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

Sinalunga Holiday Rentals

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Our top choices for Sinalunga holiday rentals

1. Studio Apartment "Il Colle dei Frati" with Private Terrace & Wi-Fi

Studio Apartment "Il Colle dei Frati" with Private Terrace & Wi-Fi
Sinalunga
10.0 out of 10, Exceptional, (2 reviews)
"Pros: La casa affaccia su un bel giardino e una meravigliosa vista panoramica sul paese e su tutta la Valdichiana. Si respirano tranquillità e si possono ascoltare cinguettii e suoni della natura. La proprietà possiede tutti i comfort, proprio come a casa. L'ambiente è molto spazioso, pulito e profumato: si può godere di tanta tranquillità e anche della disponibilità e simpatia dell'host, la signora Gabriella e dei suoi gatti Rocco & Rocco."
Italy
Anonymous traveller
The price is NZ$224
includes taxes & fees
28 Sept - 29 Sept
Studio Apartment "Il Colle dei Frati" with Private Terrace & Wi-Fi

2. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (70 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is NZ$311
includes taxes & fees
7 Oct - 8 Oct
Il Poggio dell'Eremita

3. Cozy apartment with an outdoor terrace in the heart of the Val di Chiana

Cozy apartment with an outdoor terrace in the heart of the Val di Chiana
Sinalunga
The price is NZ$324
includes taxes & fees
17 Oct - 18 Oct
Cozy apartment with an outdoor terrace in the heart of the Val di Chiana

4. Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning

Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning
Scrofiano
The price is NZ$406
includes taxes & fees
30 Sept - 1 Oct
Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning

5. Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi

Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
Scrofiano
The price is NZ$777
includes taxes & fees
28 Sept - 29 Sept
Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi

6. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is NZ$228
includes taxes & fees
28 Oct - 29 Oct
Abbadia Sicille Relais

7. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is NZ$254
includes taxes & fees
8 Oct - 9 Oct
Affitacamere Maria Gabriella

8. 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 NZ$167
includes taxes & fees
28 Sept - 29 Sept
Artisti del Cavallo Tourism

9. 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 NZ$170
includes taxes & fees
30 Sept - 1 Oct
Villa Fontis Rapolano

10. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is NZ$320
includes taxes & fees
8 Oct - 9 Oct
Meublé Il Riccio

11. 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 NZ$252
includes taxes & fees
19 Oct - 20 Oct
Castello di Modanella

12. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 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 NZ$161
includes taxes & fees
8 Oct - 9 Oct
Residenza Fabroni

13. Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is NZ$431
includes taxes & fees
6 Oct - 7 Oct
Luxury resort in the Tuscan countryside

14. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 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 NZ$247
includes taxes & fees
14 Oct - 15 Oct
Bed & Breakfast Vicolo dell'Oste

15. 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 NZ$213
includes taxes & fees
4 Oct - 5 Oct
DormiVeglia B&B

16. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is NZ$294
includes taxes & fees
28 Oct - 29 Oct
Hotel San Gregorio

17. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is NZ$559
includes taxes & fees
14 Oct - 15 Oct
Fontelunga Hotel & Villas

18. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (148 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is NZ$424
includes taxes & fees
12 Oct - 13 Oct
La Locanda di San Francesco

19. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (44 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is NZ$381
includes taxes & fees
28 Oct - 29 Oct
Delcorto Suites

20. 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 NZ$209
includes taxes & fees
18 Oct - 19 Oct
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

Find out more about Sinalunga

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sinalunga holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sinalunga. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sinalunga. Seeing all the best attractions is bound to make you fall in love with Sinalunga. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sinalunga short-term rentals, that won’t be hard to do.

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.

What are some of the best holiday rentals that Sinalunga has to offer?

Borgo Argiano: This holiday home rental outside of Sinalunga 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 kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Sinalunga?

With 10 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. Golf Club Valdichiana and The International Kitchen - Classic Tuscan Table 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.