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

Gaiole in Chianti Vacation Rentals

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    Check prices for these dates, December 12–13, 2026

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    Our top choices for Gaiole in Chianti vacation rentals

    1. L' Eroico

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

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

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

    3. Farmhouse in Chianti

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

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

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

    5. 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

    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

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

    8. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

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

    9. Agriturismo La Ferrozzola

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

    10. Terre di Baccio

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

    11. Relais Villa Olmo - Place of Charme

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

    12. Casa Vacanze Squarcialupi

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

    13. Chianti Village Morrocco

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

    14. Relais Villa Belpoggio - Residenza d'Epoca

    A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

    15. Villa Cassia di Baccano

    A cozy living room with a stone wall, a wine rack, and two sofas.

    16. Palazzo Pacini

    An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

    17. La Locanda di Pietracupa

    A dining area with a table set for two, featuring a view of greenery through a window.

    18. Siena Vip

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

    19. Tuscasì Aparthotel

    A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

    20. Fullino Nero

    A rustic stone building with a courtyard.

    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.

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    Top Gaiole in Chianti Hotel Reviews

    Hotel Certosa Di Maggiano

    A pool area with a brick building and a tower, surrounded by a well-maintained lawn and distant hills.

    Torre del Fuggisole

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

    La Dimora Dei Monaci

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

    Relais Le Macine di Stigliano

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

    Villa del Sole Siena

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

    Palazzo di Valli

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

    La Veronica Resort

    A poolside area with two lounge chairs and a table, overlooking a hillside with trees and a building.

    Hotel Palazzetto Rosso

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

    Belvedere di San Leonino

    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.

    Borgo Vescine

    A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

    Salvadonica - Borgo del Chianti

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

    Relais Villa Olmo - Place of Charme

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

    Villa il Poggiale - Dimora Storica

    An outdoor dining area with tables and chairs, a striped canopy, and a view of the landscape.

    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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaiole in Chianti vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Gaiole in Chianti vacation rentals we have selected for you start as low as CA $85 per night. Entering your travel dates in the search wizard 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.