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Villa il Padronale
Villa Santa Maria Nuova

Your Perfect Retreat Awaits

Experience the Finest Homes in Cortona

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Hill Town Tours has a huge selection of breathtaking properties in Cortona, Tuscany, the heart of Italy. We directly own and exclusively manage all our villas and apartments, providing the highest quality service. Explore our selection of luxurious properties and book the perfect accommodation as the base for your dream trip to Italy.

80+

Villas & Apartments
in Cortona, Tuscany

15+

Years of experience
 

Villa or Apartment?

FIND YOUR STUNNING HOLIDAY HOME

Wether you are coming with family and friends, or just as a couple, we offer an impressive array of villas and apartments to suit your needs. From 1 bedroom apartments to 8 bedroom villas, you can find the perfect fit for your family and friends in the most beautiful area of Tuscany!

Villas Apartments

Villas

Up to 12 Guests
Up to 9 Bdr

Charming villas in Cortona, Tuscany, offer a perfect blend of rustic elegance and modern amenities. Enjoy stunning views, private pools, and peaceful surroundings, ideal for a relaxing getaway.

  • Exclusive outdoor space
  • Privacy
  • Ideal for groups

Apartments

Up to 6 Guests
Up to 3 Bdr

Charming vacation apartments in the heart of Cortona, Tuscany, offering a perfect blend of rustic charm and modern comfort. Ideal for exploring the town's rich history and beautiful landscapes.

  • In town experiences
  • Walking distance to everything
  • Great for couples or families

Hill Town Tours

OUR REVIEWS ON

Hill Town Tours coordinated our trip to Cortona and Tuscany. They made arrangements for a stay in a gorgeous villa with incredible views, a sparkling, clean pool, and well equipped kitchen. We were treated to an Italian cooking lesson at home in the Villa and finally they coordinated our reservations at one of the hardest to get restaurants in Cortona, AL TOCCO, where we had the best meal of our entire trip and one of the best meals ever! The service was incredible.
The food fantastic. We went with the chefs tasting menu with wine pairing and could not have been happier.

kathygX5623LT

Wonderful Tuscany villa experience with amazing hosts that helped make the week one of the best vacations. Large villa offered relaxing privacy surrounded by beautiful landscape with incredible sunsets. Villa was a short drive to many of the must see towns, restaurants, and wineries of Tuscany. Our vacation was made easier with the breakfast provided daily in villa option, had lots of fun with the HTT winery tours ( the smaller Baldetti winery was a great way to start one day of tours), and we even learned to make pasta with an in villa cooking class! Strongly recommend the HTT experience- and hope to repeat it again soon.

C S

What a wonderful week we've had at Villa Torre delgi Elci!! The villa was very spacious and accommodated 2 families (one with 3 teenage children and the other with 2 toddlers) with ample room to spare. The HTT team were superb and looked after us so well. A special mention to the housekeepers who made us delicious breakfast every morning. We also loved the outdoor kitchen and dining area - the pizza oven and BBQ was well used! The view to was amazing with lovely evening drinks watching the sunset on the garden wall. We made some lovely memories this holiday and can't wait to be back!

Chilliecider

We highly recommend Hill Town Tours in Cortona! The house was gorgeous. The views were unbelievably beautiful. The in home chef, Gabriele, was the best part of our trip. We were so excited to see him at the end of every day. He created unique, Tuscan meals every night of our stay. Every course was delicious. He gave us insights into Tuscany and was a wealth of information. Hill Town Tours scheduled several activities for us (in addition to our nightly chef) and each experience was wonderful from ruffle hunting to cheese making to wine tours. I highly recommend this company and their properties. Everyone was very professional and all of their excursions were top notch. The in home grocery service upon our arrival was super helpful and well organized.

Lynn L

We had the most amazing experience in Cortona at the Villa Antica Mulina. We stayed 7 nights. Our wonderful driver Filippo picked us up each day for a new adventure and always had great ideas about where to go and what to see. Daniella lovingly prepare our breakfast each morning and it was delicious! Chef Roberto stopped by one night to teach us how to make gnocchi and we also made the most delicious strawberry tiramisu. Jonathan and Liana in the office were terrific for the advance planning part of the trip. We will definitely go back and I would love to experience this with an even bigger group of friends or couples. Highly recommend.

Lori G

We rented a villa for a week in Cortona with Hill Town tours and it was amazing. Thank you Alessandra for making the best breakfast every morning, we were spoiled and dinner too! You are the best and we will miss you. And thank you Gabrielle for teaching us how to make pasta. The trip wouldn’t have been the same without you two. Will be back to Cortona! The property was incredible and very well maintained. Only advice is that if you are driving to the property request to drive behind someone from hill town tours or request a pick up. The roads up the mountain are narrow and windy and Google maps doesn’t guide you the right way. They came to our rescue when we were lost. Grazie.

Nora Z P

Wow!! Excellent location and the Villa was amazing—the owners should be very proud of this great vacation home—cudos to Hilltop Tours for all the events we planned with you and special Grazie to Denise and her mom for the Breakfast each morning-Belissimo!! Alesandre-pasta making etc was so much fun-cheese making with Fattoria Bistecca-Iliry and Lapo —winery’s were absolutely the best choices—all the wine we didn’t ship made it back unscathed  We can’t wait to plan a return visit in the future—again Thank you all for the Grande experience!!
Ciao

Robert Sariano

We were in a four-storey centrally located Cortona apartment with all the mod cons you’d expect. Be aware you’re in the heart of a working Medieval town with occasional whiffy drains, regular church bells, locals chatting in the street so avoid if you’re looking for total tranquility. We liked the hustle and bustle and being within easy walking distance of all the attractions. Everything worked although we didn’t use the windowless sitting room as it’s more of a cool space for escaping summer heat rather than early spring. Hill Town tours were responsive to all our questions and offered plenty of suggestions for outings and activities.

Peter Robertson

We had a FABULOUS experience with Hill Town Tours when we stayed with 2 other couples at a Villa in Cortona. The communication leading up to the trip was spot on. Check in was seamless and a representative met us at the property. The Villa we rented was amazing. Beautifully furnished, comfy bedroom and en suites and well equipped kitchen. The outdoor patio areas were breathtaking. Hill Town was available arranged a private chef and several wine tastings.They gave us great recommendations and answered every last questions. We have traveled the world and many times to Italy. This was a FIVE star experience for sure. We will gladly recommend Hill Town again and hope to return to the heavenly town of Cortona.

Lesa Stuart

We stayed at the Le Corchie villa in Cortona for 7 days in April 2022 and were very pleased with the accommodations. Great views and enough space for 8 of us (4 couples). We had Daniella as our daily chef and she was fantastic and incredibly helpful with anything. The meals were fantastic . We also had. Riccardo as our driver and he was superb. His English was very good and his company all week was welcomed and appreciated. Very accommodating to our on-the-whim trips to the store or elsewhere. Daniella and Riccardo made our Villa stay worthwhile. The only thing missing was a clothes dryer, but we all managed ok. 

Rich J. L.

Hill Town Tours

OUR KEY FEATURES
Book Direct
with HTT

When you book an accommodation with us, you book directly. We own or exclusively manage all our villas and apartments, giving the best and most direct service possible.

Local
Staff

HTT employs a large team that handles every aspect of your trip. We are local to Cortona and have the best knowledge and experience of the area. Our dedicated staff will provide you with the top information and service.

Exclusive
Services

We have thought of everything for you and provide it all! Our team consists of reservation & concierge specialists, private chefs, housekeeping, private drivers, tour guides, and more!

Highest
Quality

From our accommodations to our services, quality is our top priority. We make sure every aspect of your vacation is truly the best and we are dedicated to providing the highest quality and standards out there.

Go Bespoke

ENJOY YOUR STAY!

Want a special, once-in-a-lifetime experience? HTT can customize your dream vacation and make that dream a reality with our bespoke services tailored to your desires.

Interested in visiting other cities in Italy as well? We can plan a trip for you to the best destinations in Italy, such as the Amalfi Coast, Lake Como, Rome, Sicily, Venice, and more! Our dedicated reservations team is equipped with all the best knowledge to make your trip truly memorable!

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