Chianti Region Cottages from SAR 430

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Our top choices for Chianti Region cottages

1. Casa il Cipresso, in the heart of Chianti with swimming pool

Castellina in Chianti

2. Casa Antico Roseto - cottage with swimming pool

Castellina in Chianti

"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...

Lisa S.

3. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

Castellina in Chianti

lyndon s.

4. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

Montespertoli

Mark S.

5. Casa Belvedere cottage with swimming pool in the heart of Chianti

Castellina in Chianti

6. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Montespertoli

Studio, Patio, Ground Floor | Terrace/patio

7. Fullino Nero

Siena

Christian

SAR 430 total

includes taxes & fees

4 Aug - 5 Aug

8. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Monteaperti

Ian F.

SAR 810 total

includes taxes & fees

7 Aug - 8 Aug

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Top Chianti Region Hotel Reviews

Relais Vignale & Spa

10/10 Excellent

"This place is absolutely amazing. The pictures don't do it justice. The rooms are simple, but the staff, food, pool, and views are wonderful. I would highly recommend this place as a couples getaway. The included breakfast and nice parking situation were huge benefits as well."

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our hosts and the property lived up to all our expectations! Communication with Beatrice and Jacopo was excellent. This was especially important as we planned this trip ourselves. When we arrived, they were so welcoming. They made us feel at home. This was the perfect Tuscan experience for our family. We were 3 generations and the villa was just what we needed. The pool was a welcome respite after our days out. The kitchen was equipped with everything we needed for the days we chose to cook. But, the best meals of our trip were those cooked by Beatrice and Jacopo! We had breakfast and dinner prepared by them. An abundance of food! Don’t miss out on this! And don’t scroll past this property. Book it and you will be in for a treat!"

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Check prices for these dates

Our top choices for Chianti Region cottages

1. Casa il Cipresso, in the heart of Chianti with swimming pool

2. Casa Antico Roseto - cottage with swimming pool

3. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

4. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

5. Casa Belvedere cottage with swimming pool in the heart of Chianti

6. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

7. Fullino Nero

8. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

9. Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Relais Vignale & Spa

Castello di Spaltenna- Small Luxury Hotels of the World

Villa I Barronci Resort & Spa

Villa San Filippo

Salvadonica - Borgo del Chianti

Villa Il Palagio

Hotel Villa Campomaggio

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Fattoria di Vegi

Search Cottages in Chianti Region

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region cottages

1. Casa il Cipresso, in the heart of Chianti with swimming pool

2. Casa Antico Roseto - cottage with swimming pool

3. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

4. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

5. Casa Belvedere cottage with swimming pool in the heart of Chianti

6. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

7. Fullino Nero

8. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

9. Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Relais Vignale & Spa