A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Gaiole in Chianti vacation rentals

Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
$149 nightly
The price is $173
Jul 21 - Jul 22
Total with taxes and fees
L' Eroico
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
$460 nightly
The price is $516
Jul 26 - Jul 27
Total with taxes and fees
Borgo Argenina
Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
$725 nightly
The price is $730
Jul 20 - Jul 21
Total with taxes and fees
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Outdoor dining

'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Gaiole in Chianti
9.6 out of 10, Exceptional, (5 reviews)
"Georgeous clean home in home in an idyllic town! We had a fantastic stay here. I would very happily return."
Germany
Mariah M.
$281 nightly
The price is $286
Jul 27 - Jul 28
Total with taxes and fees
'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
$846 nightly
The price is $851
Jul 24 - Jul 25
Total with taxes and fees
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Gaiole in chianti
$405 nightly
The price is $409
Jul 20 - Jul 21
Total with taxes and fees
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Outdoor dining

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very Good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveler
$1,465 nightly
The price is $1,469
Jul 25 - Jul 26
Total with taxes and fees
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
$446 nightly
The price is $451
Jul 26 - Jul 27
Total with taxes and fees
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Exterior

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
$530 nightly
The price is $535
Aug 1 - Aug 2
Total with taxes and fees
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
$86 nightly
The price is $99
Jul 29 - Jul 30
Total with taxes and fees
Mariani Bed & Breakfast
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (36 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
$171 nightly
The price is $188
Jul 20 - Jul 21
Total with taxes and fees
Villa di Sotto
Outdoor pool

Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very Good, (54 reviews)
"The facilities were great, including access to the swimming pool. The staff were very friendly and helpful. Breakfast options were good. Parking on site. Villa is a 10 minute drive to two lovely Tuscan towns (Greve and Panzano). Would stay here again - it was so atmospheric! "
United Kingdom
Rachel
$125 nightly
The price is $142
Jul 29 - Jul 30
Total with taxes and fees
Villa Rosa Panzano
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Borgo di Erboli

Borgo di Erboli
Cavriglia
$116 nightly
The price is $130
Aug 1 - Aug 2
Total with taxes and fees
Borgo di Erboli
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (71 reviews)
"Beautiful property"
Canada
Mary
$154 nightly
The price is $179
Aug 9 - Aug 10
Total with taxes and fees
Villa Curina Resort
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (325 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
$97 nightly
The price is $110
Jul 21 - Jul 22
Total with taxes and fees
Hu Norcenni Girasole Village
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$149 nightly
The price is $168
Jul 20 - Jul 21
Total with taxes and fees
Residenzia del Sogno
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (53 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$99 nightly
The price is $113
Jul 22 - Jul 23
Total with taxes and fees
Fullino Nero
Apartment, 3 Bedrooms | Living area

Appartamento vicino al Duomo

Appartamento vicino al Duomo
Siena City Centre
10.0 out of 10, Exceptional, (1 review)
"Excellent location. Comfortable beds. Good value for money. Sufficient supplies, plates, pots, pans, etc. Internet worked well."
United States
Sandra
$125 nightly
The price is $142
Jul 29 - Jul 30
Total with taxes and fees
Appartamento vicino al Duomo
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
$67 nightly
The price is $79
Jul 26 - Jul 27
Total with taxes and fees
Domus il Palio B&B
Garden view

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
$94 nightly
The price is $110
Jul 29 - Jul 30
Total with taxes and fees
Villa San Filippo
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 Gaiole in Chianti Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"An absolutely beautiful place to stay. Room was large, bed was very comfortable, view was amazing. Best thing is the garden for a delicious breakfast. Loved staying here. Even the AC worked well, and we were there during the crazy heat.."
Fenny Ann 2-night trip
Posted less than an hour ago
Palazzo Ravizza

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gaiole in Chianti vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gaiole in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gaiole in Chianti rentals

At Expedia, we put the best Gaiole in Chianti vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Gaiole in Chianti?

Yes, we have vacation rentals close to the most popular attractions in Gaiole in Chianti, or you can choose a more secluded option if you're looking for relaxation. The spas and wineries are several reasons why visitors like Gaiole in Chianti. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Gaiole in Chianti has to offer?

Borgo Argiano: Visitors like this Gaiole in Chianti vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 25 Expedia vacation rentals, you're sure to find just the right place for your Gaiole in Chianti stay.

What’s there to see and do in Gaiole in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

What’s a vacation rental in Gaiole in Chianti like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Gaiole in Chianti. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.