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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Sinalunga holiday rentals

A historic building with a tower, a courtyard, and a well-lit entrance.

1. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
"Great Historical location."
Canada
Robert
The price is 2.468.667 ₫
2.802.570 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Abbadia Sicille Relais
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

2. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.098.792 ₫
2.424.394 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Artisti del Cavallo Tourism
An arched stone gateway leading to a pathway lined with potted plants and lights.

3. 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 2.587.300 ₫
3.832.500 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Castello di Modanella
A building with a sign for 'Residence Leccio' and a café named 'La Rumba Café'.

4. RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.4 out of 10, Exceptional, (8 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is 2.130.353 ₫
2.488.042 ₫ total
includes taxes & fees
21 Oct - 22 Oct
RESIDENCE LECCIO
A spa area with a stone-walled arch, a hot tub, and a small window.

5. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.856.375 ₫
3.258.060 ₫ total
includes taxes & fees
8 Nov - 9 Nov
DormiVeglia B&B
A patio area with outdoor seating, potted plants, and a view of the landscape.

6. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (73 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is 2.804.965 ₫
3.805.836 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Affitacamere Maria Gabriella
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

7. 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 2.390.730 ₫
2.745.526 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Villa Fontis Rapolano
A tray with a teapot, two cups of tea, a plate with pastries, and a plate with cookies.

8. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 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 2.046.581 ₫
2.367.287 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Residenza Fabroni
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

9. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (163 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is 3.340.342 ₫
3.848.076 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

10. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is 7.292.555 ₫
8.137.533 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Fontelunga Hotel & Villas
Front of property

11. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful place, view and city."
United States
Federico
The price is 2.911.588 ₫
3.318.354 ₫ total
includes taxes & fees
20 Oct - 21 Oct
montorio
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

12. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 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 2.729.894 ₫
3.118.932 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A stone building with a sloped roof, a small porch, and a gravel driveway.

13. Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.2 out of 10, Wonderful, (33 reviews)
"We enjoyed our stay. Everything was clean and comfortable, and the complex itself was impressive and a stunning place to stay. The location was also a convenient base for seeing Tuscany, and we had a great meal nearby in Rapolano Terme. Overall, it has the potential to be one of the coolest places you'll ever stay, though we did encounter a few technical issues regarding the shower and WiFi (which the hosts were quickly responsive about). I'd still recommend it, but it's helpful if you go in...
United Kingdom
Kevin
The price is 2.696.560 ₫
3.081.939 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Podere La Chiusella
A terrace with a table set for breakfast, overlooking a scenic landscape.

14. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (48 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is 4.899.708 ₫
5.505.518 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Delcorto Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

15. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is 2.272.306 ₫
2.615.260 ₫ total
includes taxes & fees
4 Nov - 5 Nov
TuscanyLettings Studio&Room
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 San Gregorio

Hotel San Gregorio

10/10 Excellent
"Get"
Taisa 1-night trip
Posted 3 hours ago
Hotel San Gregorio

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 11 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. The International Kitchen - Classic Tuscan Table and Golf Club Valdichiana are other places to visit while you're in town.

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.