Castiglione d'Orcia Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Castiglione dOrcia Vacation

The rich history and spectacular views are just the beginning of the things Castiglione dOrcia has to offer. Experience the best parts of this city your way with a tailor-made Castiglione dOrcia vacation package. Want to start exploring your surroundings? Pienza Cathedral, Palazzo Piccolomini and Abbazia di SantAntimo are a few of the top places to visit during a trip to Castiglione dOrcia. Don't delay your visit to this destination any longer. The perfect Castiglione dOrcia vacation is a couple of clicks away with Expedia.

Top Castiglione d'Orcia Vacation Deals

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

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 23
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
7.8/10 Good! (479 reviews)
We loved the location close to the Arno River and the city center. Had a delicious pizza around the corner and there is also a small grocery store for last minute necessities and water! The staff was very kind, and the breakfast was delicious. They offer free luggage storage which was convenient. Within walking distance from the main train station. We loved our stay and will be back!

Reviewed on Jun. 27, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
Great service esp Fillippo and Daniel at the breakfast service

Reviewed on Jul. 6, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 17 - Sep 23
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (464 reviews)
Nice hotel, very clean, a little far from main attractions, but in general I really like it

Reviewed on Jul. 14, 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
per person
Sep 6 - Sep 12
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (382 reviews)
Incredible off-season stay. The breakfast each morning was incredible. So much better than any other hotel I’ve stayed at. Fresh and delicious. The staff were friendly and helpful and our room was amazing. The Villa itself is a renovated Renaissance property and all around are little reminders of its glorious past. We were too early for the pool (starts in June) but I have a feeling that’s why we got such a great deal. The views from the decks are incredible and it’s close to Florence. The roads are windy and narrow, so be careful! But one of the roads down from the Villa revealed a spectacular view of Florence. I can’t recommend this hotel enough. Would gladly return.

Reviewed on May 31, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
10/10 Exceptional! (215 reviews)
From start to finish, this hotel was truly excellent. We had such a peaceful stay here, we loved the staff, the room and the breakfast!

Reviewed on Jul. 10, 2025

Ready to book your vacation to Castiglione d'Orcia?

 

Choose your dates

Castiglione d'Orcia Hotel Deals

Hotel Osteria Dell Orcia

Hotel Osteria Dell Orcia

4 out of 5
Podere Osteria 15, località Bagno Vignoni, Castiglione d'Orcia, SI
The price is CA $330 per night from Jul 22 to Jul 23
CA $330
CA $372 total
Jul 22 - Jul 23
includes taxes & fees
9.4/10 Exceptional! (46 reviews)
"Amazing personnel always taking great care of you, the place is 20 min. Drive from Montalcino, has well maintained pool, breakfast very good, laundry available and restaurant in site. Self-parking area. Great location if you want to disconnect and enjoy breathtaking views of the Tuscany area."

Reviewed on May 27, 2025

Hotel Osteria Dell Orcia
Rocca d'Orcia Suites and Villas

Rocca d'Orcia Suites and Villas

Piazzale Aleardo Monaci 13, Castiglione d'Orcia, SI
The price is CA $182 per night from Jul 17 to Jul 18
CA $182
CA $207 total
Jul 17 - Jul 18
includes taxes & fees
5/10 (2 reviews)
"Fantastic views, great outdoor space and superb service. Only negative was a very small shower in a large bathroom, why?"

Reviewed on May 29, 2025

Rocca d'Orcia Suites and Villas
Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

5 out of 5
Via della Follonata, SP Saturnia, Manciano, GR
Fully refundableReserve now, pay when you stay
The price is CA $514 per night from Jul 28 to Jul 29
CA $514
CA $566 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (411 reviews)
Rejuvenated!
"Overall, we had a fantastic stay. It was a wonderful way to celebrate my birthday. The food was pricey but delicious. They had a great spread for breakfast and we left every meal full and happy. We also had a couples massage that was wonderful. They really listened to our preferences and gave great ..."

Reviewed on Jul. 1, 2025

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World
See all 4,855 properties in Castiglione d'Orcia
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Castiglione d'Orcia

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

CA $143
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montalcino, Montepulciano & Pienza day tour from Florence

Montalcino, Montepulciano & Pienza day tour from Florence

CA $147
per adult
86% of travellers recommend
Montalcino, Montepulciano & Pienza day tour from Florence
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

CA $367
per adult
100% of travellers recommend
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
See all activities in Castiglione d'Orcia

Frequently asked questions

How much does a Castiglione d'Orcia vacation package cost?
You'll find cheap prices from CA $1,631 on Expedia for your Castiglione d'Orcia escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Castiglione d'Orcia costs.
What are the cheapest months to go to Castiglione d'Orcia?
The off-season is the best time to travel to Castiglione d'Orcia if you're trying to save. Another tip for getting cheap Castiglione d'Orcia vacation packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Castiglione d'Orcia?
The ideal length of your Castiglione d'Orcia vacation depends on what you'd like to do and see. Generally, a few days to a week will give you plenty of time to check out all the major attractions and explore some hidden treasures along the way.
How to find the best Castiglione d'Orcia package deals?
Bagging a cheap Castiglione d'Orcia package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Castiglione d'Orcia package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Castiglione d'Orcia vacation as a package?
You can enjoy significant savings on your Castiglione d'Orcia escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Castiglione d'Orcia?
Land fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Castiglione d'Orcia escape.
How to plan a trip to Castiglione d'Orcia?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Castiglione d'Orcia.
  2. Budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Castiglione d'Orcia.
  3. Set the duration of your trip: Start by compiling a list of the attractions you want to get to in Castiglione d'Orcia. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Castiglione d'Orcia vacation package.

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