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Our top choices for Castelfalfi hotels

Hotel Il Castello

Hotel Il Castello
Certaldo Alto
9.6 out of 10, Exceptional, (7)
"What a great little hotel! The town is rather small and not much shops like San Gimignano, but this hotel is clean, rooms are roomy and the garden dining is out of this world. Beautiful with views of the sunset and amazing food. One of my favorite. The town has several restaurants too and some good museums. "
United States
Thomas
$127 nightly
The price is $146
Dec 29 - Dec 30
Total with taxes and fees
Hotel Il Castello

Calzaiolo

Calzaiolo
2.0 star property
San Casciano in Val di Pesa
8.2 out of 10, Very Good, (16)
"Clean and friendly staff. Public transportation is very poor, need to rent a car if you want to be mobile."
United States
Hang
$72 nightly
The price is $81
Jan 8 - Jan 9, 2026
Total with taxes and fees
Calzaiolo

Agriturismo Podere Diacceroni

Agriturismo Podere Diacceroni
Peccioli
9.4 out of 10, Exceptional, (20)
"It was an incredible stay! The staff were so polite and personable. "
Canada
Lynn
$137 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
Agriturismo Podere Diacceroni

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (57)
"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
$112 nightly
The price is $128
Dec 25 - Dec 26
Total with taxes and fees
Relais Poggio Borgoni

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Hotel Portavaldera

Hotel Portavaldera
3.0 star property
Peccioli
8.8 out of 10, Excellent, (42)
"Great hotel "
United States
Clara
Hotel Portavaldera

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
$134 nightly
The price is $153
Jan 23 - Jan 24, 2026
Total with taxes and fees
Villa il Fedino

Villa il Poggiale - Dimora Storica

Villa il Poggiale - Dimora Storica
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (145)
"Wonderful stay."
United States
Nancy
$112 nightly
The price is $124
Jan 14 - Jan 15, 2026
Total with taxes and fees
Villa il Poggiale - Dimora Storica

Le Mammole

Le Mammole
San Miniato
9.8 out of 10, Exceptional, (24)
"Cozy and quiet place in the midst of nature. Host was extremely welcoming and made sure we had a comfortable stay."
Canada
Karunya
$91 nightly
The price is $101
Dec 27 - Dec 28
Total with taxes and fees
Le Mammole

Villa Sestilia

Villa Sestilia
Montaione
9.6 out of 10, Exceptional, (17)
"This is a lovely country property, perfect for relaxing and resting"
United States
Christian
$146 nightly
The price is $164
Jan 11 - Jan 12, 2026
Total with taxes and fees
Villa Sestilia

Il Piastrino

Il Piastrino
Vinci
9.4 out of 10, Exceptional, (42)
"Area"
Canada
Donnabelle
$91 nightly
The price is $104
Dec 27 - Dec 28
Total with taxes and fees
Il Piastrino

Leonardo

Leonardo
Vinci
9.6 out of 10, Exceptional, (15)
"Lovely location just outside town, great pool, good restaurant, good value breakfast, stylish room with great shower, friendly staff. Would stay again "
United Kingdom
stephen
$91 nightly
The price is $101
Dec 27 - Dec 28
Total with taxes and fees
Leonardo

Bellavalle Rooms

Bellavalle Rooms
Vinci
10.0 out of 10, Exceptional, (16)
"The room is really good, quiet, panoramic view...clean, we had a very nice stayng there."
United States
José Marcos
Bellavalle Rooms

Borgo san Benedetto

Borgo san Benedetto
Montaione
9.4 out of 10, Exceptional, (50)
"Lovely grounds, beautiful apartment, grocery stores close by, great jumping off point for exploring Tuscany!"
United States
Suzana
Borgo san Benedetto

Agriturismo Macinatico 1

Agriturismo Macinatico 1
San Gimignano
10.0 out of 10, Exceptional, (9)
"Great family vacation home in a beautiful setting. We stayed for 2 weeks with the family and parents and have a wonderful time. Very friendly and helpful staff, clean property, plenty of amenities."
Belgium
Olivier
Agriturismo Macinatico 1

Tenuta Decimo

Tenuta Decimo
San Gimignano
8.2 out of 10, Very Good, (47)
"The amenities are great- pool, spa, wine tasting. The staff are friendly and were very helpful getting reservations set up."
United States
Lindsay
Tenuta Decimo

Palazzo al Torrione

Palazzo al Torrione
San Gimignano City Centre
8.8 out of 10, Excellent, (56)
"The area of San Gimignano was surprising and beautiful."
United Kingdom
Philip
$126 nightly
The price is $145
Jan 12 - Jan 13, 2026
Total with taxes and fees
Palazzo al Torrione

Colle Alberti Country House

Colle Alberti Country House
Cerreto Guidi
10.0 out of 10, Exceptional, (53)
"Amazing experience all around. Friendly attentive staff, great dining experiences and the perfect atmosphere. "
Canada
Steven
$99 nightly
The price is $112
Jan 6 - Jan 7, 2026
Total with taxes and fees
Colle Alberti Country House

B&B Ponte a Nappo

B&B Ponte a Nappo
San Gimignano
9.4 out of 10, Exceptional, (56)
"Beautiful private property with very comfortable suites with awesome views of San Gimignano and the breathtaking valley. Highly recommend, staff was very accommodating and friendly. "
United States
Mary
$149 nightly
The price is $170
Jan 2 - Jan 3, 2026
Total with taxes and fees
B&B Ponte a Nappo

HOMY BnB

HOMY BnB
Empoli
9.4 out of 10, Exceptional, (14)
"This is just an easy train hop from Florence. Empoli is adorable. If you would like a spot from where you can head out to anywhere in Tuscany, this is a great spot. It has a lovely balcony and Tatiana and other staff where very nice and helpful. "
United Kingdom
Ginger
$119 nightly
The price is $134
Dec 27 - Dec 28
Total with taxes and fees
HOMY BnB
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

What is the best area to stay in Castelfalfi?
The best area to stay in Castelfalfi is within the Borgo, the historic heart of the estate, for a central and authentic Tuscan experience.

The Borgo is the main hub of Castelfalfi, featuring restored medieval buildings, local shops, and restaurants. It's a pedestrian-friendly area centered around the castle and the main piazza. Staying here offers immediate access to the estate's amenities and provides a sense of being part of a small, historic Tuscan village.

Couples will find the Borgo particularly appealing. Its charming streets, intimate dining options, and proximity to vineyards and olive groves create an ideal setting for a romantic getaway. Many accommodations here offer views of the rolling Tuscan hills, superb for enjoying a quiet evening.

Travelers seeking a more secluded and spacious experience might prefer the villas scattered throughout the Castelfalfi estate.
When is the best time to go to Castelfalfi?
The best time to visit Castelfalfi is during the shoulder seasons of late spring (April to early June) and early autumn (September to October).

These periods offer pleasant weather, ideal for exploring the Tuscan countryside without the intense heat of summer or the chill of winter. You'll find comfortable temperatures for outdoor activities like hiking, cycling, or simply enjoying the views from the resort's expansive grounds. The vineyards are either budding with new growth or rich with harvest, providing picturesque scenery.

Couples often find these times great for a romantic getaway. The weather is conducive to leisurely strolls through the olive groves, wine tastings at local vineyards, and enjoying al fresco dining in the evenings. The resort's amenities, including the golf course and spa facilities, are fully operational, offering a relaxed yet refined experience.

For travelers seeking a quiet retreat, these months provide a comfortable balance. The resort is less crowded than during peak summer, allowing for a more serene experience at the pools, restaurants, and other facilities.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Castelfalfi.
How can I save on a Castelfalfi hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Castelfalfi hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Castelfalfi hotel?
Prices for hotels in Castelfalfi often vary, but you can find a great deal from $81 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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