Monteriggioni Holiday Houses

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

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Our top choices for Monteriggioni holiday 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

Toscana

includes taxes & fees

2 Nov - 3 Nov

A rustic villa with a garden, a pond, and a mountainous backdrop.

2. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

includes taxes & fees

1 Nov - 2 Nov

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

3. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

includes taxes & fees

8 Nov - 9 Nov

A stone building with a gravel path, outdoor seating, and greenery.

4. The Arch Among the Hills of Castellina

Topina

includes taxes & fees

2 Nov - 3 Nov

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

Toscana

"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."

Shanti R.

includes taxes & fees

31 Oct - 1 Nov

A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

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

Casole d'Elsa

Anonymous traveller

includes taxes & fees

2 Nov - 3 Nov

A brick building with a garden, a metal fence, and a clear sky.

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

includes taxes & fees

1 Nov - 2 Nov

A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

8. Apartment in Chianti With Pool ID 513

Casole d'Elsa

includes taxes & fees

12 Nov - 13 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

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

Ruffoli

"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...

James

includes taxes & fees

3 Nov - 4 Nov

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

10. Casa Vacanze Le Case

San Gimignano

Andrew

includes taxes & fees

3 Nov - 4 Nov

A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

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

San Gimignano City Centre

includes taxes & fees

1 Nov - 2 Nov

A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

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

San Gimignano City Centre

includes taxes & fees

2 Nov - 3 Nov

A stone building with a sign reading "VIA DI CALZOLERIA".

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

Siena City Centre

Louise B.

includes taxes & fees

2 Nov - 3 Nov

A balcony with a view of a stone building and surrounding landscape.

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

Radicondoli

includes taxes & fees

1 Nov - 2 Nov

A view through a wooden door of a courtyard with stone walls and potted plants.

15. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

includes taxes & fees

1 Nov - 2 Nov

An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

16. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Monteroni d'Arbia

includes taxes & fees

5 Nov - 6 Nov

A room with a large window, a view of a balcony with outdoor furniture, and a kitchen area with a sink.

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

Siena City Centre

Phil S.

includes taxes & fees

5 Nov - 6 Nov

18. Apartment in Chianti With Pool ID 3939

Casole d'Elsa

includes taxes & fees

12 Nov - 13 Nov

A rectangular swimming pool with a wooden deck and metal railings, surrounded by a grassy area with trees and a clear sky.

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

Castelnuovo Berardenga

Anonymous traveller

includes taxes & fees

2 Nov - 3 Nov

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

20. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

includes taxes & fees

15 Nov - 16 Nov

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Top Monteriggioni Hotel Reviews

Hotel Athena

8/10 Good

"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"

Castelfalfi

10/10 Excellent

"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay was ultra responsive, during our stay they were always present. You want attention to detail, Castelfalfi has it covered. Drinks are carefully made and delivered. Turn down service straightened the room, put little clothes under anything we had on the bathroom sink or room table, a new bookmark was left next to my book on the nightstand, cords were always wrapped and made to look tidy, I could go on and on. The food in the various restaurants was amazing. The little meat and cheese shop made a tremendous& fresh sandwich sliced up right in front of us on fresh baked bread. The view of sunset from the back deck had many guests out watching for good reason. The spa pool was great and the gym was pretty big. The breakfast buffet had everything you could want. Want fresh honey? There was a station with a honeycomb taken from their property…it drips fresh honey into a tray that empties into a bowl for you. The wine tasting was fun and delicious and worth it. Everything is on site and you will not want to leave the property during your stay or at the end of your trip. Castelfalfi- I hope and pray I return some day, thank you!!"

Il Chiostro del Carmine

10/10 Excellent

"Everything about this place is excellent. We had a wonderful stay and beautiful views of the sunrise! One thing to note is that you do have to take a flight of stairs to your room as there is no elevator. If you have luggage you may want to take this into consideration. We did and it was manageable!"

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

Find out more about Monteriggioni

Monteriggioni Holiday Homes information

Number of reviews	66
Accommodation	1382 Holiday Homes
Lowest Price	NZ$180
Highest Price	NZ$16,708

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monteriggioni holiday homes

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

2. Ebbio – Villa and Organic Farm in Monteriggioni

3. Agriturismo La Ferrozzola

4. The Arch Among the Hills of Castellina

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

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

7. Casa Marisa in Castellina in Chianti

8. Apartment in Chianti With Pool ID 513

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

10. Casa Vacanze Le Case

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

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

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

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

15. Chianti Craft House Badia a Passignano

16. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

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

18. Apartment in Chianti With Pool ID 3939

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

20. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Find holiday rentals that suit your style

Top Monteriggioni Hotel Reviews

Hotel Athena

Grand Hotel Continental Siena – Starhotels Collezione

Castelfalfi

Palazzo Ravizza

Il Chiostro del Carmine

Hotel Minerva

Hotel Borgo San Luigi

Salvadonica - Borgo del Chianti

Hotel Chiusarelli

Find out more about Monteriggioni

Monteriggioni Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Monteriggioni

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monteriggioni holiday homes

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

2. Ebbio – Villa and Organic Farm in Monteriggioni

3. Agriturismo La Ferrozzola

4. The Arch Among the Hills of Castellina

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

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

7. Casa Marisa in Castellina in Chianti

8. Apartment in Chianti With Pool ID 513

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

10. Casa Vacanze Le Case

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

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

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

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

15. Chianti Craft House Badia a Passignano

16. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

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

18. Apartment in Chianti With Pool ID 3939

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

20. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Find holiday rentals that suit your style

Top Monteriggioni Hotel Reviews

Hotel Athena

Find out more about Monteriggioni

Monteriggioni Holiday Homes information

Explore a world of travel with Expedia