Top 10 Hotels in Cesa in 2026 (from $69)

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A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

A restaurant interior with tables set for dining, a kitchen area, and a wine display.

A hotel lobby with a brick archway, a reception desk, and potted plants.

An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.

1. Hotel Le Capanne

Arezzo

$117

$135 total

includes taxes & fees

Oct 12 - Oct 13

A stone building with multiple windows and a central entrance.

A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.

A dining area with a table set for two, white chairs, and a stone-patterned floor.

A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.

2. Fondaco del Moro

Civitella in Val di Chiana

$70

$77 total

includes taxes & fees

Sep 29 - Sep 30

A tranquil sunset over a calm body of water with a gazebo structure in the foreground.

An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.

A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

3. Cortona Resort - Le Terre Dei Cavalieri

Cortona

$134

$153 total

includes taxes & fees

Sep 29 - Sep 30

A restaurant with glass walls, tables set with white tablecloths, and chairs.

A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.

A skylight with a view of a tree and a distant building.

A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.

4. La Cantina Relais - Fattoria Il Cipresso

Arezzo

$101

$117 total

includes taxes & fees

Oct 12 - Oct 13

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

A modern hotel lobby with a large mirror, potted plants, and a spacious seating area.

A hallway with a decorative archway leading to a door, a row of plants on the left, and a wall-mounted lamp on the right.

A rooftop terrace with outdoor seating, a pergola, and a view of hills.

5. Il Gentiluomo Hotel & SPA

Arezzo

$74

$88 total

includes taxes & fees

Oct 1 - Oct 2

A modern hotel lobby with a reception desk, seating area, and a large plant.

A hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.

A modern bar area with a counter, bar stools, and a seating area with chairs.

A modern library with leather sofas, bookshelves, and a large window.

6. Hotel Park

Castiglion Fiorentino

$107

$122 total

includes taxes & fees

Oct 1 - Oct 2

An outdoor patio area with wicker furniture, a table, and a lamp.

A bar area with a variety of liquor bottles, a pizza on a wooden board, and three martini glasses with straws.

A room with a white counter, a bowl of fruit, a plant in a gold pot, and a mirror reflecting a plant and a window with curtains.

A hallway with a wooden floor, a small table with a vase, and a light fixture on the ceiling.

7. Il Monte

Monte San Savino

$74

$114 total

includes taxes & fees

Oct 1 - Oct 2

An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.

A bedroom with a large bed, wooden headboard, a chandelier, a nightstand, and a red rug.

An outdoor dining area with string lights, tables set for a meal, and a natural backdrop.

A window with a view of a green landscape, a table with a teapot, cups, and a tray of snacks.

8. Podere La Rocca

Montepulciano

$158

$178 total

includes taxes & fees

Oct 25 - Oct 26

A rustic outdoor dining area with stone walls, a table, and wicker chairs.

A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.

A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.

A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

9. Relais Villa Baldelli

Cortona

$128

$150 total

includes taxes & fees

Sep 29 - Sep 30

An outdoor dining area with tables and chairs under canopies, surrounded by greenery and a building with a tiled roof.

A large outdoor swimming pool with multiple lanes and a surrounding deck area.

A hotel room with a bed, bedside table, and a desk with a chair.

A room with a wooden desk, a laptop, a chair, a sofa, and a small table with a bowl of fruit and flowers.

10. Hotel Apogeo

Sinalunga

$101

$113 total

includes taxes & fees

Oct 2 - Oct 3

A stone building with outdoor seating and a fountain.

A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.

A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.

A stone building with a tiled roof, a small window, and a metal fence.

11. Villa Borgo San Pietro

Cortona

$117

$137 total

includes taxes & fees

Oct 5 - Oct 6

An outdoor dining area with a table set with food and wine, surrounded by outdoor seating and a large house in the background.

A courtyard with a brick building, surrounded by well-maintained lawns and potted plants.

A restaurant with round tables set for dining, large windows with curtains, and a view of the countryside.

A pool surrounded by neatly trimmed hedges and a row of sun loungers.

12. Borgo Tre Rose

Montepulciano

$74

$86 total

includes taxes & fees

Oct 24 - Oct 25

A dining area with a table and chairs, large windows with curtains, and a view of a landscape.

A window view of a town with buildings, trees, and parked cars.

A balcony with two lounge chairs, a small table with a drink, and a scenic view.

A hotel room with a large bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.

13. Hotel San Luca

Cortona Old Town

$81

$98 total

includes taxes & fees

Oct 25 - Oct 26

A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.

A bedroom with a stone wall, a bed with a headboard, a desk with a computer, a chair, a window with a view, and a ceiling with exposed beams.

A restaurant with outdoor seating overlooking a historic town and the sea.

A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.

14. Hotel Italia

Cortona Old Town

$132

$151 total

includes taxes & fees

Oct 28 - Oct 29

A modern interior with a piano, dining area, and a large decorative animal statue.

A hotel gym with stationary bikes, a treadmill, and dumbbells.

A reception desk with a modern design, a flat-screen TV, and a glass partition.

A hotel room with a large bed, two bedside tables, a desk, a chair, and a window with curtains.

15. B&B Hotel Arezzo

Arezzo

$58

$71 total

includes taxes & fees

Oct 18 - Oct 19

A stone building with outdoor seating and a pool in the background.

A bedroom with two beds, a chandelier, a leopard-print chair, and a small table with a vase.

A dining table set with various foods, including meats, cheeses, and fruits.

A stone house with a paved driveway and a lawn, surrounded by trees and a white car parked in front.

16. B&B Country House Poggio del Drago

Civitella in Val di Chiana

$106

$116 total

includes taxes & fees

Oct 11 - Oct 12

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

A cozy living room with a sofa, armchair, and a coffee table with a vase.

An open door leading to a balcony with a stone wall and a view of a landscaped garden.

A hotel room with a bed, a sofa, a chair, a small table with a lamp, and a window with a view of a green landscape.

17. Poggio Paradiso Resort & Spa

Torrita di Siena

$268

$300 total

includes taxes & fees

Oct 28 - Oct 29

A kitchen with a brick archway, a wooden table with pies, and a clock on the wall.

A modern interior with a staircase leading to a loft area, a dining table with chairs, and a television in the background.

A modern kitchen with a wooden countertop, white appliances, and a backsplash of blue tiles.

A breakfast table with a variety of food items, including pastries, cereal, and juice, along with cups and a spoon.

18. A Casa di BiaGio B&B

Rapolano Terme

$105

$120 total

includes taxes & fees

Sep 30 - Oct 1

An outdoor dining area with tables set for a meal, surrounded by stone walls and potted plants.

A yellow building with a stone wall and a swimming pool reflecting the building and trees.

A yellow building with stone walls and multiple windows with shutters.

19. Palazzo Tiglio - A Small Luxury Hotels of the World

Bucine

$254

$284 total

includes taxes & fees

Oct 17 - Oct 18

A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.

A buffet table with various food items, including cookies, pastries, and dairy products, with labels indicating gluten-free options.

A spacious room with a fireplace, multiple seating areas, and large windows allowing natural light.

A balcony with potted plants and a view of the sea.

20. Villa Santa Margherita

Cortona Old Town

$117

$134 total

includes taxes & fees

Sep 29 - Sep 30

View all properties

Go beyond your typical stay in Cesa

Check out reviews of Cesa hotels guests love

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Exceptional

Steve

Cortona Resort - Le Terre Dei Cavalieri

Cortona

10/10 Exceptional

Words cannot describe the amazing experience at 'Le Terre dei Cavalieri'. The place is so unique and full of character and history, the surroundings are amazing, with an excellent Restaurant in house. The resort is a few minutes away from two beautiful towns like Cortona & Montepulciano. For the shopaholics it is just a 15 minutes dive from a very good Outlet Village. Our stay was made even more special with the help of the personnel, everyone was so helpful and accommodating, especially...

Mario

Podere La Rocca

Montepulciano

10/10 Exceptional

Our stay at Podere La Rocca was fabulous! The property is located in the rolling Tuscan hills just outside Montepulciano. The property is a working farm and vineyard with an onsite restaurant and pool. Our room was comfortable and clean. The bathroom was huge with a new jetted tub. We stayed on the second floor in a building with a large communal room with a fireplace. On the first floor of the same building was a rec room with a pool table. What made the stay was our experience at the...

Poggio Paradiso Resort & Spa

Torrita di Siena

10/10 Exceptional

Paul

A terrace with sun loungers, stone walls, and potted plants.

A pool area with lounge chairs, a hot tub, and a view of mountains.

A narrow hallway with a stone wall and a clock.

A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Exceptional

Eric

Relais Villa Baldelli

Cortona

10/10 Exceptional

Lizette

A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.

A hotel room with a fireplace, two armchairs, a bed, and a dresser.

A spacious living room with a yellow sofa, a wooden coffee table, and a floral rug. There are two armchairs and a dining table with chairs. The room has a large window with curtains, a mirror, and wall-mounted lights.

A table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

Hotel Villa Marsili

Cortona Old Town

10/10 Exceptional

Kim

Villa Santa Margherita

Cortona Old Town

10/10 Exceptional

George F

Hotel Park

Castiglion Fiorentino

10/10 Exceptional

Jean

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Exceptional

Kristen

A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.

A person in a swimming pool with a view of trees and mountains through a window.

A person standing at the entrance of a building with a stone staircase leading up to a door.

A spacious, well-lit restaurant with large windows, wooden tables, and potted plants.

Il Falconiere - Relais e Chateaux

Cortona

10/10 Exceptional

This was the first hotel we visited in our two week Tuscany vacation. Coming out of Rome and getting on the highway north, it looked like the exit should be labeled for Cortona...but it wasn't and we wasted a lot of time getting lost (our fault). Once we found the hotel, it was a gem in the hills in the vineyards. Breakfast on the patio of the little glass Liminoere building was fabulous. Loved their boxer dog roamed around saying "hi". Owner/chef is on premises and she gives cooking lessons....

Barbara

A dining table with two wine glasses, a candle, and a bottle of champagne, overlooking a swimming pool and a tree.

A garden pathway leading to a rustic house with a tiled roof, surrounded by various plants and a clear sky.

A large estate with a swimming pool, vineyard, and multiple buildings.

A rustic dining area with wooden tables and chairs, a stone floor, and a view of a vineyard through large windows.

Agriturismo Merigge Wellness & Spa

Montepulciano

10/10 Exceptional

Francisco

A pool with a view of a green landscape and trees.

A dining area with tables set for a meal, featuring white tablecloths, clear glassware, and floral centerpieces.

A rustic stone building with a cozy interior, surrounded by lush greenery and flowering plants.

A rustic outdoor dining area with stone walls, a wooden table, metal chairs, and two lit lanterns.

Villa Cicolina

Montepulciano

10/10 Exceptional

This was a very special place for my husband and me. We felt relaxed and pampered in a perfect Italian countryside environment. A friend recommended it to me and she was spot on! The grounds were beautiful, the rooms were special, and the separate dining room made you feel like you were in the heart of Tuscany....because you are! You are 2 miles from downtown Montelpulciano, 40 min from Montalcino, 40 from Sienna, and close to the most wonderful vineyards. We ate and drank our way through...

Nanette

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

A pathway flanked by lush greenery and palm trees, leading to a building with large glass windows.

A building facade with multiple storefronts, including a visible shop with a sign that reads "I SMELL SUGAR ONLY T-SHIRT."

SUGAR ROOMS Residenza d' Epoca

Arezzo Centro Storico

10/10 Exceptional

Stout

A cozy room with a fireplace, two armchairs, and a table.

A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.

A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

Tenuta Santo Pietro

Pienza

10/10 Exceptional

C N

Villa Borgo San Pietro

Cortona

10/10 Exceptional

This was the best hotel experience of our lives! This is a beautiful old Italian farmhouse that has been completely remodeled but preserves all of the charm. A bit difficult to find, but worth it. The staff was the best staff we have ever seen in a hotel, and we travel a lot. We stayed 5 nights and got to feel we were friends with all of them. They treated us like family and were ever ready to assist if we needed it, i.e., helping us map out our week of activities, recommending restaurants,...

Anonymous traveler