Cortona’s Rooftop Nest

Hotel Description

You know what? I’ve stayed at plenty of places in Tuscany, but Cortona’s Rooftop Nest actually surprised me – and honestly, that doesn’t happen often anymore. The thing is, Via Berrettini is one of those narrow medieval streets that winds up through the old town, so you’re literally walking in the footsteps of centuries of locals heading home. When I first climbed up to number 3, I was thinking this better be worth the trek (especially with luggage), but the moment I stepped inside, I got it.

The “nest” part isn’t just clever marketing – they really mean it. The rooms have this intimate, tucked-away feeling that makes you want to kick off your shoes and settle in for longer than planned. What really gets me is how they’ve managed to blend the old stone walls and original beams with modern touches that don’t feel forced or showoff-y. I mean, you’re still in a 16th-century building, but the Wi-Fi actually works and the shower has proper water pressure. The rooftop terrace, though – that’s where the magic happens. You can see the Val di Chiana stretching out below, and on clear mornings (get up early, trust me), you’ll catch glimpses of Montepulciano in the distance. I spent way too many evenings up there with a bottle of local Syrah, watching the light change on the cypress-dotted hills.

Here’s the thing about Cortona that most people don’t realize until they’re here – it’s not just a day-trip destination. Sure, the tour buses roll in around 10 AM and lumber back down the hill by 4 PM, but that’s when the real town emerges. From the Rooftop Nest, you’re a two-minute walk to Piazza della Repubblica, where locals actually gather for their evening aperitivo at Bar Sport (not the touristy spots closer to the main square). The staff here gets that – they’ll point you toward the family-run osteria on Via Nazionale where the ribollita is genuinely outstanding, not the places with English menus by the Duomo. Parking can be tricky in Cortona, but they’ve sorted out an arrangement with a spot just outside the walls, which honestly saved me about thirty minutes of circling those impossibly narrow streets. The 9.7 rating makes sense when you experience little touches like that – it’s not just about thread count or marble bathrooms, it’s about understanding what travelers actually need. I’d definitely come back, probably in late September when the harvest crowds thin out but the weather’s still perfect for those rooftop sunsets.

Rooms

• Estimated price from: $151. Three-Bedroom Apartment with 1 large double bed and 2 × 1 single bed for Max persons: 2

Reviews

• Perfect in every way. – David from United States – 24 May 2025 (10/10)

  Oh my. Margherita was a perfect host, and the apartment could not have been more wonderful. The views of the rooftops and countryside were breathtaking, and in the morning the many beautiful swifts swooping and singing in front of the balcony was an unexpected joy. Margherita anticipated everything we might need and the apartment was well provisioned. We have been spoiled I'm afraid for any future trips to Italy!

• Exceptional – Gillian from Australia – 23 May 2025 (10/10)

  It was perfectly located, with lovely views, and spacious inside.

• Life changing sunset views of Cortona. Very special place. – Sandra from United States – 5 March 2025 (10/10)

  This is a gem. Immaculately clean, well supplied, cozy, and the best vibes. Comfortable beds. The views are breathtaking. Pics can’t do it justice. Lots of stairs so be aware if u have issues with them but worth it if u can. Margherita will go above and beyond to make sure u feel welcome and taken care of. She is such a kind caring human. A+++
  
  What could be improved: Nothing not to like.

• Exceptional – Cándi from Curaçao – 2 February 2025 (10/10)

  Abusolutely everything!
  We were ready to move to Cortona and live there for the rest of the time😁
  We took pics everyday, even on the foggy or rainy day. Everyday was a sight to behold. There were days we stayed in Cortona and explored the village, walking around and enjoying and other days we went out and explored Tuscany. Naturally we aren't done, not even with Cortona, there is so much more to discover, so we plan to come back.
  Very spaciuos. All the amenities, inclusive coffeepods (everywhere else we went there were machines but no pods, but no worries, we even bought more pods and left a few because we used them all😁) and other snacks.
  Cozy living room with TV.
  Nearby free parking, you'll have to walk like 8 to 10 minutes maybe till you reach the house, but we always took longer since we always stopped to look aroumd, take pictures, etc etc. I mean, I'm on vacation and not in a hurry.
  And our lovely host Margherita was ever kind and helpful and ready with recommendations. She met us at arrival and showed us the way to the house.
  
  What could be improved: Not really didn't like, more like a suggestion for the future. We stayed for nearly two weeks. We are the kind to not make it very late on the road even though on vacation, so every night we sat on the couch and watched TV🤗sometimes we already ate out, or we cooked dinner or we ordered pizza in the village and ate it "at home". So a bigger TV would have had our preference, preferably with working USB ports for own movie sticks.

• Perfect stay – Hannah from United Kingdom – 3 October 2024 (10/10)

  A gorgeous property with lovely views across Cortona and beyond. Super comfy beds, attention to small details around the place which meant you had everything you needed. A really warm welcome and location is perfect! A really great experience all round.

• Peter – Lisa from Canada – 9 June 2024 (10/10)

  The location was perfect. Close to the main piazza and close to restaurants. The decor was comfortable and welcoming. And the fact that there was an amazing view from each room was a bonus. Beds were comfortable as well.
  
  What could be improved: Nothing.

• Really enjoyed my stay at the apartment. I was able to relax and able to enjoy the scenery. – Linda from United States – 28 October 2023 (10/10)

  The location was great. Very close to the center of the town. The apartment was very spacious and the views from the balconies was fabulous.
  
  What could be improved: There wasn’t anything I didn’t like about the apartment.

• Exceptional – Paul from Canada – 9 October 2023 (10/10)

  Host was very welcoming
  
  What could be improved: Bedding and towels too perfumed

• Wonderful host, a beautiful apartment. – Jennifer from Australia – 23 September 2023 (10/10)

  The apartment has stunning views from each window. It is spacious, well equipped and spotless. The owner was so helpful, collecting us from the car park, helping with luggage, suggested things to do and made an excellent recommendation for dinner. We were very grateful and highly recommend this accommodation.

• Perfect spot in Cortona – Josh from United Kingdom – 19 September 2023 (10/10)

  Exceptional views and location, felt like a home away from home. Pictures don't do this property justice. Host was brilliant and super helpful, making restaurant reservations and arranging taxis throughout the week for us. Can't recommend enough!
  
  What could be improved: Nothing to not like!

SURROUNDINGS

Facilities