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

Hotels with a Pool in Cortona

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Hotels with a Pool in Cortona

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

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

A balcony with a pool view, a small table, and a chair.

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

1. Monastero di Cortona Hotel & Spa

Cortona Old Town

Indoor pool
Hot tub

$251

$285 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.

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

2. Relais Villa Baldelli

Cortona

Poolside bar
Pool loungers

$128

$150 total

includes taxes & fees

Sep 28 - Sep 29

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

A person in a white robe standing by a window with a view of mountains.

A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

A couple dining at a table with a scenic view of mountains and a lake.

3. Locanda agli Amici

Cortona

Pool loungers

$100

$119 total

includes taxes & fees

Oct 25 - Oct 26

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

A stone building with multiple windows and a courtyard.

A stone building with outdoor seating and a fountain.

4. Villa Borgo San Pietro

Cortona

Pool loungers

$117

$137 total

includes taxes & fees

Oct 5 - Oct 6

A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.

A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.

A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.

A cozy living room with a fireplace, a sofa, a dining table, and various decorative items.

5. Locanda del Molino

Cortona

Outdoor pool
Poolside bar
Pool loungers

$78

$95 total

includes taxes & fees

Oct 27 - Oct 28

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

A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.

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

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

6. Cortona Resort - Le Terre Dei Cavalieri

Cortona

Outdoor pool
Poolside bar
Pool loungers

$132

$151 total

includes taxes & fees

Sep 28 - Sep 29

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

A balcony with a table and chairs, a potted plant, and a view of a green landscape.

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

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

7. Il Falconiere - Relais e Chateaux

Cortona

2 outdoor pools
Poolside bar
Pool loungers
Hot tub

$424

$475 total

includes taxes & fees

Oct 27 - Oct 28

A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.

A round table set for dining with candles, wine glasses, and a bottle of wine. A stone wall and wooden furniture are in the background.

A spacious hallway with wooden flooring, a wooden cabinet with a mirror, and two candle lanterns.

A bedroom with a bed, a chair, a table with a candle, and a wardrobe.

8. Cortona Resort Spa

Cortona

Outdoor pool
Hot tub

$150

$168 total

includes taxes & fees

Oct 5 - Oct 6

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

A well-maintained garden with a wooden pergola, stone structures, and lush greenery.

A kitchen with stone walls, a gas stove, and a wooden shelf with wine bottles.

A stone staircase leading to a wooden porch with potted plants.

9. Country House Podere Casorbica

Cortona

Pool loungers

$65

$86 total

includes taxes & fees

Oct 4 - Oct 5

A large, rectangular swimming pool surrounded by a well-maintained lawn, with a house and garden in the background.

A well-maintained lawn with a brick house and a flag, surrounded by trees and a clear sky.

A house with a tiled roof, surrounded by a well-maintained garden and trees.

A traditional villa with a garden, outdoor seating, and a clear blue sky.

10. Casa Bellavista

Cortona

Pool loungers
Hot tub

$197

$221 total

includes taxes & fees

Oct 18 - Oct 19

A rectangular swimming pool with clear blue water, surrounded by a paved deck and a gazebo.

A bedroom with a wooden ceiling, a chandelier, a bed, a dresser, and a chair.

A formal dining room with a large table, chairs, and a chandelier.

An outdoor dining table set with tea, coffee, and pastries, surrounded by white metal chairs and a stone fountain in the background.

11. Agriturismo Villa Augusto

Cortona

Pool loungers

$166

$188 total

includes taxes & fees

Oct 3 - Oct 4

A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.

A spacious bathroom with a large wooden bathtub, a freestanding mirror, and a glass-enclosed shower.

A long banquet table with gold candelabras, white flowers, and gold tableware.

A historic stone building with arched doorways and a courtyard at twilight.

12. Relais La Corte dei Papi

Cortona

Outdoor pool
Poolside bar
Pool loungers
Full-service spa

$353

$398 total

includes taxes & fees

Oct 26 - Oct 27

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.

An outdoor dining area with tables set for a meal, surrounded by greenery and trees.

A buffet with various food items, a vase of flowers, and a mirror reflecting the room.

A hallway with a checkered floor, arched windows, and a chandelier.

13. Villa di Piazzano - Small Luxury Hotel of the World

Cortona

Outdoor pool
Poolside bar
Pool loungers

$643

$716 total

includes taxes & fees

Oct 14 - Oct 15

14. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

Indoor pool
Pool loungers
Hot tub

$110

$168 total

includes taxes & fees

Sep 28 - Sep 29

A rectangular swimming pool with a tiled deck, surrounded by lounge chairs and umbrellas.

A traditional room with a fireplace, wooden furniture, and a large mirror.

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

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

15. Podere La Rocca

Montepulciano

Outdoor pool
Pool loungers
Hot tub

$158

$178 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A playground with a slide and swings, surrounded by lush greenery and flowering plants.

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

16. Borgo Tre Rose

Montepulciano

Outdoor pool
Pool loungers

$74

$86 total

includes taxes & fees

Oct 24 - Oct 25

A hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.

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

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.

17. Hotel Park

Castiglion Fiorentino

Pool loungers

$107

$122 total

includes taxes & fees

Sep 29 - Sep 30

A nighttime swimming pool area with lounge chairs and umbrellas, surrounded by stone buildings and trees.

A bedroom with a large window and a view of a cityscape.

Villa Paradiso with a stone wall entrance, a metal gate, and a signboard.

A spacious room with stone walls, wooden beams, and tiled flooring. There are several chairs and a table, along with potted plants.

18. Hotel Villa Paradiso

Passignano sul Trasimeno

Outdoor pool
Pool loungers
Near the beach

$63

$74 total

includes taxes & fees

Oct 11 - Oct 12

A landscaped garden with a swimming pool, neatly trimmed hedges, and outdoor seating areas.

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

A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

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

19. La Cantina Relais - Fattoria Il Cipresso

Arezzo

Outdoor pool
Pool loungers

$101

$117 total

includes taxes & fees

Oct 12 - Oct 13

A waterfront hotel with a swimming pool, a boat dock, and a view of the water.

A waterfront hotel with multiple balconies, a calm river, and a dock with boats.

A marina with boats docked, a waterfront building, and a cityscape in the background.

A waterfront restaurant with outdoor seating, a view of a river, and buildings in the background.

20. Hotel Lidò

Passignano sul Trasimeno

Outdoor pool
Pool loungers
Near the beach
Hot tub

$103

$117 total

includes taxes & fees

Oct 2 - Oct 3

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Discover your perfect hotel with a pool in Cortona

Breakfast included

4 stars

5 stars

Spa

Hot tub

Hotels with pools and free breakfast in Cortona

A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.

Monastero di Cortona Hotel & Spa

Cortona Old Town

$251

$285 total

includes taxes & fees

Oct 25 - Oct 26

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

A stone building with a red awning, potted plants, and a staircase leading to the entrance.

Il Falconiere - Relais e Chateaux

Cortona

$424

$475 total

includes taxes & fees

Oct 27 - Oct 28

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

Relais Villa Baldelli

Cortona

$128

$150 total

includes taxes & fees

Sep 28 - Sep 29

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

Villa Borgo San Pietro

Cortona

$117

$137 total

includes taxes & fees

Oct 5 - Oct 6

Locanda agli Amici

Cortona

$100

$119 total

includes taxes & fees

Oct 25 - Oct 26

Two people seated at a round table outdoors, with a candle and food on the table, and a large tree in the background.

A two-story building with a stone staircase leading to a door, a scooter parked in front, and a garden with potted plants.

Cortona Resort Spa

Cortona

$150

$168 total

includes taxes & fees

Oct 5 - Oct 6

Villa di Piazzano - Small Luxury Hotel of the World

Cortona

$643

$716 total

includes taxes & fees

Oct 14 - Oct 15

A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.

A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.

Relais La Corte dei Papi

Cortona

$353

$398 total

includes taxes & fees

Oct 26 - Oct 27

A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.

Locanda del Molino

Cortona

$78

$95 total

includes taxes & fees

Oct 27 - Oct 28

Cortona Resort - Le Terre Dei Cavalieri

Cortona

$132

$151 total

includes taxes & fees

Sep 28 - Sep 29

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Top neighborhoods in Cortona

Cortona Old Town

A historic town with medieval architecture, including a prominent tower and a church with a bell tower.

A historic European town square with stone buildings, green shutters, and outdoor seating areas.

A street with a shop selling jewelry and a signboard.

A historic stone building with a bell tower, surrounded by lush greenery and olive trees.

Cortona Old Town

The Cortona Old Town neighborhood has lots to see including Piazza della Repubblica and Museum of the Etruscan Academy.

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Top landmarks in Cortona

Villa Bramasole

9.2/10 (20 reviews)

If you're planning a bit of sightseeing during your trip, head to Villa Bramasole— just one of the landmarks located 0.6 mi (1 km) from central Cortona.

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Piazza della Repubblica

9.4/10 (95 reviews)

Piazza della Repubblica is worth passing through for a few pics when in Cortona Old Town.

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Cortona Cathedral

9.4/10 (77 reviews)

Cortona Old Town is home to Cortona Cathedral, so why not stop by during your stay in Cortona.

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Fortress of Girifalco

8.8/10 (25 reviews)

If you're planning a bit of sightseeing head to Fortress of Girifalco— just one of the monuments in Cortona Old Town.

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Santa Margherita Basilica

9.2/10 (30 reviews)

If you're interested in local churches head to Cortona Old Town— home to Santa Margherita Basilica.

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Santa Maria Nuova

8.8/10 (5 reviews)

If you're planning a bit of sightseeing during your trip, head to Santa Maria Nuova— just one of the landmarks located 0.4 mi (0.6 km) from central Cortona.

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Museum of the Etruscan Academy

8.8/10 (18 reviews)

Museum of the Etruscan Academy is just one of the attractions in Cortona Old Town, Cortona so you might want to stop by during your trip. If you want to experience more of the culture Cortona has to offer, head to Piazza della Repubblica, Cortona Cathedral, and Santa Maria Nuova.

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Palazzo Comunale

9.2/10 (44 reviews)

Palazzo Comunale is worth a pic or two when discovering Cortona Old Town.

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About the destination

If you're looking to discover somewhere new, look no further than Cortona. Whether you're planning to stay for a night or for the week, the area around Cortona has accommodations to fit every need. Search for hotels in Cortona with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Cortona hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Cortona hotel deals are here with our lowest price guarantee.