Castiglione della Pescaia Vacations from $837

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 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 della Pescaia Vacation

The medieval heritage, coastal scenery and family-friendly attractions are just three of the reasons why people adore this beachfront city. Discover this incredible destination in whatever way you choose with a Castiglione della Pescaia vacation package. Make your trip to Castiglione della Pescaia even more fulfilling by including some sightseeing. Golf Club Punta Ala, Port of Marina di Grosseto and Natural Reserve Diaccia Botrona are some of the leading attractions worth exploring. Your dream Castiglione della Pescaia vacation is clicks away. Explore hotels, airfares and more on Expedia for a trip that's tailored to suit your style.

The Latest Castiglione della Pescaia vacation packages

Price found within the past 48 hours. Click for updated prices.
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 $1,462, price is now $837 per person
$837
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (469 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $3,172, price is now $1,995 per person
$1,995
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (79 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.

Reviewed on Jul 5, 2025

Hotiday Room Collection - Massa Alta

Hotiday Room Collection - Massa Alta

3 out of 5
Save 100% on your flight
Price was $2,236, price is now $1,586 per person
$1,586
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
No reviews
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,760, price is now $1,003 per person
$1,003
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on Aug 19, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,484, price is now $893 per person
$893
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
The room that we used for 5 nights was filthy.and dusty. The shower was very small, barely squeeze in. The interior was outdated with only one point to recharge phones and the cupboards were broken. The door to the room required force to open and close. Location is convenient close to transport.

Reviewed on Aug 23, 2025

Don't see what you're looking for?
See all available trips from Columbus to Castiglione della Pescaia
View all trips

Discover the most popular places to visit in Castiglione della Pescaia

Punta Ala Marina

Explore the waterfront in Punta Ala with a trip to Punta Ala Marina. Discover the countryside and spas in this relaxing area.

Punta Ala Marina

Golf Club Punta Ala

5/5(1 review)

Enjoy a round of golf in Punta Ala at Golf Club Punta Ala. Stroll along the marina or discover the area's countryside.

Golf Club Punta Ala

Vetulonia Ruins

Find out about the history of Castiglione della Pescaia when you spend time at Vetulonia Ruins. Stroll along the marina or visit the spas while you're in the area.

Vetulonia Ruins

What to do in Castiglione della Pescaia

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

$41
per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
Follonica: Acqua Village Water Park Entry Ticket

Follonica: Acqua Village Water Park Entry Ticket

$30
per adult
Follonica: Acqua Village Water Park Entry Ticket
See all activities in Castiglione della Pescaia

Castiglione della Pescaia Hotel Deals

L'Andana

L'Andana

5 out of 5
Tenuta La Badiola, Castiglione della Pescaia, GR
$488 nightly
The price is $548 total per night from Sep 2 to Sep 3
$548 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (79 reviews)
"What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go."

Reviewed on Jul 5, 2025

L'Andana
Cala del Porto Punta Ala

Cala del Porto Punta Ala

5 out of 5
Via Cala del Pozzo, Castiglione della Pescaia, GR
$289 nightly
The price is $330 total per night from Sep 26 to Sep 27
$330 total
Sep 26 - Sep 27
Total with taxes and fees
10/10 Exceptional! (3 reviews)
"All staff was superb."

Reviewed on Jul 10, 2025

Cala del Porto Punta Ala
Camping Village Rocchette

Camping Village Rocchette

3 out of 5
Strada Provinciale 62 delle Rocchette, Castiglione della Pescaia, GR
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $69 total per night from Sep 26 to Sep 27
$69 total
Sep 26 - Sep 27
Total with taxes and fees
7.8/10 Good! (59 reviews)
"Lovely little Bungalow very quiet surroundings Lovey pool and quiet Restaurant very helpful when closing made us a sandwich when for back from rme at 10.30pm Shop closes a little early7.30pm if u arrive late for booking in but was friendly n helpful when they were just closing to get. Few bits"

Reviewed on Sep 28, 2019

Camping Village Rocchette
See all 529 properties in Castiglione della Pescaia
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Castiglione della Pescaia vacation package cost?
You can pick up a vacation package to this top destination from $837 on Expedia. However, how much your vacation to Castiglione della Pescaia costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Castiglione della Pescaia?
October, November and December are great times to search for cheap Castiglione della Pescaia vacation packages. Choosing to travel in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Castiglione della Pescaia?
The ideal length of your Castiglione della Pescaia vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to check out all the major sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Castiglione della Pescaia?
Castiglione della Pescaia has everything you need for a fantastic getaway — watersports, walking trails and hiking are just the start. Whether you'd like to check out sights such as Natural Reserve Diaccia Botrona and Red House of Ximenes, or venture off the beaten track, you'll have plenty to explore on your Castiglione della Pescaia vacation.
How to find the best Castiglione della Pescaia package deals?
Use Expedia's handy filters to help you find some tempting Castiglione della Pescaia package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Castiglione della Pescaia package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Castiglione della Pescaia vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a personalized Castiglione della Pescaia vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Castiglione della Pescaia?
If you have your Castiglione della Pescaia vacation dates confirmed, book as early as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Castiglione della Pescaia?

  1. Choose your travel dates: What you'd like to do in Castiglione della Pescaia and your favorite season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Castiglione della Pescaia.
  3. Organize your Castiglione della Pescaia escape with our trip planning tool: Look for and book accommodations and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Castiglione della Pescaia together.
  4. Decide your trip length: Think about how much time you want to spend exploring Castiglione della Pescaia. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Castiglione della Pescaia vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Castiglione della Pescaia's highlights. Find all the exciting things to do in Castiglione della Pescaia with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Castiglione della Pescaia vacation packages?
If you're like us, you love traveling but are not a fan of the 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 overall cost of your Castiglione della Pescaia break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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