Castellina in Chianti Vacation Home Rentals from CA $142: Search Top Private Vacation Homes for Rent

A stone building with a clock tower, steps leading up to it, and people walking around.

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Our top choices for Castellina in Chianti vacation homes

A stone building with multiple windows and a chimney.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

CA $207 total

includes taxes & fees

Nov 8 - Nov 9

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

2. Casa Marisa in Castellina in Chianti

Castellina in Chianti

CA $431 total

includes taxes & fees

Oct 12 - Oct 13

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

3. The Arch Among the Hills of Castellina

Topina

CA $446 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a bed, a nightstand, a chair, a wardrobe, and a window with curtains.

4. B&B Liveinflorence Centro Storico

Historic Centre of Florence

Rose S.

CA $326 total

includes taxes & fees

Nov 3 - Nov 4

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

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

Casole d'Elsa

"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...

Anonymous traveller

CA $759 total

includes taxes & fees

Oct 12 - Oct 13

A long, narrow hallway with marble flooring and walls, leading to a bright room at the end.

6. Cozy Sweet Marbel room in the center of Florence

Historic Centre of Florence

"We had a wonderful time during our stay. Our host was extremely kind and helpful. Occasionally she would offer us a cup of coffee or cappuccino in the morning and was always responsive to our requests. She was kind enough to let me borrow a wine glass. Very comfortable bed and wonderful room with a small balcony. Would highly recommend especially if you don't mind a shared bathroom with the other guest unit. Would definitely stay again."

Matthew

CA $225 total

includes taxes & fees

Oct 25 - Oct 26

A rustic outdoor seating area with a wicker rocking chair, white plastic chairs, and a table with a teapot.

7. Holiday Home "Le Balze" with Mountain View, Private Garden & Wi-Fi

Castelfranco di Sopra

CA $974 total

includes taxes & fees

Oct 13 - Oct 14

A bedroom with a stone wall, a bed with floral bedding, a view of greenery, and a balcony with metal railings.

8. Holiday Home 'Villa Silvia' with Private Pool, Wi-Fi and Air Conditioning

Rignano sull'Arno

CA $3,212 total

includes taxes & fees

Oct 12 - Oct 13

A spacious living room with a grey sofa, a wooden coffee table, and a chandelier.

9. Lambert Apartment in the Historic Center of Florence

Historic Centre of Florence

Ernesto B.

CA $1,321 total

includes taxes & fees

Oct 15 - Oct 16

A residential area with multiple houses, a swimming pool, and vineyard rows.

10. 'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi

San Gimignano

CA $1,484 total

includes taxes & fees

Oct 17 - Oct 18

An aerial view of a traditional villa with multiple buildings, surrounded by lush greenery and trees.

11. Cosy apartment for 6 people with A/C, pool, WIFI, TV and pets allowed, close to Florence

Impruneta

CA $322 total

includes taxes & fees

Nov 1 - Nov 2

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

12. 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

CA $257 total

includes taxes & fees

Oct 12 - Oct 13

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

13. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

CA $292 total

includes taxes & fees

Oct 12 - Oct 13

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

14. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Toscana

CA $281 total

includes taxes & fees

Oct 18 - Oct 19

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

15. Casa Vacanze Le Case

San Gimignano

Andrew

CA $142 total

includes taxes & fees

Nov 5 - Nov 6

A rustic building with a brick facade, a small arched window, and a door.

16. Cozy Tuscan-style apartment Suitable 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.

CA $295 total

includes taxes & fees

Oct 12 - Oct 13

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

17. Your nest in the Tuscany countryside

Certaldo - Firenze

CA $372 total

includes taxes & fees

Oct 12 - Oct 13

A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

18. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

Siena

CA $280 total

includes taxes & fees

Oct 18 - Oct 19

A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

19. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

Greve in Chianti

Linda L.

CA $584 total

includes taxes & fees

Oct 14 - Oct 15

A swimming pool with a colorful inflatable ring and a water fountain.

20. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

CA $801 total

includes taxes & fees

Oct 12 - Oct 13

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Top Castellina in Chianti Hotel Reviews

Hotel Paris

10/10 Excellent

"Great experience!"

Hotel Horto Convento

8/10 Good

"Beautiful place and room was nice and clean. Breakfast in the morning was nice also (coffee was surprisingly bad). We were booked in their other hotel - Horto Convento. Upon our arrival we were strongly encouraged (coerced?) to move to this hotel - Della Calza. In hind sight, I’m not sure I would have moved - Della Calza is a further walk from the sights of Florence, not as pretty and, while in Florence, we had little interest in the spa."

Villa Neroli

10/10 Excellent

"The room was clean except the walls were dirty and need painting. The flushing mechanism on the toilet needs adjustment. The staff were excellent and friendly. The breakfast bar was excellente. The sea bass on the lunch menu was great. The grounds are well kept and have several outdoor seating so very nice hotel overall."

The Social Hub Florence Lavagnini

10/10 Excellent

"The Social Hub Hotel is very nice and comfortable and is located close to many restaurants, shopping and the train station. Our room was spacious and had a nice large bed and the bathroom was well appointed. The rooftop bar and pool area has an amazing view of the city. The hotel even offers free washers and dryers which was great as I was running out of clean clothes after several weeks of traveling. The staff were very friendly and helpful. I would definitely stay at the Social Hub again."

IQ Hotel Firenze

8/10 Good

"The room was small but manageable. Location was good and walkable if you don’t mind 20 min walks which is a long time if you’re trying to get some where. Staff was extremely helpful. Breakfast had a large variety. Dinner was good. Limited choices though. Loved the cool water in the automatic fountains. Went Sept 8-10. Hotel was a bit pricey for my taste but cute hotel. Had a gym but didn’t use it. The beds were 2 twin size and we pushed them together. We were too tired to ask for a full size or queen. Loved the bidet, the bidet towels and intimate wash. Shower was amazing. The offered some sort of spa service wish we had time to partake. Pros- GYM, spa if you have time, breakfast- many selections even cappuccino, savory and sweet breakfast. Shower nice and spacious!! Bathroom was large. Extremely helpful and kind staff. Water coolers in the hallway to help you stay hydrated. It was very refreshing. Saw microwaves near vending machines in case you had leftovers from dinner. Cons- few selections for dinner, 20-25 min walk from famous sites."

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Number of reviews	95
Accommodation	1926 Vacation Homes
Lowest Price	CA $142
Highest Price	CA $3,212

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti vacation homes

1. Agriturismo La Ferrozzola

2. Casa Marisa in Castellina in Chianti

3. The Arch Among the Hills of Castellina

4. B&B Liveinflorence Centro Storico

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

6. Cozy Sweet Marbel room in the center of Florence

7. Holiday Home "Le Balze" with Mountain View, Private Garden & Wi-Fi

8. Holiday Home 'Villa Silvia' with Private Pool, Wi-Fi and Air Conditioning

9. Lambert Apartment in the Historic Center of Florence

10. 'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi

11. Cosy apartment for 6 people with A/C, pool, WIFI, TV and pets allowed, close to Florence

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

13. Chianti Craft House Badia a Passignano

14. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

15. Casa Vacanze Le Case

16. Cozy Tuscan-style apartment Suitable for families. Pets allowed

17. Your nest in the Tuscany countryside

18. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

19. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

20. Farmhouse in Chianti

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Paris

Hotel Horto Convento

Villa Neroli

The Social Hub Florence Lavagnini

Radisson Blu Hotel, Florence

Hu Firenze Camping In Town

Art Hotel Villa Agape

IQ Hotel Firenze

Plus Florence - Hostel

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Explore a world of travel with Expedia

Castellina in Chianti Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti vacation homes

1. Agriturismo La Ferrozzola

2. Casa Marisa in Castellina in Chianti

3. The Arch Among the Hills of Castellina

4. B&B Liveinflorence Centro Storico

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

6. Cozy Sweet Marbel room in the center of Florence

7. Holiday Home "Le Balze" with Mountain View, Private Garden & Wi-Fi

8. Holiday Home 'Villa Silvia' with Private Pool, Wi-Fi and Air Conditioning

9. Lambert Apartment in the Historic Center of Florence

10. 'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi

11. Cosy apartment for 6 people with A/C, pool, WIFI, TV and pets allowed, close to Florence

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

13. Chianti Craft House Badia a Passignano

14. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

15. Casa Vacanze Le Case

16. Cozy Tuscan-style apartment Suitable for families. Pets allowed

17. Your nest in the Tuscany countryside

18. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

19. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

20. Farmhouse in Chianti

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Paris

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Explore a world of travel with Expedia