A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Castiglion Fiorentino holiday rentals

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

1. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is 3.664.181 ₫
4.147.428 ₫ total
includes taxes & fees
19 Oct - 20 Oct
San Michele al Borgo
A hotel room with a bed, a chair, a table, and a large window.

2. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is 1.898.908 ₫
2.427.101 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Limehome Arezzo Duomo
Pool

3. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 1.935.739 ₫
2.304.556 ₫ total
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort
Room

4. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
The price is 2.150.763 ₫
2.541.082 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Bibi Boutique
A spa area with a stone-walled arch, a hot tub, and a small window.

5. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.875.585 ₫
3.279.973 ₫ total
includes taxes & fees
12 Oct - 13 Oct
DormiVeglia B&B
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

6. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.118.852 ₫
2.447.566 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Artisti del Cavallo Tourism
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

7. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 3.699.229 ₫
4.127.566 ₫ total
includes taxes & fees
2 Nov - 3 Nov
B&B Piccolo Hotel
A view of a historic town with prominent buildings and a church tower.

8. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (193 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
The price is 2.310.001 ₫
2.716.273 ₫ total
includes taxes & fees
7 Oct - 8 Oct
Cameracaffè Centro
An arched stone bridge with a white building on the right, featuring a balcony with plants.

9. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is 3.000.380 ₫
3.300.418 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Locanda Antico Borgo
A modern hotel room with large windows, a bed, a desk, and a chair.

10. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (81 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is 1.840.372 ₫
2.199.652 ₫ total
includes taxes & fees
18 Oct - 19 Oct
B&B 52cento
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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Top Castiglion Fiorentino Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Beautiful property in the middle of a vineyard! Relaxing."
Kimberly 2-night trip
Posted 1 hour ago
Precise Tale Poggio Alla Sala

Frequently asked questions

Are there holiday rentals in Castiglion Fiorentino?

Yes, there are holiday rentals close to the most popular sights in Castiglion Fiorentino, or you can select a more secluded option if you're looking for a relaxing stay. Castiglion Fiorentino is known for its wineries and churches. Make sure you have time to check out the monuments and art during your trip.

How many holiday rentals are there in Castiglion Fiorentino?

With 85 Expedia holiday rentals, you're guaranteed to find just the right place for your Castiglion Fiorentino stay.

What can I see and do in Castiglion Fiorentino?

Enjoy the area's cultural attractions such as Museo Diocesano, or get outdoors into nature at a spot like Val di Chiana. Tennis Club Castiglionese and Vasari Loggia are other places to visit while you're in town.

What are holiday rentals like in Castiglion Fiorentino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castiglion Fiorentino. Holiday rentals provide amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.