Gaiole in Chianti Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Gaiole in Chianti

Price found within the past 48 hours. Click for updated prices.
Hotel Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
Price was €588, price is now €319 per person
€319
per person
17 Aug - 21 Aug
found 2 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (354 reviews)
clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!

Reviewed on 23 May 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was €890, price is now €412 per person
€412
per person
22 Sept - 25 Sept
found 13 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on 30 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €833, price is now €393 per person
€393
per person
22 Sept - 25 Sept
found 13 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
The property was clean and staff friendly. The only bummer was the reliability of the elevator, mostly just on the day we left, some of our group had to carry their luggage down 4 flights of stairs. But other than that it was a good experience.

Reviewed on 2 Jul 2026

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was €664, price is now €353 per person
€353
per person
17 Aug - 21 Aug
found 2 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (187 reviews)
This was a little slice of heaven and such a hidden gem. This place is by far my favorite that I have been to in Europe

Reviewed on 16 Jun 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was €736, price is now €468 per person
€468
per person
17 Aug - 21 Aug
found 2 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (1,001 reviews)
Great location with great rooms. It was exceedingly hot and the air-conditioning kept up. The roof top bar was amazing- you could see the whole city.

Reviewed on 1 Jul 2026

Top hotels in Gaiole in Chianti

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is €406 per night from 10 Jul to 11 Jul
€406
10 Jul - 11 Jul
includes taxes & fees
9.6/10 Exceptional! (275 reviews)
"It's our favorite place anywhere. This was our second visit. We'll be back next year!"

Reviewed on 29 Jun 2026

Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

Loc. Tornano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is €229 per night from 7 Jul to 8 Jul
€229
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (110 reviews)
"We stayed in Castillo for 5 days and we like it a lot. There was a good combination of medieval castle vibe and modern comfort. Although we’re mostly driving around exploring vineyards and small towns, we enjoyed the Castillo property, swimming pool and beautiful nature."

Reviewed on 13 Jun 2026

Castello di Tornano Wine Resort
Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel

4 out of 5
Localita La Ripresa di Vistareni Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is €187 per night from 8 Jul to 9 Jul
€187
8 Jul - 9 Jul
includes taxes & fees
8.8/10 Excellent! (160 reviews)
"Loved this boutique property. Stayed five nights in the newer section, Le Noci, and would love to go back. The staff were all excellent, friendly and helpful. The pool was stunning. The room was large, comfy, and quiet. Breakfast was delicious and eating on the outside terrace was wonderful as the ..."

Reviewed on 21 Jun 2026

Ultimo Mulino Wellness Country Hotel
See all 8,667 properties in Gaiole in Chianti
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.

Stay near popular Gaiole in Chianti attractions

Castle of Brolio

9.2/10 (44 reviews)
This ancestral seat of the Ricasoli family since 1141 stands as Italy's oldest winery, pivotal in Chianti Classico's development. Stroll through formal gardens before sampling estate wines in historic cellars.
See properties

What to do in Gaiole in Chianti

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

€79
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting

€49
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

€65
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
See all activities in Gaiole in Chianti

Frequently asked questions

How much does a Gaiole in Chianti holiday package cost?
You'll find cheap prices from €319 on Expedia for your Gaiole in Chianti break. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Gaiole in Chianti costs.
What are the cheapest months to go to Gaiole in Chianti?
The off-season is the best time to head to Gaiole in Chianti if you're hoping to keep costs down. Another tip for getting cheap Gaiole in Chianti holiday packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Gaiole in Chianti?
With about 3 days, you'll have plenty of time to visit popular neighbourhoods such as Badia Coltibuono and Vertine during your Gaiole in Chianti holiday. Be sure to also add PoggioBrandani and Castle of Brolio to your must-do list. Up for some more adventures? Consider venturing outside of Gaiole in Chianti on day trips and tours.
Is it worth booking a holiday package to Gaiole in Chianti?
Gaiole in Chianti has everything you need for an amazing getaway — walking trails, cycling and bars and pubs are just the start. Whether you want to check out attractions such as Meleto Castle and Badia a Coltibuono, or take the path less traveled, you'll find plenty to experience on your Gaiole in Chianti holiday.
How to find the best Gaiole in Chianti package deals?
Start your search for a Gaiole in Chianti package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Gaiole in Chianti package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Gaiole in Chianti escape off to a flying start.
Is it cheaper to book a Gaiole in Chianti holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging accommodation and flights separately. Better still, you can customise your Gaiole in Chianti trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Gaiole in Chianti?
If you're considering an impromptu Gaiole in Chianti adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Gaiole in Chianti?

  1. Pick your travel dates: The things you want to do in Gaiole in Chianti and your favourite season can help you decide when to get away.
  2. Budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Gaiole in Chianti.
  3. Decide how long to go away for: Now that you're up to speed on Gaiole in Chianti, you can figure out the right length of your holiday. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Gaiole in Chianti holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.