This is a toplist with the best hipster hotels in Cortona, Italy. You can help to make this list better by voting for your favourite places!
1 Monastero di Cortona - Hotel & Spa
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We had stayed here a while back just after the renovations and had the most incredible time. From the moment we walked in and even before the staff were so wonderful and helpful; the service was phenomenal! As we had arrived quite late into the beautiful town of Cortona, the staff were so kind as to book us a last minute reservation at a top restaurant in town! They were so helpful with giving us suggestions of what to see and booking wine tours for us. They really went above and beyond to make our trip time in Cortona so memorable! This was one of the most beautiful places I’ve ever stayed, the attention to detail and views were fantastic! Will most definitely be coming back to this fantastic place!
3 Hotel Villa Marsili



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Spent 2 night here September 2019. Beautiful hotel, well appointed rooms, super friendly and helpful staff. The provided breakfast was varied and sumptuous! Location in Cortona was perfect, right outside the city walls. We would definitely stay there again.
4 Hotel San Luca



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Tonight we marched on the beautiful mountain top town of Cortona, made famous by the movie "Under the Tuscan Sun"..... mamma mia nose bleed to drive up here. I Should have turned down Hertz for upgrading me for free to such a large car! Outside escalators up the parking spot to Hotel... breath taking views from our balcony room. Later.... now we march! Wonderful Hotel San Luca. Pinch me.
5 Hotel Italia



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Just arrived home after 5 day’s in Cortona hotel Italia is a stunning building In a beautiful area of Tuscany hotel was more than comfortable well heated as it is winter friendly staff plenty of choice at breakfast cereal fruit yogurt pastries meat and cheese I’d recommend this hotel to anyone and will definately be returning
6 B&B Piccolo Hotel



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Amazing staff - were really helpful and gave us great recommendations (specially Matteo who recommended a brilliant ice-cream place and places to find vacuum-sealed cheese). Thanks to them we were able to load up and enjoy Italian cheese for months to come!
The location is unbeatable - literally seconds away from the main square with none of the noise to match! They also had free private car parking and valet from the hotel door.
The only downside would be breakfast, which wasn't the best, but that's very Italian and didn't affect our stay. Would definitely come back next time we're in Cortona!
7 Hotel Sabrina



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What a beautiful place. Original features. Just want you want for an authentic experience. Amazing service and very friendly and welcoming
8 Cortona Suite B&B



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I stayed her with my wife on our honeymoon. I would highly recommend it. It is a great location in the heart of Cortona. The host is friendly and very pleasant to deal with. She clearly pays attention to detail and provides an amazing breakfast to the room. It is a medieval building without a lift, so be prepared to carry your luggage up the stairs.
10 Casa Dreosti. Boutique accommodation



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Beautifull boutique B&B. Rooms are well equipes and have airconditioning. Jeroen, the host, is very friendly. He knows the best places to be in Cortona! The b&b is in the center of Cortona.
11 Le Bifore



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A Beautiful boutique hotel overlooking the Tuscan valley. The location is perfect for a short stay, right in the centre of town and the staff are so lovely. You couldn’t ask for a comfier bed. Only downside is you can’t check in before 2pm.
12 The Court of Ambra B & B Luxury in Cortona



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Yes you must stay here. The decor perfectly matches the history or Cortona. The owner Sara if friendly and very helpful. Cortona is amazing and a must visit in Tuscany.
13 B & B Casa Kita



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Best prices for a bed and breakfast style. Treated us like family and served us a gormet meal on our last night for no extra charge. Close to everything and best view around. Quiet. No air conditioning, no English. Speaks Spanish and Italian.
14 Cortona Charme



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Beautiful apartment located in the heart of the town with a breathtaking view of the Valdichiana.
16 B & B Dolce Maria



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The best dishes from Tuscany with many local specialities. Fantastic service from the staff, everything is done with great enthusiasm. Very welcoming atmosphere ! So far our go to restaurant in Cortona.
19 Relais Villa Baldelli



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I absolutely loved this Villa! Staff was amazing, the entire place is unreal, really worth spending couple of days here. I highly recommend it and I can't wait to return!
20 Il Nido di Turan



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Room for 4 really spacious and clean. Hearty breakfast, albeit bound by covid rules. Friendly and helpful owner. The only flaw is the lack of a window from which good light can enter, so the room remains rather dark.
I try to keep this list very up to date. It was last edited in January 2025. You can help me make this page better, for example by letting me know of a hipster hotel that should be on the list. Click here to get in touch. Thanks!