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Places to stay in Castellina in Chianti

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Popular amenities for Castellina in Chianti places to stay

Other great vacation rentals in Castellina in Chianti

Guest favorite
A charming stone cottage with a rustic roof is surrounded by lush greenery and colorful plants. The tranquil outdoor area features a pathway leading to the entrance, with a few items like bicycles and a sun umbrella placed nearby.
Guesthouse in Castellina in Chianti
4.86 out of 5 average rating, 192 reviews

Il Giglio Relax in Castellina in Chianti

VanessaRating, 5 stars2 weeks ago
We and our dog felt very comfortable at the place! Stefano was a very warm host. For example, he took us to the supermarket with his car, shared the fruit and vegetables from his garden with us and gave us a great welcome gift with a bottle of wine. Stefano was always available for questions. His two dogs Theo and Rocky were also very sweet. The apartment is on the outskirts, everything is easily accessible on foot. Everything was clean on site, the garden (and especially the pool) were very nice and you had plenty of space and privacy at the same time. 😊
Guest favorite
Apartment in Poggibonsi
4.95 out of 5 average rating, 61 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany, Morellino Apt.

JohnRating, 5 stars1 month ago
We spend here 4 nights with our dog and felt right at home. I love nature and I love to cook and the kitchen being small has everything and a window on the Tuscan landscape, Considering we were not lucky with the weather Antonio gave us a few great tips what to do and we had an amazing time! Also special shoutout to sweet Tilda ❤️ we miss her already John Olya Floyd
Top guest favorite
Apartment in Castellina in Chianti
4.84 out of 5 average rating, 301 reviews

Relax Chianti. Apartment with pool and garden

CédricRating, 5 stars3 weeks ago
Amazing home with stunning views of the Tuscan Chianti landscape. Relaxing calm with the complicity of birdsong. A privilege to share with the family. Our child was very happy to discover his room with new games. Cinzia is a wonderful host. A "high level" home!
Top guest favorite
The exterior of a rustic stone building showcases traditional Tuscan architecture. Decorative wooden lattice windows add character, while flower beds provide a touch of color. The surrounding paved area features seating options, contributing to a welcoming outdoor space.
Apartment in Poggibonsi
4.97 out of 5 average rating, 252 reviews

OLIVE TREE APARTMENT - CHIANTI

AnnaRating, 5 stars1 week ago
What an incredible stay at this beautiful apartment! Pictures don’t do it justice. A true Tuscan paradise. Apartment is spotless. Beautiful touches everywhere and very spacious. The views are incredible. Great front and back porches to relax and take in the beauty. Mario and Nadia are wonderful hosts. Always responsive and a pleasure to interact with. Loved our stay and would definitely come back again. Highly recommend!
Top guest favorite
Apartment in San Gimignano
4.98 out of 5 average rating, 41 reviews

Herons Superior Apartment - Splendid view!

JanineRating, 5 stars3 weeks ago
Words can’t describe how beautiful the view is from the apartment! We had a lovely week in San Gimignano with our six month old. So peaceful and everything within walking distance. Communication was great and use of the parking garage was much appreciated. Would definitely recommend!
Guest favorite
A stone cottage is surrounded by greenery, featuring a paved outdoor area with potted plants. An umbrella shaded table and chairs are visible, providing a space for outdoor dining. The hilltop location offers a serene environment, enhanced by nearby trees.
Apartment in Toscana
4.89 out of 5 average rating, 74 reviews

LECCIO - Apartment in a typical Chianti village

SelçukRating, 5 stars4 weeks ago
Beautiful place to feel Tuscany vibes, peaceful ve have great views. Marco was really responsive host and special thanks to Marco's father because he took care of us for everything. For the location, I would recommend to rent a car even if you didn't use yourself because the house is located in the middle of the countryside of the city and finding taxi is a bit hard in the nearest town(Poggibonsi). We don't drive that's why we didn't rent a car but when we arrived to Poggibonsi, we realized it was risky but we were lucky because we found a local taxi driver and communicated with him for every trip(of course it wasn't cheaper than renting a taxi but worth it). Anyway, highly recommended place. I hope we will come again :)
Top guest favorite
Home in Monteroni d'Arbia
5 out of 5 average rating, 10 reviews

Golden View - Dream farmhouse in Tuscany

JamesRating, 5 stars3 days ago
Perfect peaceful location. In the countryside but close to amenities and 25 minutes to historic Siena with endless restaurants. And in secure gated area. Beautiful views and amenities in the apartment, with sauna and indoor and outdoor hot tubs. A must stay if looking for quiet, peaceful Tuscan experience.
Guest favorite
An aerial view captures a rustic stone building surrounded by lush greenery and tall cypress trees. A sparkling swimming pool is visible in the yard, complemented by sun loungers. Rolling vineyards stretch into the background, enhancing the serene landscape.
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Orgiale Charme Residenz Castle

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

Quick stats about vacation rentals in Castellina in Chianti

  • Total rentals

    60 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    940 reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Frequently Asked Questions

  • How much does it cost to stay in villa rentals in Castellina in Chianti?

    Experience the best of Castellina in Chianti with our villa rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Castellina in Chianti?

    Yes! Work meets play with ease at over 10 vacation rentals in Castellina in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly apartment rentals in Castellina in Chianti?

    Four-legged friends are welcome in Castellina in Chianti. Choose from more than 10 apartment rentals for guests traveling with pets.

  • Do villa rentals in Castellina in Chianti have wifi?

    Absolutely! We offer over 10 villa rentals with wifi in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Are there Castellina in Chianti villa rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 villa rentals with pools in Castellina in Chianti, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Castellina in Chianti?

    Castellina in Chianti has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Castellina in Chianti