Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

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


Featured Gaiole in Chianti Winery Hotels

See all 1,656 Hotels in Gaiole in Chianti
Castello di Meleto

Castello di Meleto

Localita Meleto, Gaiole in Chianti
4.8 out of 5 (6 reviews)
Elegant Tuscan getaway - Castle & wine yards Wonderful place to visit - very efficient staff! Better than any hotel stay - resort living at hotel price
  Oct 26, 2014

$101

$101
Cavarchino B&B

Cavarchino B&B

Via di Vertine, 12, Gaiole in Chianti
5.0 out of 5 (2 reviews)
B&B In ParadiseThis place was really amazing! We were personally greeted by our host, Andrea, who really went out of his way to make us feel welcome & highlight things to see & do in the area. He also told us the best places to eat - all of his recommendations were spot on! The B&B is a short walk from the centre ...
  Jul 17, 2017

$141

$141
Castellare De' Noveschi

Castellare De' Noveschi

Via Padre Chiantini, 12, Gaiole in Chianti
4.8 out of 5 (8 reviews)
Beautiful, Quaint Hotel Staying here we felt like one of the locals. Our room was clean, beautiful, and the window gave us a view of the rolling hills. The hotel owners were incredibly friendly, offering a glass of wine upon arrival. We cannot speak highly enough of their hospitality! Our favorite hotel during our trip ...
  Jun 30, 2017
Il Colombaio di Cencio

Il Colombaio di Cencio

Località Cornia, Gaiole in Chianti
5.0 out of 5 (1 reviews)
Borgo Casa al Vento

Borgo Casa al Vento

Località Casa Al Vento - Barbischio, Gaiole in Chianti
4.3 out of 5 (3 reviews)
DON'T MISS THE WINESWHAT A FANTASTIC GETAWAY FROM THE REAL WORLD. NESTLED ON A WORKING VINEYARD HIGH IN SIENNA. GREAT SAN GERVASE GRAPES "A RIA WINE CLASSICO"
  May 27, 2017

$149

$149
Rocca di Castagnoli

Rocca di Castagnoli

Localita di Castagnoli, Gaiole in Chianti
4.6 out of 5 (5 reviews)
Beautiful serene setting in a castle in TuscanyThe setting was serene and rustic, the views breathtaking, staff was gracious and the dinner was exquisite. I want to live there!
  Oct 14, 2017
Agriturismo Il Crocino

Agriturismo Il Crocino

via di Bellaria, 5, Gaiole in Chianti
Badia a Coltibuono

Badia a Coltibuono

Località Badia a Coltibuono, Gaiole in Chianti
5.0 out of 5 (1 reviews)
Beauty and calm from another timeI loved this B&B! It was so peaceful and calm. It felt like it was from another time. The gardens were gorgeous, and the property is surrounded by forests with trails. Amenities such as a computer room with internet allowed us to have our creature comforts and stay connected.
  Oct 1, 2012

$121

$121
Castello di Spaltenna

Castello di Spaltenna

Via Spaltenna 13, Gaiole in Chianti
5.0 out of 5.0
4.7 out of 5 (36 reviews)
Amazing hotel with an amazing view! Came here for our honeymoon, great staff, amazing restaurant, clean rooms, great landscaping, beautiful facilities
  Oct 4, 2017

$214

$214
Castello di Tornano

Castello di Tornano

Loc. Tornano, Gaiole in Chianti
4.5 out of 5 (4 reviews)
Castle GetawayAn amazing place! We found peace and quiet, it was the perfect place to regroup after the hustle and bustle of Rome and Venice. We stayed in one of the 2 bedroom apartments, and it was the perfect size for our family of four. Our two boys loved the idea of staying at a castle with a pool and my husband ...
  Jun 25, 2012

$121

$121
L'Ultimo Mulino

L'Ultimo Mulino

Localita La Ripresa di Vistareni, Gaiole In Chianti
4.0 out of 5.0
4.2 out of 5 (36 reviews)
Staff was outstanding We were welcomed with a drink and friendly conversation- the hotel is beautiful- the rooms are very clean - the surroundings are Tuscany at its very best- highly recommended
  May 30, 2017

$115

$115
Le Noci

Le Noci

Podere Le Noci 1, Gaiole in Chianti
3.0 out of 5.0
3.5 out of 5 (6 reviews)
La Fonte del Cieco

La Fonte del Cieco

Via Ricasoli 18, Gaiole in Chianti
3.0 out of 5.0
3.8 out of 5 (4 reviews)
Nice place in a dead town.Having never been to the Chianti region before, I didn't realize that Griole in Chianti was a bit removed from the vineyards. The La Fonda was in the town square, which sounds lovely, and maybe sometimes is, but when we were there (May), it was dead. Plus it was exhausting to lug our luggage from ...
  Jun 20, 2013

$66

$66
Castello Vertine

Castello Vertine

Loc. Vertine, 15, Gaiole in Chianti
4.0 out of 5 (4 reviews)
This is a 1,000 years old castle carefully kept Yes, one thousand years old bulding upgrades to all the necessary amenities. The view of the Tuscany hills from all windows are spectacular. Both the interior and the grounds, including the swimming pool are perfectly well kept. THis was a rewarding experience.
  Sep 12, 2016
Hotel Residence San Sano

Hotel Residence San Sano

Località San Sano, Gaiole in Chianti
3.0 out of 5.0
4.2 out of 5 (4 reviews)
Spacious comfortable rooms. Beautiful medieval style hotel.
  Oct 23, 2016

$127

$127
Hotel Le Pozze Di Lecchi

Hotel Le Pozze Di Lecchi

Loc. Molinaccio, Gaiole in Chianti
4.0 out of 5.0
4.3 out of 5 (3 reviews)
Difficult access by bike but gorgeous oasis. Beatiful architecture, landscaping, pool, excellent breakfast buffet and comfortable rooms. Clean modern bathrooms. Highly recommend this hotel as an off-the--beaten track beauty.
  Sep 29, 2017

$115

$115
Casa Vacanze San Regolo

Casa Vacanze San Regolo

Località San Regolo, Gaiole in Chianti
La Pieve Marsina

La Pieve Marsina

Loc. Argenina, Monti in Chianti, Gaiole in Chianti

$176

$176
Castellare in Chianti

Castellare in Chianti

Strada Provinciale 73/B Km 7,2, Gaiole in Chianti
Map

Gaiole in Chianti Winery Hotels Information

Sip on the regions finest wines at a vineyard hotel in Gaiole in Chianti.
  • Browse our wide selection of 1656 winery hotels
  • Receive the lowest rates around on accommodations
  • Book today and sample vinos tomorrow

Before the wine goes to your head, book an accommodation here on Expedia for the cheapest rates on the market.

Then once you have reservations at a winery hotel, you can sip on all the wine you want, because you'll be near all the grape-tasting action. After all, Gaiole in Chianti winery hotels put you in the perfect spot to sample the region's best vintages. Staying within close proximity to a winery is something every Pinot-loving tourist should experience at least once; the views are spectacular and the scenery is serene.

At these inviting winery hotels in Gaiole in Chianti, indulge in nightly tasting events, sample innovative cheese pairings, and learn more about how each vineyard makes its versions of the celebrated drink. Some vineyards in Gaiole in Chianti even let vino enthusiasts tour the wine cellars, meet the region's top sommeliers, and sip a selection of the newest varietals. From grape stomping adventures to palate opening tips, a wine vacation makes for a one-of-a-kind sojourn.

Whether you're a wine tasting beginner or a true aficionado who knows everything about bouquets, notes, and finishes, our 1656 vineyard hotels are sure to offer a little something special for you. Check out our vast selection of wine country accommodations to find one suiting both your tastes and price range. When you make your reservations today, you just may find you have cash leftover to splurge on a case of your favorite Pinot Noir.