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

Gaiole in Chianti Vacation Rentals

Q: 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 kitchenware. You can relax into your vacation with a garden and a library.

Dates

November 2026

December 2026

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Our top choices for Gaiole in Chianti vacation rentals

A stone building with a yellow sign reading "b&b erioico".

1. L' Eroico

Gaiole in Chianti

Angela

AED 556 total

includes taxes & fees

7 Nov - 8 Nov

A dining area with a table and chairs, a sofa, and large windows with curtains.

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

Gaiole in Chianti

AED 3,492 total

includes taxes & fees

8 Nov - 9 Nov

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

3. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

AED 6,409 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a colorful inflatable ring and a water fountain.

4. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

AED 1,965 total

includes taxes & fees

12 Nov - 13 Nov

A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

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

Gaiole in chianti

AED 1,254 total

includes taxes & fees

22 Nov - 23 Nov

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

Gaiole in chianti

AED 1,324 total

includes taxes & fees

22 Nov - 23 Nov

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

Gaiole in chianti

AED 1,777 total

includes taxes & fees

30 Nov - 1 Dec

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

8. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

AED 473 total

includes taxes & fees

28 Nov - 29 Nov

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

9. Relais Villa Olmo - Place of Charme

Impruneta

Michael

AED 378 total

includes taxes & fees

26 Nov - 27 Nov

A table set with breakfast items on a balcony overlooking a historic town.

10. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

AED 610 total

includes taxes & fees

10 Nov - 11 Nov

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

AED 490 total

includes taxes & fees

9 Nov - 10 Nov

A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

12. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

AED 489 total

includes taxes & fees

8 Nov - 9 Nov

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

13. Terre di Baccio

Greve in Chianti

Gage

AED 1,069 total

includes taxes & fees

15 Nov - 16 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

14. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"Unable to sleep! Do not stay here during the summer. Even though it seemed to cool off at night, and even with a fan, it was so hot in the top bedroom that we sweat all night and did not sleep a wink. Also, there was a dog barking next door so that made it even harder to sleep. For some reason, there isn’t a pool listed in the description but when we complained about the heat, we were told we could use the pool. The property is beautiful but unbearable in terms of getting sleep, I do not...

Michael F.

AED 626 total

includes taxes & fees

9 Nov - 10 Nov

An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

San Casciano in Val di Pesa

Justyna

AED 664 total

includes taxes & fees

23 Nov - 24 Nov

A bakery display with pastries and a coffee station.

16. B&B Il Corso

Siena City Centre

Heather

AED 315 total

includes taxes & fees

30 Nov - 1 Dec

A bathroom with a window view of a historic building and a tiled roof.

17. Siena Vip

Siena City Centre

Jacob

AED 417 total

includes taxes & fees

8 Nov - 9 Nov

A table with two wine glasses, a bottle, and a book.

18. Domus il Palio B&B

Ravacciano

Leo

AED 281 total

includes taxes & fees

18 Nov - 19 Nov

A table with breakfast items and a view of rolling hills.

19. Chianti Village Morrocco

Tavarnelle Val di Pesa

Nirav

AED 300 total

includes taxes & fees

7 Nov - 8 Nov

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

20. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

Stella

AED 487 total

includes taxes & fees

7 Nov - 8 Nov

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Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

L' Eroico

Gaiole in Chianti

10/10 Excellent

Angela

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

The Club House

Castelnuovo Berardenga

10/10 Excellent

debbie

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

Castello La Leccia

Castellina in Chianti

10/10 Excellent

Sarah

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Anonymous traveler

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

La Dimora Dei Monaci

Siena City Centre

10/10 Excellent

we stayed for 4 nights and used Seina as our base for our first visit to Tuscany. The owners were very helpful. They provided maps and information on all the local sights, plus some history of the town. One night we asked them to make dinner reservations and they had to call over 10 places due to a busy night. But they found us a great restaurant for dinner. Another day they provide a detailed schedule for buses to visit one of the towns we were interested in. The B&B is very close to the...

Alan

A motorcycle parked in front of a brick building with arched doorways and a street lamp.

Torre del Fuggisole

Siena City Centre

10/10 Excellent

Charles

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

Tenuta CorteDomina

Radda in Chianti

10/10 Excellent

piyanut

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

Agriturismo San Sano

Gaiole in Chianti

10/10 Excellent

Angela

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

Villa del Sole Siena

Siena City Centre

10/10 Excellent

Linna

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

Relais degli Angeli

Siena City Centre

10/10 Excellent

Stained here at the end of an eight day trip around Italy. This hotel was head and shoulders above the others I visited, it is a boutique hotel of seven rooms. Our room was a suite. It was bigger than many apartments, with a large living room with daybed, a beautiful master bathroom with jetted tub and separate shower with jets overhead as well as side jets, ample closet storage, fridge, and safe. The rooms here have antique furniture and hand painted ceilings. I loved the breakfast on the...

Susie

A brick building with two arched windows, one with a metal grill and the other with a decorative glass design.

Hotel Palazzetto Rosso

Siena City Centre

10/10 Excellent

A Beautiful and Unique Stay in the Heart of Siena! Our stay at Hotel Palazzetto Rosso was an incredible experience! The atmosphere was absolutely amazing, with stunning medieval architecture that perfectly captures the historic charm of Siena. The hotel beautifully blends its centuries-old character with modern comforts, creating a truly unique and memorable experience. The staff was exceptionally friendly and accommodating, especially when it came to our late arrival. They went above and...

Thomas

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

Palazzo di Valli

Siena

10/10 Excellent

We stayed 3 nights at Palazzo di Valli in late April 2022. The property is beautiful and located in a quiet residential area just south of the city's center. It sits on a hill overlooking a valley, and has it's own orchard and flower gardens. Instead of waking up to the sound of motorcycles and delivery trucks under your window, we woke up to chirping birds. Hosts Lorenzo and Giancarlo were wonderful, offering us recommendations, and helping arrange reservations and transportation. It's a bit of...

Joan

A traditional stone building with a garden featuring geometric hedges and potted plants.

Badia a Coltibuono

Gaiole in Chianti

10/10 Excellent

Grace

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Gary

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

COMO Castello Del Nero

Tavarnelle Val di Pesa

10/10 Excellent

Lauren

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

10/10 Excellent

Sarah

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 kitchenware. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 18 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 Terme Antica Querciolaia. 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.

Gaiole in Chianti Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti vacation rentals

1. L' Eroico

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

3. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

4. Farmhouse in Chianti

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

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

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

8. Agriturismo La Ferrozzola

9. Relais Villa Olmo - Place of Charme

10. Residenza d'Epoca Palazzo Borghesi

11. Casa Vacanze Squarcialupi

12. Old medieval apartment

13. Terre di Baccio

14. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

15. Villa il Fedino

16. B&B Il Corso

17. Siena Vip

18. Domus il Palio B&B

19. Chianti Village Morrocco

20. B&B La Fonte del Machiavelli

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

L' Eroico

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Gaiole in Chianti?

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

How many vacation rentals are there in Gaiole in Chianti?

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

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