A cobblestone square with historic buildings, a fountain, and a church with a bell tower.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Monteriggioni vacation homes

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

1. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is ￥17,397
￥30,928 total
includes taxes & fees
Oct 26 - Oct 27
Siena Love Nest: Romantic Suite with Spa & Jacuzzi
A rustic villa with a garden, a pond, and a mountainous backdrop.

2. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is ￥1,476,093
￥1,476,972 total
includes taxes & fees
Oct 28 - Oct 29
Ebbio – Villa and Organic Farm in Monteriggioni
A stone building with multiple windows and a chimney.

3. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is ￥20,108
￥22,821 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A stone building with a gravel path, outdoor seating, and greenery.

4. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is ￥41,436
￥48,289 total
includes taxes & fees
Nov 1 - Nov 2
The Arch Among the Hills of Castellina
A rustic building with a brick facade, a small arched window, and a door.

5. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

A cozy, Tuscan-style apartment perfect for families. Pets Allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is ￥26,359
￥32,685 total
includes taxes & fees
Oct 26 - Oct 27
A cozy, Tuscan-style apartment perfect for families. Pets Allowed
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

6. House with pool for 4 pax

House with pool for 4 pax
Pievescola
9.4 out of 10, Exceptional, (3 reviews)
"Peaceful, tranquil & quiet retreat with gorgeous but unheated pool - so very refreshing! Lovely, airy & cool rooms. Twin beds were hard but double bed was comfortable. Check side of recycling bin by gate to know what items can be recycled - written instructions were confusing. Hostess Lea delightful & welcoming with hostess Camilla very helpful & warmly wishing us the best!"
Canada
Judith C.
The price is ￥25,041
￥48,939 total
includes taxes & fees
Oct 26 - Oct 27
House with pool for 4 pax
A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

7. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
Casole d'Elsa
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Das Haus ist gut ausgestattet und liegt schön ruhig. Abends kann man das Zirpen der Grillen genießen, den Kauz hören und es kam auch ein Dachs vorbei! Wunderbar für Naturliebhaber. Es ist abseits gelegen. Die Gastgeber sind ausgesprochen nett und haben viele Tipps ! Sehr nette Gastfreundschaft. Ein Ort zum entspannen in der Toscana."
Germany
Anonymous traveler
The price is ￥63,648
￥78,265 total
includes taxes & fees
Nov 2 - Nov 3
Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning
A brick building with a garden, a metal fence, and a clear sky.

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥37,957
￥47,446 total
includes taxes & fees
Nov 1 - Nov 2
Casa Marisa in Castellina in Chianti
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

9. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is ￥42,395
￥46,985 total
includes taxes & fees
Oct 26 - Oct 27
Apartment in Chianti With Pool ID 513
A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

10. Comfortable double room with a bathroom in the historic center of San Gimignano.

Comfortable double room with a bathroom in the historic center of San Gimignano.
San Gimignano City Centre
The price is ￥21,966
￥26,008 total
includes taxes & fees
Oct 26 - Oct 27
Comfortable double room with a bathroom in the historic center of San Gimignano.
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

11. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,190
￥27,897 total
includes taxes & fees
Oct 26 - Oct 27
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

12. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is ￥14,273
￥16,579 total
includes taxes & fees
Nov 2 - Nov 3
Casa Vacanze Le Case
A dining table set with clear glassware and plates, a wooden chair, and a window in the background.

13. IL TOLOMEI - new apartment in the middle of the main street

IL TOLOMEI - new apartment in the middle of the main street
Siena City Centre
8.4 out of 10, Very good, (5 reviews)
"I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer."
United States
Louise B.
IL TOLOMEI - new apartment in the middle of the main street
A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

14. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.
San Gimignano City Centre
The price is ￥23,723
￥35,848 total
includes taxes & fees
Oct 28 - Oct 29
Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.
A balcony with a view of buildings and a vase of flowers.

15. CASA ILARIA - Bright apartment with a view in the historic center

CASA ILARIA - Bright apartment with a view in the historic center
Siena City Centre
8.0 out of 10, Very good, (5 reviews)
"Location was close to restaurants and bars. View from the windows is spectacular. Lots of ups and downs for walking but typical of Italy. Would have liked to see a toaster and handrail on stairs to bedroom, otherwise well equipped. An information booklet including operation of appliances would be helpful."
United States
Phil S.
The price is ￥11,183
￥20,033 total
includes taxes & fees
Oct 27 - Oct 28
CASA ILARIA - Bright apartment with a view in the historic center
A traditional stone building with a tiled roof, surrounded by terraced fields and mountains in the background.

16. A Nest with a View - A Romantic Getaway Within the City Walls

A Nest with a View - A Romantic Getaway Within the City Walls
Radicondoli
The price is ￥27,281
￥27,281 total
includes taxes & fees
Nov 4 - Nov 5
A Nest with a View - A Romantic Getaway Within the City Walls
A rectangular swimming pool with a wooden deck and metal railings, surrounded by a grassy area with trees and a clear sky.

17. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
"Pros: Posto meraviglioso. Bellissima location e bellissimo panorama Cons: Un po' più di cura e pulizia nella zona piscina. Jacuzzi chiusa e pensavamo di trovarla aperta"
Italy
Anonymous traveler
The price is ￥113,167
￥113,870 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

18. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
Tavarnelle Val di Pesa
The price is ￥27,993
￥41,172 total
includes taxes & fees
Nov 2 - Nov 3
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

19. Apartment in Chianti With Pool ID 3939

Apartment in Chianti With Pool ID 3939
Casole d'Elsa
The price is ￥62,475
￥69,074 total
includes taxes & fees
Oct 26 - Oct 27
Apartment in Chianti With Pool ID 3939
A view through a wooden door of a courtyard with stone walls and potted plants.

20. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is ￥21,966
￥31,807 total
includes taxes & fees
Oct 28 - Oct 29
Chianti Craft House Badia a Passignano
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 Monteriggioni Hotel Reviews

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Staff was super helpful and attentive. Beautiful stay"
Elsa 4-night trip
Posted 8 hours ago
Salvadonica - Borgo del Chianti

Find out more about Monteriggioni

Monteriggioni Vacation Homes information

Number of reviews
67
Accommodation
1532 Vacation Homes
Lowest Price
￥16,579
Highest Price
￥1,476,972