Gaiole in Chianti Hotels from S$89

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Our top choices for Gaiole in Chianti hotels

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (91)
Immerse yourself in authentic Tuscany at this historic castle estate. Enjoy wine tastings at the on-site winery, cool off in the seasonal outdoor pool, and dine at La Fornace di Meleto restaurant. Free WiFi and parking complement the beautiful garden and terrace settings.

"This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying."
United States
Karem
Castello di Meleto

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
Set in Gaiole in Chianti with views of the Tuscan countryside, this affittacamere offers daily buffet breakfast and tranquil garden spaces. Explore nearby Medieval Tower of Barbischio or unwind on the scenic terrace after a day of wine tasting.

"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
8.6 out of 10, Excellent, (38)
Escape to this Chianti countryside farm stay featuring 2 outdoor pools and a rooftop terrace. Indulge in local cuisine at the restaurant after exploring the on-site winery. Cantalici Winery and Medieval Tower of Barbischio await nearby.

"Cute secluded property l!"
United States
Courtney
The price is S$279
includes taxes & fees
7 Jan - 8 Jan, 2026
Borgo Casa al Vento

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
Escape to this Gaiole in Chianti affittacamere with an outdoor pool and attached winery. Savour meals at the restaurant before relaxing on the rooftop terrace with garden views. Cantalici Winery and Medieval Tower of Barbischio await nearby.

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is S$253
includes taxes & fees
4 Jan - 5 Jan, 2026
Rocca di Castagnoli

Agriturismo Crocino in Chianti

Agriturismo Crocino in Chianti
Gaiole in Chianti
9.0 out of 10, Wonderful, (2)
Sip local vintages at this farm stay's attached winery in Gaiole in Chianti. Cool off in the outdoor pool or relax in the hot tub after exploring nearby Meleto Castle. Free WiFi and parking complete the authentic Tuscan countryside experience.

"Eines der herzlichsten Hotels, welches wir auf unserer Reise besucht haben."
Switzerland
Cornelia
The price is S$216
includes taxes & fees
31 Jan - 1 Feb, 2026
Agriturismo Crocino in Chianti

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1614)
Dive into the seasonal outdoor pool or the dedicated children's pool at this well-located Florence retreat. Just a 10-minute drive from Uffizi Gallery and Ponte Vecchio, guests love the helpful staff, restaurant, and 3 poolside bars. Florence Rovezzano Station is only a 10-minute walk away.

"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1004)
This business-friendly hotel offers a scenic rooftop terrace, free WiFi, and complimentary parking. Guests praise the delicious breakfast and attentive staff. Sample local cuisine at Mangia restaurant, relax at the bar, or visit nearby National Museum of Archaeology.

"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is S$121
includes taxes & fees
27 Jan - 28 Jan, 2026
Hotel Athena

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1000)
Charming hotel with a restaurant and garden terrace near Stadio Artemio Franchi. Enjoy the complimentary breakfast before exploring nearby Fontebranda. The attentive staff ensures a comfortable stay while room service and free WiFi add convenience.

"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
United States
Kenneth
The price is S$134
includes taxes & fees
9 Jan - 10 Jan, 2026
Hotel Chiusarelli

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (480)
Experience Tuscan charm at this hillside hotel with outdoor pool and poolside bar. Enjoy local cuisine at Ristorante Cortefreda after a day of massages at the spa. Near Abbey of Passignano and Casa Sola Winery with helpful staff to enhance your stay.

"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is S$124
includes taxes & fees
6 Jan - 7 Jan, 2026
Hotel Borgo di Cortefreda Relais

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.2 out of 10, Very good, (51)
Set in a convenient location near historic attractions, this hotel offers a restaurant and bar/lounge where guests can relax. Free WiFi and parking enhance the stay, while Basilica di Santa Maria dei Servi is easily accessible.

"Nice place to stay. Fairly close to the medieval area. No need to worry about any ZTL issue. "
United States
joseph
Palace Hotel Due Ponti

JOIVY Together Florence Secret Nest

JOIVY Together Florence Secret Nest
3.0 star property
Oltrarno
9.2 out of 10, Wonderful, (474)
Enjoy a peaceful stay at this family-friendly hotel within a quick drive to Florence's iconic spots like Piazza della Signoria and Piazzale Michelangelo. Unwind at the bar after exploring Uffizi Gallery, then wake up to a free breakfast served daily.

"Is very nice place to stay, nice staff to comunícate. Very close to transportation and to local shops and restaurant"
United States
Belkys
The price is S$135
includes taxes & fees
7 Jan - 8 Jan, 2026
JOIVY Together Florence Secret Nest

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence
4.0 star property
Florence
8.0 out of 10, Very good, (3)
Situated within a 10-minute drive of Uffizi Gallery and Ponte Vecchio, this hotel offers an inviting outdoor pool. Enjoy local cuisine at La Primavera restaurant, a relaxing bar, and fitness centre. Convenient to Piazzale Michelangelo and Florence Rovezzano Station.

"Great place I love it"
United States
Christian
The price is S$180
includes taxes & fees
18 Jan - 19 Jan, 2026
Radisson Blu Hotel, Florence

Villa Castiglione

Villa Castiglione
2.0 star property
Impruneta
8.6 out of 10, Excellent, (256)
Escape to this family-friendly hotel featuring an outdoor pool, children's splash area, and poolside bar. Just 15 minutes from Florence attractions like Pitti Palace and Ponte Vecchio, with free breakfast, WiFi, and parking.

"Nice and cute place. Great price. "
United States
Jozsef
The price is S$89
includes taxes & fees
11 Jan - 12 Jan, 2026
Villa Castiglione

L'Una Dimora

L'Una Dimora
Certaldo
The price is S$134
includes taxes & fees
3 Jan - 4 Jan, 2026
L'Una Dimora

Hotel Italia

Hotel Italia
3.0 star property
Camollia
9.2 out of 10, Wonderful, (1001)
Experience Siena from this convenient hotel near the train station. Enjoy hiking and mountain biking trails nearby, plus visit Porta Camollia and Siena Stadium. Relax at the bar or on the terrace after exploring. Guests consistently praise the helpful staff and morning breakfast.

"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is S$98
includes taxes & fees
14 Jan - 15 Jan, 2026
Hotel Italia

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (33)
Immersed in wine country near Monteriggioni Castle, this charming hotel offers traditional regional cuisine and comfortable accommodation. Enjoy free breakfast, WiFi, and parking while exploring nearby Lilliano Estate Winery.

"Very nice staff and very nice place to stay."
United Kingdom
Ryan
The price is S$153
includes taxes & fees
18 Jan - 19 Jan, 2026
Hotel Ristorante La Dama nella Vigna

Sangallo Park Hotel

Sangallo Park Hotel
3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (595)
Seasonal outdoor pool and bar create an inviting atmosphere at this Siena hotel. Just an 18-minute walk from the station with easy access to Casalvento's Wines and Palasport Mens Sana. Free breakfast, WiFi, and parking enhance your stay.

"Spacious accommodation and everything works! Great parking, pool and gardens with views across the valley to nearby Siena. Very nice breakfast and lovely staff. Excellent value too!"
United Kingdom
David
The price is S$131
includes taxes & fees
6 Jan - 7 Jan, 2026
Sangallo Park Hotel

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (423)
Set adjacent to a golf course with easy access to Fontebranda and Piccolomini Library. This hotel offers refrigerators and microwaves in rooms, plus free WiFi and room service. Guests love the helpful staff and clean accommodation.

"A great location!"
Canada
Cheryl
The price is S$205
includes taxes & fees
4 Jan - 5 Jan, 2026
Siena Vip

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
Soak in Tuscany from the rooftop terrace at this charming Castelnuovo Berardenga retreat. The on-site restaurant serves Italian cuisine throughout the day, while the garden setting creates a peaceful atmosphere. Terra di Seta and free perks like WiFi, parking, and breakfast add value.

"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is S$168
includes taxes & fees
5 Jan - 6 Jan, 2026
La Certosa di Pontignano

Villa Olmi Firenze

Villa Olmi Firenze
4.0 star property
Bagno a Ripoli
9.4 out of 10, Exceptional, (757)
Unwind at this Bagno a Ripoli retreat with a refreshing outdoor pool and garden. Just 10 minutes from Uffizi Gallery and Piazza della Signoria, enjoy the fitness centre, have drinks at the bar, or grab snacks at the deli. Staff receive top marks from guests.

"Amazing rooms and the breakfast buffet is unbelievable so many choices you won't be disappointed."
United States
michelle
The price is S$155
includes taxes & fees
4 Jan - 5 Jan, 2026
Villa Olmi Firenze
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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Stay near popular Gaiole in Chianti attractions

Learn more about Gaiole in Chianti

Medieval stone buildings house family-run wine shops where you can taste Chianti Classico from surrounding vineyards. Join locals at Piazza Ricasoli's cafés before exploring L'Eroica cycling route that winds through nearby hilltop villages.

View over the hills from the Brolio Castle

Top Gaiole in Chianti Hotel Reviews

More cheap stays in Gaiole in Chianti

Frequently asked questions

Where is the best place to stay in Gaiole in Chianti?
Based on our traveller data, Castello di Spaltenna- Small Luxury Hotels of the World is one of the top choices for your stay. This hotel offers a full-service spa and 2 restaurants. Ultimo Mulino Wellness Country Hotel is another good option for your trip. See all available top hotels, or vacation rentals in Gaiole in Chianti.
What are some of the best holiday rentals that Gaiole in Chianti has to offer?
Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library. See all vacation rentals in Gaiole in Chianti.
If I need to cancel my hotel reservation in Gaiole in Chianti, will I receive a refund?
Yes! Most hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Gaiole in Chianti.
What's the best family accommodation in Gaiole in Chianti?
Ultimo Mulino Wellness Country Hotel is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Other good choices for your stay with the children include Agriturismo San Sano and Hotel Le Pozze Di Lecchi. Also, attractions in the area such as Borgo di Vescine - Tenute di Castelvecchi and Siena Circuit are fun for children of all ages. Find more child-friendly accommodations in Gaiole in Chianti.
What is the favourite LGBTQ-friendly hotel in Gaiole in Chianti?
Castello di Tornano Wine Resort is one of the top choices for those in the LGBT community. Agriturismo Crocino in Chianti is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Gaiole in Chianti.
What's the best dog-friendly place to stay in Gaiole in Chianti?
Ultimo Mulino Wellness Country Hotel is a top hotel for people travelling with their pets, and offers a full-service spa and a restaurant for its human guests. Other good choices for you and your pet include Castello di Tornano Wine Resort and Borgo Le Noci Chianti Retreat & Pool. See more pet-friendly hotel accommodations in Gaiole in Chianti.
What are some accommodation options with pools in Gaiole in Chianti?
Ultimo Mulino Wellness Country Hotel is a top hotel with an outdoor pool, a full-service spa and free buffet breakfast. View all hotels with pools in Gaiole in Chianti.
What is the best spa hotel in Gaiole in Chianti?
Castello di Spaltenna- Small Luxury Hotels of the World is a top spa hotel featuring a vineyard, a fitness centre, tennis courts and a bar. Treat yourself to a facial, body scrub or deep-tissue massage at La Pieve. Other popular spa hotels in Gaiole in Chianti include Ultimo Mulino Wellness Country Hotel and Borgo Le Noci Chianti Retreat & Pool. See all spa hotels in Gaiole in Chianti.
What's it like staying in Gaiole in Chianti?
Visitors to Gaiole in Chianti will definitely enjoy the spas and wineries. Tourists can also enjoy so much more including its monuments. In Gaiole in Chianti, there are 286 hotels and other accommodation options to choose from. Find out more about Gaiole in Chianti.
What should I see while I'm in Gaiole in Chianti?
Landmarks like Meleto Castle, Badia a Coltibuono and Castle of Brolio might be worth a visit. Wine tasting is a great activity, and Cantalici Winery is one place to visit. A couple of additional sights to add to your itinerary are Gaiole in Chianti Stadium and Medieval Tower of Barbischio. Take a look at what more there is to see and do in Expedia's Gaiole in Chianti guide.
What's the seasonal weather in Gaiole in Chianti?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Gaiole in Chianti is 935 mm.

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