Elsa?
February, October and December are the best times to search for cheap Casole d'Elsa vacation packages. Opting to travel in quieter periods means you can generally find better prices on flights and hotels.
How many days is enough for Casole d'Elsa?
Usually, a handful of days is enough to visit the top sights during your Casole d'Elsa vacation. But if you prefer to have some time to relax or take day tours, think about extending your itinerary.
How to find the best Casole d'Elsa package deals?
Begin your search for a Casole d'Elsa package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Casole d'Elsa package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Casole d'Elsa adventure underway.
Is it cheaper to book a Casole d'Elsa vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Casole d'Elsa vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Casole d'Elsa?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Casole d'Elsa getaway.
How to plan a trip to Casole d'Elsa?
- Choose when to travel: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to escape to Casole d'Elsa.
- Set your budget: Consider costs such as flights, transportation and food when calculating how much to put aside for your trip to Casole d'Elsa. Then, select a property that matches your budget, whether that's an economical option or a swankier retreat.
- Explore Casole d'Elsa using our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Casole d'Elsa. You can also save your favorite places, collaborate with friends and family and organize your plans in one place.
- Decide how long to go away for: Now that you're more familiar with Casole d'Elsa, you can work out the perfect length of your vacation. Pull together a rough plan and allocate enough time for all the things you want to do.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Casole d'Elsa vacation package that brings all your bookings together.
- Book experiences or activities ahead of time: Whether it's entrance to a major attraction or a day trip, you won't have to worry about missing out on the best Casole d'Elsa has to offer. Find all the incredible things to do in Casole d'Elsa with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Casole d'Elsa vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Casole d'Elsa vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
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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.
