A hilltop town with historic buildings, lush green fields, and a clear blue sky.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Sinalunga holiday rentals

Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 4.701.832 ₫
5.261.807 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Abbadia Sicille Relais
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is 8.454.236 ₫
9.419.383 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Fontelunga Hotel & Villas
Interior detail

Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is 2.914.156 ₫
4.223.214 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Castello di Modanella
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is 6.462.298 ₫
7.228.250 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Castello di Gargonza
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is 7.527.829 ₫
8.370.404 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Luxury resort in the Tuscan countryside
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 3.334.546 ₫
3.787.724 ₫ total
includes taxes & fees
31 Jul - 1 Aug
DormiVeglia B&B
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is 4.265.116 ₫
4.811.351 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Meublé Il Riccio
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (38 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is 4.562.246 ₫
5.138.194 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Delcorto Suites
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 2.094.974 ₫
2.454.210 ₫ total
includes taxes & fees
2 Aug - 3 Aug
RESIDENCE LECCIO
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is 3.727.862 ₫
4.220.372 ₫ total
includes taxes & fees
6 Aug - 7 Aug
La Locanda di San Francesco
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is 2.035.652 ₫
2.359.008 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Residenza Fabroni
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (151 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 6.109.443 ₫
6.899.911 ₫ total
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is 2.816.324 ₫
3.217.679 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Bed & Breakfast Vicolo dell'Oste
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.171.332 ₫
2.508.188 ₫ total
includes taxes & fees
5 Aug - 6 Aug
Artisti del Cavallo Tourism
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
United States
Anonymous traveller
The price is 4.949.032 ₫
5.563.808 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Casanova - Panoramic Rooms and Suites
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is 2.473.359 ₫
2.840.418 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Villa Fontis Rapolano
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is 2.700.320 ₫
3.090.143 ₫ total
includes taxes & fees
31 Jul - 1 Aug
PienzaLettings Suites
Front of property

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (31 reviews)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
The price is 2.789.761 ₫
3.188.460 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Podere La Chiusella
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (129 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is 6.308.291 ₫
7.058.843 ₫ total
includes taxes & fees
28 Jul - 29 Jul
Il Tosco
Front of property

montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (6 reviews)
"The views from this property were amazing. The rooms were clean and felt very homey. "
United States
Lori
The price is 3.158.880 ₫
3.594.371 ₫ total
includes taxes & fees
26 Jul - 27 Jul
montorio
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 Sinalunga Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"Agosto and Lucia were so friendly, welcoming and knowledgeable. They give us great advice on what to see, restaurants to visit and where to park. The hotel itself is beautiful. It's clean and has such a European charm. Would definitely stay here again!"
Lorena 1-night trip
Posted 19 hours ago
Hotel Italia

Frequently asked questions

Are there holiday rentals in Sinalunga?

Yes, there are holiday rentals close to the most popular sights in Sinalunga, or you can select a more secluded option if you're looking for a relaxing stay. Sinalunga is known for its wineries and local tours. Make sure you have time to check out the gardens and golf courses during your trip.

How many holiday rentals are there in Sinalunga?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Sinalunga stay.

What’s there to see and do in Sinalunga?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Val di Chiana. In the wider area, you’ll find Golf Club Valdichiana and Valdichiana Outlet Village.

What’s a holiday rental in Sinalunga like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sinalunga. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.