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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 San Chimento holiday rentals

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

1. Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (441 reviews)
"Had an incredible stay here! It was so beautiful and peaceful, the staff was also amazing and super helpful."
Canada
Raman
The price is 3.766.071 ₫
4.349.398 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Hotel Borgo San Luigi
A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

2. Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (229 reviews)
"We couldn’t rate Villa Sabolini more highly - we had such an excellent time. It is a beautiful property and the perfect place to relax and enjoy Tuscany. The staff were so helpful and friendly too."
Australia
Andrew
The price is 3.333.161 ₫
3.784.823 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Villa Sabolini
A stone building with a swimming pool, surrounded by trees and a view of the landscape.

3. Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
9.6 out of 10, Exceptional, (85 reviews)
"Staff were extremely helpful and accommodating. Breakfast and supper are top notch. Location is absolutely beautiful."
Canada
Doug
The price is 4.007.329 ₫
4.555.719 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Relais la Costa - Dimora Storica
A rural pathway flanked by tall trees and purple flowers, leading to a scenic view of the countryside.

4. Relais Castel Bigozzi

Relais Castel Bigozzi
4.0 star property
Monteriggioni
8.8 out of 10, Excellent, (246 reviews)
"beautiful and romantic!"
United States
Paul
The price is 3.852.555 ₫
4.444.530 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Relais Castel Bigozzi
A pathway lined with trees and a large pot in the center.

5. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (142 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is 2.104.231 ₫
2.462.587 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Villa Montarioso
A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.

6. Hotel La Vecchia Cartiera

Hotel La Vecchia Cartiera
3.0 star property
Colle di Val d'Elsa
8.4 out of 10, Very good, (211 reviews)
"The staff was very welcoming. Lovely quiet place. Close to a lot of good restaurants. "
Canada
Sheila
The price is 2.174.593 ₫
2.480.647 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Hotel La Vecchia Cartiera
A courtyard with a statue, stone walls, and a reception sign.

7. Relais Della Rovere

Relais Della Rovere
4.0 star property
Colle di Val d'Elsa
9.0 out of 10, Wonderful, (267 reviews)
"We loved our stay at Relais, all staff were friendly and helpful, especially Jess who helped us with local restaurant ideas and tis for Tuscany. Thanks Jess and the team for a wonderful few days at the perfect base for exploring the region."
Australia
Robert
The price is 3.435.895 ₫
3.897.610 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Relais Della Rovere
An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

8. Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (353 reviews)
"Very nice"
United Kingdom
James
The price is 2.740.469 ₫
3.191.704 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Villa San Lucchese
A person sitting in a hot tub with a waterfall feature in the background.

9. Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA
4.0 star property
Colle di Val d'Elsa
9.4 out of 10, Exceptional, (470 reviews)
"Beautiful place, wonderful pool and great breakfast."
Canada
Maria
The price is 4.349.184 ₫
4.902.228 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Hotel Palazzo San Lorenzo & SPA
A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

10. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (566 reviews)
"Everything about this property is wonderful from the lodging to the staff!"
United States
Leslie
The price is 2.549.012 ₫
3.040.605 ₫ total
includes taxes & fees
19 Oct - 20 Oct
La Certosa di Pontignano
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

11. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (238 reviews)
"Wonderful. Gorgeous Tuscany views, pretty rustic buildings, good restaurant. Everything in good condition. I would definitely stay again."
United States
Rita
The price is 1.583.962 ₫
1.919.547 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Hotel Casafrassi
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

12. Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
9.8 out of 10, Exceptional, (112 reviews)
"Beautiful area"
Australia
Glen
The price is 1.920.837 ₫
2.231.267 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano
An aerial view of a vineyard estate with terraced vineyards, a central building with multiple rooms, and a swimming pool.

13. Hotel Pescille by Double Hospitality

Hotel Pescille by Double Hospitality
3.0 star property
San Gimignano
9.2 out of 10, Wonderful, (371 reviews)
"Great place to eat and rest"
Mexico
Tania
The price is 2.963.003 ₫
3.436.492 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Hotel Pescille by Double Hospitality
A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

14. Hotel Executive

Hotel Executive
4.0 star property
Scacciapensieri
8.4 out of 10, Very good, (551 reviews)
"Nice clean hotel. Breakfast ok. Good parking"
United Kingdom
Susan
The price is 2.641.593 ₫
3.053.557 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Hotel Executive
A person sitting in a corner of a room with tiled walls and a bench.

15. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (363 reviews)
"Good value"
Canada
Frank
The price is 3.428.977 ₫
3.978.981 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Hotel Il Piccolo Castello
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

16. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (203 reviews)
"This hotel is a beautiful romantic getaway. You will relax and take in the lovely Chianti Classico scenery at the pool. At night the restaurant prepared delicious local cuisine and you can pair it with an amazing bottle of local wine!"
United States
Michelle Reene
The price is 3.216.350 ₫
3.715.474 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino
A modern hotel lobby with glass-top tables, a magazine, and a small plant.

17. Best Western Hotel San Marco

Best Western Hotel San Marco
3.0 star property
Siena
9.0 out of 10, Wonderful, (476 reviews)
"The breakfast is quite good."
United Kingdom
C.K.
The price is 2.652.027 ₫
3.065.163 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Best Western Hotel San Marco
A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

18. Sangallo Park Hotel

Sangallo Park Hotel
3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (620 reviews)
"Great hotel extremely helpful staff"
United Kingdom
Linda
The price is 2.929.065 ₫
3.369.904 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Sangallo Park Hotel
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.

19. La Cisterna

La Cisterna
3.0 star property
San Gimignano City Centre
9.2 out of 10, Wonderful, (658 reviews)
"This hotel has the perfect location. The view from our balcony was amazing. Very friendly staff too."
United States
john
The price is 2.679.731 ₫
3.125.223 ₫ total
includes taxes & fees
24 Oct - 25 Oct
La Cisterna
A rock garden with various succulents and plants.

20. Hotel Toscana Ambassador

Hotel Toscana Ambassador
4.0 star property
Poggibonsi
8.0 out of 10, Very good, (368 reviews)
"Room was clean, staff was helpful and easy to park."
United States
Jennifer
The price is 1.830.060 ₫
2.190.585 ₫ total
includes taxes & fees
7 Oct - 8 Oct
Hotel Toscana Ambassador
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 San Chimento Hotel Reviews

Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"We enjoyed our stay. The pool, hotel grounds and location were truly amazing. The food was okay but we enjoyed eating off site more. The farmhouse is very quaint and charming. You can hear others in the farmhouse. It was luxurious in many ways and more basic in other ways. But all together a wonderful stay. I would recommend for sure."
Kathy 5-night trip
Posted 8 hours ago
Poderi Arcangelo

Frequently asked questions

Are there holiday rentals in San Chimento?

Yes, there are holiday rentals close to the most popular sights in San Chimento, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in San Chimento?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Val di Merse. Monteriggioni Castle and Museo del Cristallo di Colle di Val d'Elsa are a couple of places you'll find in the wider area.

What’s a holiday rental in San Chimento like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in San Chimento. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip.