Wineries in Chianti Region

Browse for Chianti Region Winery Hotels from $72

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Search over a million flights, hotels, packages, and more

Featured Chianti Region Winery Hotels

Castello Vicchiomaggio
Via Vicchiomaggio, 4, Greve in Chianti, FI
Free CancellationReserve now, pay when you stay
$130
per night
Oct 22 - Oct 23
4.6/5Exceptional! (198 reviews)

"The apartment was amazing. So beautiful, historic and the views are beautiful"…"

Reviewed on Oct 5, 2019

Castello Vicchiomaggio
Castello di Fonterutoli
Via Puccini 4, Castellina in Chianti, SI
Free CancellationReserve now, pay when you stay
$85
per night
Nov 10 - Nov 11
4.6/5Wonderful! (80 reviews)

"We loved the location as it was in a remote village over 1000 years old. The room was very nice and the restaurant was superb."…"

Reviewed on Aug 11, 2019

Castello di Fonterutoli
Il Borgo di Vescine
4 out of 5
Località Vescine, Radda in Chianti, SI
Free CancellationReserve now, pay when you stay
$113
per night
Nov 4 - Nov 5
4.6/5Wonderful! (185 reviews)

"Amazing place, would definitely visit again! The staff were friendly and the food and wine was amazing. The pool was beautiful and very clean. There are amazing views from all areas of the hotel."…"

Reviewed on Jul 15, 2019

Il Borgo di Vescine
Locanda le Piazze
4 out of 5
Localita Le Piazze 41, Castellina in Chianti, SI
Free CancellationReserve now, pay when you stay
$187
per night
Oct 18 - Oct 19
4.8/5Exceptional! (111 reviews)

"Beautiful location, incredibly peaceful and relaxing. Attentive staff but discreet. Exceeded expectations in every way."…"

Reviewed on Oct 1, 2019

Locanda le Piazze
Hotel Villa Campomaggio
4 out of 5
Strada provinciale 2bis, loc. Campomaggio, Radda in Chianti
Free CancellationReserve now, pay when you stay
$98
per night
Oct 29 - Oct 30
4.6/5Wonderful! (78 reviews)

"This property was a DREAM. The room was royal, the pool was incredible, and the grounds are gorgeous. The spa was excellent and we didnt want to leave!"…"

Reviewed on Oct 7, 2019

Hotel Villa Campomaggio
Fattoria San Donato
Localita San Donato 6, San Gimignano, SI
Free CancellationReserve now, pay when you stay
$78
per night
Oct 22 - Oct 23
4.6/5Wonderful! (47 reviews)

"Scenic, peaceful, historical, interesting, great breakfast, lovely hosts."…"

Reviewed on Sep 27, 2019

Fattoria San Donato
Hotel Leon Bianco
3 out of 5
Piazza Della Cisterna 13, San Gimignano, SI
Free CancellationReserve now, pay when you stay
$72
per night
Nov 4 - Nov 5
4.6/5Exceptional! (291 reviews)

"Great location, center of town. Restaurants, shops, sights all within walking distance. Easy drive from Florence, and easy drive to some surrounding towns as well. Staff was very helpful and friendly. I would recommend to anyone traveling to this great little town."…"

Reviewed on Oct 9, 2019

Hotel Leon Bianco
Hotel Casolare Le Terre Rosse
3 out of 5
Loc. San Donato, San Gimignano, SI
Free CancellationReserve now, pay when you stay
$88
per night
Oct 30 - Oct 31
4.4/5Wonderful! (262 reviews)

"Beautiful and nice staff Everything is clean and organized"…"

Reviewed on Sep 24, 2019

Hotel Casolare Le Terre Rosse
Hotel Pescille
3 out of 5
Strada Statale 47, Localita Pescille, San Gimignano, SI
Get Rates
4.5/5Wonderful! (222 reviews)

"- Room had fantastic view/balcony overlooking San Gimignano. - Staff incredibly pleasant, helpful and friendly. - Hotel has a relaxed and chilled vibe."…"

Reviewed on Sep 22, 2019

Hotel Pescille
Villa I Barronci
4 out of 5
Via Sorripa 10, (GPS: Via Empolese), San Casciano in Val di Pesa, FI
Get Rates
4.6/5Wonderful! (198 reviews)

"Lovely hotel and staff were very helpful. Would definitely come back again."…"

Reviewed on Oct 3, 2019

Villa I Barronci
Querceto di Castellina
Località Querceto 9, Castellina in Chianti, Siena
$153
per night
Oct 20 - Oct 21
4.6/5Wonderful! (27 reviews)

"The highlight of my trip!! Beauty vineyard scenic, lovely house with modern facilities, relaxing and peaceful, one night was just too short... Breakfast was good, suggested to join the wine tasting and vineyard tour, also the cooking class if you have time. Tips: No dinner option (except for a group ..."…"

Reviewed on Oct 10, 2019

Querceto di Castellina
Fattoria il Milione
4 out of 5
Via Di Giogoli 12, Florence, FI
Free CancellationReserve now, pay when you stay
Get Rates
3.8/5Good! (57 reviews)

"Beautiful grounds, great to have a washing machine,"…"

Reviewed on Sep 17, 2019

Fattoria il Milione
La Mormoraia
Agriturismo San Gimignano, San Gimignano, SI
Free CancellationReserve now, pay when you stay
$160
per night
Oct 21 - Oct 22
4.7/5Exceptional! (75 reviews)

"This was my favorite experience from going to Tuscany !!! I have to start with the people were honestly amazing!!! They could’ve not been any more nicer!!! The property it is breathtaking!!! The restaurant was definitely five stars gourmet cooking all the way!!!! The staff and the hotel has exceeded ..."…"

Reviewed on Oct 12, 2019

La Mormoraia
il Casale del Cotone
Localita Il Cotone 59 - Cellole, San Gimignano, SI
Free CancellationReserve now, pay when you stay
$90
per night
Oct 30 - Oct 31
4.7/5Exceptional! (112 reviews)

"The property is breathtaking with amazing views of the countryside ."…"

Reviewed on Oct 6, 2019

il Casale del Cotone
Hotel Borgo San Felice
5 out of 5
San Felice, Castelnuovo Berardenga, SI
$356
per night
Oct 21 - Oct 22
4.9/5Exceptional! (45 reviews)

"Amazing place, beautiful, service incredible, food, everything. A hotel I want to be back"…"

Reviewed on Aug 1, 2019

Hotel Borgo San Felice
Farm House La Presura
Via Della Montagnola 191, Strada, Greve in Chianti, FI
Get Rates
4.5/5Wonderful! (24 reviews)
comfortable accommodation in Chianti

"Farmhouse is well located to explore the area, enough restaurants and village supermarkets nearby to cater. Pool was a welcome addition as was effective aircon in room."…"

Reviewed on Sep 16, 2018

Farm House La Presura
La Canonica di Cortine
Località Cortine, 20, Barberino Tavarnelle, FI
Free Cancellation
$109
per night
Oct 20 - Oct 21
4.8/5Exceptional! (25 reviews)
Just Perfect!

"Excellent stay , highly recommended . A lot of options for wine tasting and restaurants in the area, the place is awesome"…"

Reviewed on May 15, 2019

La Canonica di Cortine
Il Vicario
Localita Sant Andrea 1, San Gimignano, SI
$77
per night
Oct 20 - Oct 21
4.7/5Exceptional! (77 reviews)

"The staff were very friendly and the owner cooked and spent lots of time with the guests. A very homelike setting"…"

Reviewed on Oct 3, 2019

Il Vicario
Don't see what you're looking for?
See all available properties in Chianti Region
View all properties
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.

Chianti Region Winery Hotels

If you are looking for a vacation where you spend time enjoying the finer things in life, then look no further than touring a wine region. Chianti Region is quickly becoming a place where wine enthusiast try the latest vintages, as well as those wanting to perfecting their palate. Chianti Region offers the perfect starting point for you to check out all the characteristic of each variety and the qualities that make this town so unique. But even if you are spending most of your afternoons picnicking while admiring vineyards, you'll need a place to stay. Expedia has 2301 hotels near wineries, making it convenient to toast, tour, and take in everything in Chianti Region.

Wine Time All the Time

You're in good hands when you reserve a winery hotel in Chianti Region through Expedia We have everything from luxurious lodgings with pools, spas, and gourmet restaurants to ones that provide just enough to make sure you are relaxed on vacation. And no matter what hotel you choose, rest assured knowing that you will have lots of amenities, a cozy bed, and accommodations near Chianti Region's wineries.

After you get comfortable in your room, begin your grape adventure at some of Chianti Region's best wineries. You'll discover there isn't a more relaxing holiday than learning about new wines and making new friends, all while enjoying the results of so much dedication and hard work. From dark, bold Cabernet Sauvignons to light, crisp Chardonnays, even a trip to one winery can be an adventure unto itself. Sampling local wines while also being surrounded by the very vineyards and the people that produced them is a unique experience that not many getaways can provide.

Reserve a Winery Hotel in Chianti Region Today!

Wine has been the muse for numerous poems, songs, movies, and novels. It makes sense that it could also inspire your next great trip We have hotels near Chianti Region wineries for most budgets. If you are unsure what hotel to choose, then you can scan thorough our review section to see which accommodation is the best fit for you. These deals won't last long. Reserve soon to get the hotel for your Chianti Region vintage vacation.

More trip options

Recently Booked Winery Hotels in Chianti Region

Travelers Loved These Winery Hotels