Gaiole in Chianti Holidays

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Top Flight + Hotel Deals in Gaiole in Chianti

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
14 Sept - 17 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The hotel is situated on busy street, it is walking distance from Santa Maria train station, the room was clean but small and the breakfast was average.

Reviewed on 25 Jul 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
14 Sept - 17 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
14 Sept - 17 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (382 reviews)
It is such a beautiful property and our apartment was clean and comfortable. Ate at the lovely restaurant one nigh and had take out the second. The breakfast was fantastic, so delicious with many options. The staff were so friendly and helpful.

Reviewed on 21 Jul 2025

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
per person
30 Sept - 3 Oct
found 9 hours ago
Return direct flight included
Larnaca (LCA) to Florence (FLR)
9.2/10 Wonderful! (956 reviews)
Loved the location and cleanliness, only complaint was the pillows and beds weren't comfortable. (Mattress were hard and pillows too thin)

Reviewed on 16 Jul 2025

Rivalta Hotel

Rivalta Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
14 Sept - 17 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (349 reviews)
Excellent stay in a beautiful property overlooking the river. Staff was wonderful, breakfast was wonderful, room was spacious and beautifully designed. All around excellent!

Reviewed on 22 Jul 2025

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
9.4/10 Exceptional! (237 reviews)
"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during ..."

Reviewed on 16 Jul 2025

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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
9/10 Wonderful! (88 reviews)
"Beautiful property in a stunning location! Would have been nice to have some sort of gathering area indoors as we were multiple pe"

Reviewed on 29 May 2025

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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
8.6/10 Excellent! (129 reviews)
A Relaxing Retreat.
"A quaint and beautifully renovated old mill dating back to the 1400s. The grounds are spacious, and are home to both flowering plants and herbs. Lots of areas to access, both shaded and in full sun. Food was excellent. You are able to access the sister facility, opened recently, just a short distance ..."

Reviewed on 19 Jul 2025

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Ultimo Mulino Wellness Country Hotel
See all 8,784 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.

Popular places to visit

Medieval Tower of Barbischio

Find out about the history of Gaiole in Chianti when you spend time at Medieval Tower of Barbischio. Discover the beautiful countryside in this walkable area or enjoy its local tours.

Medieval Tower of Barbischio

Church of San Sigismondo

You can find out about the history of Gaiole in Chianti with a stop at Church of San Sigismondo. Discover the beautiful countryside and cosy cafes in this quaint area.

Church of San Sigismondo

What to do in Gaiole in Chianti

Brolio Castle

Small-Group Chianti Trip with Wine Tasting from Siena

€180
per adult
Small-Group Chianti Trip with Wine Tasting from Siena
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

€49
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

€86
per adult
Chianti Wineries Tour with 7 Wine Tastings 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 €423 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.

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