Cortona Guest Houses

A hillside town with historic buildings, a church, and vineyards.

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Our top choices for Cortona guest houses

A courtyard with stone buildings, a gravel path, and potted plants.

1. B&B San Francesco

Cortona Old Town

Esther

RM451 total

includes taxes & fees

5 Oct - 6 Oct

A stone building with multiple windows and a central entrance.

2. Fondaco del Moro

Civitella in Val di Chiana

Heather

RM310 total

includes taxes & fees

5 Oct - 6 Oct

A stone staircase with red steps leading up to a building.

3. Villa Sargiano

Arezzo

"If you love nature, that's the perfect place to enjoy and relax. The property has all the amenities for families with kids: - space inside and outside - pool (opened during the summer season) - Kitchen - TV - air condition and heating system working properly and even together if needed. This always keeps the temperature you want. The property owner is flexible during the check-in time, very friendly and wants to guarantee you have the best experience staying in his Villa. The welcome bottle of...

Giuseppe

RM634 total

includes taxes & fees

11 Oct - 12 Oct

A restaurant with brick arches, wooden tables, and chairs. There are wine bottles on a shelf and a hanging light fixture.

4. Palazzo Mosela Alla Porta

Montepulciano

Kerry

RM594 total

includes taxes & fees

2 Nov - 3 Nov

A table set with a bottle of wine, two wine glasses, and a vase with flowers.

5. Poggio Paradiso Resort & Spa

Torrita di Siena

Giulio

RM970 total

includes taxes & fees

3 Nov - 4 Nov

A room with a glass floor, stone walls, and a door in the center.

6. SUGAR ROOMS Residenza d' Epoca

Arezzo Centro Storico

Shelly

RM924 total

includes taxes & fees

17 Oct - 18 Oct

A staircase with a patterned carpet and a wooden handrail.

7. Palazzo Ninci

Civitella in Val di Chiana

Maurizio

RM290 total

includes taxes & fees

5 Oct - 6 Oct

A view through an arched window of a historic building with a bell tower, a courtyard, and surrounding architecture.

8. La Corte del Re Suite & Rooms Arezzo

Arezzo Centro Storico

Amy

RM386 total

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a bed, a ceiling fan, a desk, a chair, a TV, and a window with blinds.

9. Santo Spirito

Saione

Ariel

RM313 total

includes taxes & fees

12 Oct - 13 Oct

A two-story building with a brick facade, multiple balconies, and a courtyard with outdoor seating.

10. Piccola Siesta b&b

Montepulciano

Darren

RM391 total

includes taxes & fees

5 Oct - 6 Oct

A staircase with a brick archway, a painting of a field, and a door with a window.

11. MontepulcianoLettings

Montepulciano

"The property is extremely well located near the start of the old town and was walkable to everywhere. Our room was small but very lovely and when we stuck our heads out of the window, we had an amazing view of the old town! The only problem was parking - we couldnt find any bc of a festival - but thats not the hotels fauot! Just be a bit organsjed - and i recommend parking behind the bus terminal (Eu10 per day)."

Charmaine

RM453 total

includes taxes & fees

1 Nov - 2 Nov

A patio with two lounge chairs, a small table with a pitcher and glasses, and a decorative fence.

12. San Bartolomeo LT

Passignano sul Trasimeno

Per

RM883 total

includes taxes & fees

5 Oct - 6 Oct

A pool area with lounge chairs and umbrellas, surrounded by a well-maintained lawn and a large building in the background.

13. Domus Volumnia Country House

Perugia

Nadia

RM452 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a courtyard, a small fountain, and a tree.

14. Antica Quercia & Spa

Chianciano Terme

Anaïs

RM381 total

includes taxes & fees

1 Nov - 2 Nov

A multi-level outdoor patio with a staircase, seating areas, and potted plants.

15. Residenza il Punto

Perugia

Simone

RM634 total

includes taxes & fees

5 Oct - 6 Oct

A hotel entrance with a sign reading "TIMES SUITES & BAR", a staircase leading inside, and two potted plants.

16. Times Suites Guesthouse - Etruria Collection

Old Town Perugia

Ariel

RM502 total

includes taxes & fees

25 Oct - 26 Oct

A courtyard with a brick pathway, a stone building, and a glass structure with warm lighting.

17. Anna Boccali Resort

Corciano

Jacob

RM1,022 total

includes taxes & fees

5 Oct - 6 Oct

A stone-walled room with a fireplace, a table with chairs, and a hanging light fixture.

18. Borgo Nuovo San Martino

Bucine

Josimar

RM494 total

includes taxes & fees

1 Nov - 2 Nov

A table set for two with a bottle of wine and glasses, overlooking a scenic landscape with hills and trees.

19. Castello Di Petroia Relais

Gubbio

Emma

RM734 total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bunk bed, a bedside table with a lamp, a TV mounted on the wall, and a view of the outside balcony.

20. Il Bacio - Guest House

Perugia

RM630 total

includes taxes & fees

20 Oct - 21 Oct

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Top Cortona Hotel Reviews

B&B San Francesco

8/10 Good

"We loved the property and the atmosphere The staff went over and beyond to help us navigate our arrival but even with this help we found it difficult to to navigate our arrival because of our larger car size and Google Maps Online apps do Not work here. Thank goodness for our host’s instructions"

Hotel Italia

10/10 Excellent

"This small quaint hotel absolutely MADE my trip to Italy!! I will never forget the kindness shown to my friend and me ~ we were instantly made to feel at home and felt like we were treated like their "special guests"! The hotel was so endearing. So charming. The view from my room was magnificent ~ I'm sure I took 200 photos just from my window! The included breakfast upstairs with practically a 300° view looking over the landscape and rooftops was delicious. It was a wonderfully calm way to start each day there; I could have wasted much of my time there, just soaking up the view, the colors, the atmosphere and the friendly staff ~ all the while sipping my tea :-). The hotel is not overlooking the noise of the bustling square, but just a few steps down a cobbled street and you are at their front door...not even a one minute walk, but a much quieter setting....should one appreciate that as I do. Just writing this, I'm thinking "I'm not sure I'll ever in my life be blessed to make it back to Italy, but if I am, I have no doubts where I'll be staying!" My stay was in the heat of August of 2026... The owners said to come back at Christmas ~ as it is "really, really something at Christmas time!" I'm not sure how it could be better, but one year I hope maybe I greet them again and find out!"

Locanda agli Amici

10/10 Excellent

"This was the perfect away from the city stay for us. Cortona was just a quick few day stay for us but the staff/sylvia were fantastic. Room was clean, the breakfast was delicious. A/c and water pressure from the shower was much needed and the location was perfect for us. It is a short walk from downtown Cortona (steep walk into the city and about 15 mins) but the views are unmatched. Sylvia went above and beyond for us picking us up and dropping us off at the bus station. Highly recommend to anyone visiting Cortona."

Hotel San Michele

8/10 Good

"This is a charming hotel housed in a 15th century palazzo as close as you can get to the center of Cortona. The staff was pleasant and helpful. Plus you can pull your car up for luggage drop off - a real convenience in a town center where cars are otherwise restricted. Just note this hotel is in an old building. Not all rooms are serviced by elevator - some stairs required. And like any historic property the facilities have charming quirks - rooms but not all public facilities have A/C, lighting is low and there are no amenities on site other than a lovely buffet breakfast you can enjoy inside or in a garden setting. However its location steps from Cortona’s Piazza Republica, restaurants and shops make up for any shortcomings!"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

Find out more about Cortona