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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for La Strada-Santa Cristina 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 ฿4,810
฿5,444 total
includes taxes & fees
15 Sept - 16 Sept
San Michele al Borgo

2. 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 ฿2,886
฿3,404 total
includes taxes & fees
11 Oct - 12 Oct
iConic Wellness Resort
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

3. 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 ฿5,232
฿5,908 total
includes taxes & fees
23 Sept - 24 Sept
B&B Piccolo Hotel
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ฿3,422
฿3,917 total
includes taxes & fees
16 Sept - 17 Sept
Vicolo Della Scala Rooms - La Luna
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

5. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ฿4,705
฿5,290 total
includes taxes & fees
17 Sept - 18 Sept
CASA AMBRA
A view of a historic town with prominent buildings and a church tower.

6. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (192 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
The price is ฿2,927
฿3,450 total
includes taxes & fees
22 Sept - 23 Sept
Cameracaffè Centro
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

7. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is ฿10,829
฿12,065 total
includes taxes & fees
19 Sept - 20 Sept
Fontelunga Hotel & Villas
A modern hotel room with large windows, a bed, a desk, and a chair.

8. 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 ฿2,166
฿2,613 total
includes taxes & fees
29 Sept - 30 Sept
B&B 52cento
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

9. 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 ฿2,781
฿3,213 total
includes taxes & fees
14 Sept - 15 Sept
Artisti del Cavallo Tourism
A spa area with a stone-walled arch, a hot tub, and a small window.

10. 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 ฿3,774
฿4,305 total
includes taxes & fees
4 Oct - 5 Oct
DormiVeglia B&B
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

11. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is ฿8,277
฿9,258 total
includes taxes & fees
14 Sept - 15 Sept
Castello di Gargonza
An arched stone bridge with a white building on the right, featuring a balcony with plants.

12. 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 ฿3,938
฿4,332 total
includes taxes & fees
15 Sept - 16 Sept
Locanda Antico Borgo
A stone building with arched windows and a gravel driveway.

13. Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
The price is ฿3,764
฿4,255 total
includes taxes & fees
17 Sept - 18 Sept
Villa La Ginestra
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

14. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ฿3,824
฿4,360 total
includes taxes & fees
15 Sept - 16 Sept
Vicolo Della Scala Rooms - Il Sole

15. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
The price is ฿4,182
฿4,600 total
includes taxes & fees
14 Sept - 15 Sept
Palazzo Tarlati Residenza d'Epoca
A corridor with wooden flooring, a white cushioned bench, and shelves on both sides displaying bottles.

16. Allegra Toscana - Affittacamere Guest house

Allegra Toscana - Affittacamere Guest house
Arezzo Centro Storico
7.0 out of 10, Good, (17 reviews)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
The price is ฿3,204
฿3,908 total
includes taxes & fees
1 Oct - 2 Oct
Allegra Toscana - Affittacamere Guest house
A hotel room with a bed, two bedside tables, a painting on the wall, and a vase with flowers on one of the tables.

17. Room-two-room Apartment

Room-two-room Apartment
Saione
10.0 out of 10, Exceptional, (1 review)
"A little tricky to locate but friendly staff and very walkable to see the sites."
Canada
Thelma
The price is ฿4,025
฿4,658 total
includes taxes & fees
20 Sept - 21 Sept
Room-two-room Apartment

18. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is ฿4,488
฿5,091 total
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
A table set outdoors with a view of mountains, including a basket of pastries, cups of coffee, and a bottle of water.

19. Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6 reviews)
"客室は清潔で、とても可愛いかったです。宿泊場所からの眺望は感動します。 朝食が人生でベスト朝食でした！"
Japan
Tatsuya
The price is ฿4,182
฿4,600 total
includes taxes & fees
14 Sept - 15 Sept
Locanda del Viandante
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

20. Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
The price is ฿8,108
฿8,919 total
includes taxes & fees
1 Oct - 2 Oct
Rustic Holiday Home in Citta di Castello With Swimming Pool
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 La Strada-Santa Cristina Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"
Turia 3-night trip
Posted 12 hours ago
Monastero di Cortona Hotel & Spa

Find out more about La Strada-Santa Cristina

Search for holiday rentals in La Strada-Santa Cristina on Expedia! You can easily find your home rentals, villas, holiday apartments in La Strada-Santa Cristina using one of the methods below:

  • View our selection of featured holiday rentals in La Strada-Santa Cristina
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Look no further and take a look at our great range of rental properties in La Strada-Santa Cristina!

Frequently asked questions

Can I find a holiday rental in La Strada-Santa Cristina?

Yes, there are holiday rentals close to the most popular sights in La Strada-Santa Cristina, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to La Strada-Santa Cristina speak positively about the countryside and wineries in this destination. Make sure you have time to check out the churches and musical theatre during your trip.

What’s there to see and do in La Strada-Santa Cristina?

While exploring the area, visit family-friendly sights like Ravagni Oil Mill, or get outside and enjoy nature at Piazza Guido Monaco. Agricola Buccelletti Winery and Tennis Club Castiglionese are a couple of places you'll find in the wider area.

What’s a holiday rental in La Strada-Santa Cristina like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in La Strada-Santa Cristina. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.