Gaiole in Chianti Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Gaiole in Chianti vacation rentals

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

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
$129 nightly
The price is $151
Nov 6 - Nov 7
Total with taxes and fees
L' Eroico
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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
$944 nightly
The price is $949
Nov 9 - Nov 10
Total with taxes and fees
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
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

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
$1,737 nightly
The price is $1,742
Nov 15 - Nov 16
Total with taxes and fees
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A swimming pool with a colorful inflatable ring and a water fountain.

4. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"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."
Germany
Johanna K.
$489 nightly
The price is $534
Nov 13 - Nov 14
Total with taxes and fees
Farmhouse in Chianti
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

Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
$336 nightly
The price is $341
Nov 22 - Nov 23
Total with taxes and fees
Apartment 'Reggioli- Appartamento Falegname' with Mountain View, Shared Garden and Balcony
A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

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

Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
Gaiole in chianti
$355 nightly
The price is $360
Nov 22 - Nov 23
Total with taxes and fees
Apartment 'Reggioli- Appartamento Erborista' with Mountain View, Shared Garden and Wi-Fi
A stone building with a rustic exterior, a gravel driveway, and a dog walking nearby.

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

Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
Gaiole in chianti
$478 nightly
The price is $483
Nov 22 - Nov 23
Total with taxes and fees
Apartment 'Reggioli- Appartamento Del Cestaio' with Mountain View, Shared Garden and Balcony
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

8. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$119 nightly
The price is $136
Nov 9 - Nov 10
Total with taxes and fees
Agriturismo La Ferrozzola
A stone building with a patio area featuring a table and chairs under a large umbrella.

9. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
$91 nightly
The price is $103
Nov 23 - Nov 24
Total with taxes and fees
Relais Villa Olmo - Place of Charme
A table set with breakfast items on a balcony overlooking a historic town.

10. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
$141 nightly
The price is $160
Nov 10 - Nov 11
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
$117 nightly
The price is $131
Nov 9 - Nov 10
Total with taxes and fees
Casa Vacanze Squarcialupi
A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.

12. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (9 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
$128 nightly
The price is $133
Nov 6 - Nov 7
Total with taxes and fees
Old medieval apartment
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

13. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
$260 nightly
The price is $290
Nov 9 - Nov 10
Total with taxes and fees
Terre di Baccio
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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
$163 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
$160 nightly
The price is $180
Nov 23 - Nov 24
Total with taxes and fees
Villa il Fedino
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

16. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
$74 nightly
The price is $86
Nov 12 - Nov 13
Total with taxes and fees
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (496 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
$100 nightly
The price is $115
Nov 9 - Nov 10
Total with taxes and fees
Siena Vip
A table with two wine glasses, a bottle, and a book.

18. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
$66 nightly
The price is $77
Nov 18 - Nov 19
Total with taxes and fees
Domus il Palio B&B
A table with breakfast items and a view of rolling hills.

19. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
$72 nightly
The price is $81
Dec 5 - Dec 6
Total with taxes and fees
Chianti Village Morrocco
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

20. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
$116 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
B&B La Fonte del Machiavelli
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.
View all properties

Find vacation rentals that suit your style

villa image
Villas
Villas
apart-hotel image
Aparthotels
Aparthotels

Top Gaiole in Chianti Hotel Reviews

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

L' Eroico

L' Eroico
Gaiole in Chianti

10/10 Excellent

Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area.
United States
Angela
Reviewed June 15, 2026
L' Eroico

Find out more about Gaiole in Chianti

Everything you need to know about Gaiole in Chianti vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gaiole in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaiole in Chianti vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gaiole in Chianti vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaiole in Chianti. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gaiole in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $82 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gaiole in Chianti rentals

At Expedia, we put the best Gaiole in Chianti vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gaiole in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaiole in Chianti vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaiole in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Explore a world of travel with Expedia