Castellina Scalo Vacations from $684

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Your Castellina Scalo Vacation

When a city getaway is calling, answer it with a Castellina Scalo vacation package. The neighborhood of Lecchi in Chianti, which is good for walking, cycling and views, makes an awesome base for your adventures. There's plenty to include on your must-do list during a trip to Castellina Scalo, starting with leading sights such as Monteriggioni Castle and San Leonardo al Lago. Don't delay exploring this destination any longer. Your perfect Castellina Scalo vacation is a couple of clicks away with Expedia.

The Latest Castellina Scalo vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,231, price is now $684 per person
$684
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Good value for price and location.

Reviewed on Sep 8, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,435, price is now $865 per person
$865
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
We never had an opportunity to use the spa

Reviewed on Sep 8, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,137, price is now $701 per person
$701
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Right near the attractions. Easy to get around

Reviewed on Sep 4, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $4,121, price is now $2,661 per person
$2,661
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (458 reviews)
Villa Cora was delightful in every way. The only negative thing I have to say is that I am not currently still there. Alas, I would highly recommend Villa Cora as a jumping off point for your Tuscan or Firenze adventures.

Reviewed on Sep 6, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $5,021, price is now $3,268 per person
$3,268
per person
Nov 2 - Nov 8
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (3 reviews)
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Discover the most popular places to visit in Castellina Scalo

#TroveOn View of the Castle from the via francigena, while the fog leaves the valley as the sun rises. Monteriggioni is a small medieval village 12 km far from Sienna and 43 from Florence. Absolutely beautiful, the best period to visit Tuscany is from May to July.

Monteriggioni Castle

4/5(6 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.

Monteriggioni Castle

What to do in Castellina Scalo

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
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
Chianti and San Gimignano Sunset Tour

Small-Group Chianti and San Gimignano Sunset Trip from Siena

$210
per adult
Small-Group Chianti and San Gimignano Sunset Trip from Siena
See all activities in Castellina Scalo

Castellina Scalo Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $245 total per night from Oct 6 to Oct 7
$245 total
Oct 6 - Oct 7
Total with taxes and fees
Hotel Athena
Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $76 total per night from Sep 28 to Sep 29
$76 total
Sep 28 - Sep 29
Total with taxes and fees
Hotel Ristorante Alcide
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
$452 nightly
The price is $508 total per night from Sep 15 to Sep 16
$508 total
Sep 15 - Sep 16
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
See all 6,947 properties in Castellina Scalo
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.

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Frequently asked questions

How much does a Castellina Scalo vacation package cost?
Offering great value package deals from $684 on Expedia, you'll be pleasantly surprised at how much a vacation to Castellina Scalo costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Castellina Scalo?
January, September and December are great times to look for cheap Castellina Scalo vacation packages. Traveling in quieter months means you'll typically find lower prices on hotels and flights.
How many days is enough for Castellina Scalo?
Typically, a handful of days is enough to go to the top sights during your Castellina Scalo vacation. But if you prefer to have more time to relax or go on day tours, think about extending your trip.
How to find the best Castellina Scalo package deals?
Use Expedia's filter tool to find some great Castellina Scalo package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Castellina Scalo package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Castellina Scalo vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Castellina Scalo vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Castellina Scalo?
If you have your Castellina Scalo vacation dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Castellina Scalo vacation packages?
Your Castellina Scalo getaway should be an escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.