La Strada-Santa Cristina Holiday Rentals, Castiglion Fiorentino: Private House Rentals

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Go beyond your typical stay in La Strada-Santa Cristina

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Villa

Pool

Condo

Hot tub

Spa

Family friendly

Farm

Waterpark

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Our top choices for La Strada-Santa Cristina hotels

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

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

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.

1. Relais Villa Baldelli

Cortona

Peter

Rp2.303.238

Rp2.697.109 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

2. Il Falconiere - Relais e Chateaux

Cortona

Qingwen

Rp7.301.111

Rp8.194.770 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with outdoor seating and a fountain.

A stone building with multiple windows and a courtyard.

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

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

3. Villa Borgo San Pietro

Cortona

Olga

Rp2.084.810

Rp2.456.435 total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with two beds, a desk, a chair, and a phone on a bedside table.

4. HOTEL PLANET INTERNATIONAL

Arezzo

Naji

Rp1.309.650

Rp1.563.276 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A narrow hallway with a stone wall and a clock.

5. Monastero di Cortona Hotel & Spa

Cortona Old Town

Alexander

Rp4.497.819

Rp5.111.149 total

includes taxes & fees

25 Oct - 26 Oct

A couple in a hot tub with a cityscape view through large windows.

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

A bathroom with a bathtub, a table with a vase of flowers, and a view of the countryside through a window.

A balcony with terracotta pots of flowers, a view of a rural landscape, and a stone building with a tiled roof.

6. Hotel San Michele

Cortona Old Town

Tala

Rp2.766.310

Rp3.206.489 total

includes taxes & fees

8 Oct - 9 Oct

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 reception area with a wooden console table, two wall clocks, and a staircase leading to an upper level.

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

7. Hotel San Luca

Cortona Old Town

Mariusz

Rp1.452.449

Rp1.761.242 total

includes taxes & fees

25 Oct - 26 Oct

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.

8. Cortona Resort - Le Terre Dei Cavalieri

Cortona

Dana

Rp2.413.420

Rp2.756.979 total

includes taxes & fees

30 Sept - 1 Oct

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

A historic stone building with a sign reading "Hotel Italia."

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.

9. Hotel Italia

Cortona Old Town

Frances

Rp2.178.816

Rp2.498.915 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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

10. Hotel Park

Castiglion Fiorentino

Karen

Rp1.918.795

Rp2.192.246 total

includes taxes & fees

7 Oct - 8 Oct

A stone building with a courtyard, outdoor seating, and a view of the landscape.

A dining table set for two with a view of a sunset over a landscape.

A stone building with a pool and outdoor seating area, surrounded by trees and a view of the countryside.

A garden with a stone pathway, a wooden barrel, and a view of the countryside.

11. Villa Schiatti

Castiglion Fiorentino

Soudabeh

Rp2.828.449

Rp3.193.068 total

includes taxes & fees

30 Sept - 1 Oct

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.

12. La Cantina Relais - Fattoria Il Cipresso

Arezzo

Ronald

Rp1.800.423

Rp2.102.824 total

includes taxes & fees

12 Oct - 13 Oct

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

An outdoor dining area with tables and chairs, a garden with a lawn and potted plants, and a building with multiple windows and balconies.

13. Hotel Villa Marsili

Cortona Old Town

fares

Rp3.612.921

Rp4.137.762 total

includes taxes & fees

10 Oct - 11 Oct

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

A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.

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

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

14. Villa Santa Margherita

Cortona Old Town

George F

Rp2.085.646

Rp2.396.176 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

15. Cortona Resort Spa

Cortona

Candice

Rp2.752.538

Rp3.089.122 total

includes taxes & fees

30 Sept - 1 Oct

An outdoor event with people seated at tables, surrounded by stone buildings and greenery.

A modern interior with a stone wall, a wooden bench, and a glass door leading to a dark room.

A couple in a bathtub with candles, suggesting a romantic setting.

A stone building with a grassy courtyard, a staircase, and a small garden area.

16. San Michele al Castello

Castiglion Fiorentino

Alejandro

Rp2.065.721

Rp2.354.067 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

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

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

Cortona

Rushab

Rp11.535.440

Rp12.852.614 total

includes taxes & fees

14 Oct - 15 Oct

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

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

A bedside table with a vase of flowers, a book, and a drawer.

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.

18. Locanda agli Amici

Cortona

David

Rp1.787.216

Rp2.129.081 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

19. Hotel Le Capanne

Arezzo

Robert

Rp2.091.300

Rp2.422.890 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

20. Relais La Corte dei Papi

Cortona

Frithjof

Rp6.338.813

Rp7.136.242 total

includes taxes & fees

26 Oct - 27 Oct

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Stay near popular La Strada-Santa Cristina attractions

Agricola Buccelletti Winery

10.0/10 (2 reviews)

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

See properties

Top La Strada-Santa Cristina Hotel Reviews

Villa Tiberini Wine Relais

10/10 Excellent

"It's great place for the large family."

Agriturismo Borgo Sette Tigli

10/10 Excellent

"The room was as advertised. Clean one bedroom apartment. If you stay here there are several room options. Ours didn't have a best view or patio (number 7) so maybe there is a way to request that. The pool was nice and relaxing to be at during the hot afternoons. The property was very quiet. We could sleep with the windows open. The access to the stay is by a dirt road, but you don't need Four wheel drive. Any car will work. The location was great as we were close to small towns for traveling. We needed a crib and that was set up for us on arrival. A highchair was also provided. The hosts were responsive with any issues brought up. I would stay here again."

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!"

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Amazing stay for our 25th anniversary. The property is breathtaking and every corner was like a Tuscan postcard! The room was beautiful, the pools were great and the food was exceptional. Would highly recommend and would go back in a second!"

Borgo San Vincenzo

10/10 Excellent

"It is a very nice property right next to a vineyard. 10-15 minutes drive to Montepulciano. Not for those who don’t have cars, my guess. Staff was excellent. Owners are very helpful."

Hotel Minerva

10/10 Excellent

"Eccellente"

Hotel Garden Experience

10/10 Excellent

"Tout est super je le recomendé fortement"

More cheap stays in La Strada-Santa Cristina

Hotel Chenno

Via Don Lorenzo Boschi 29 Subbiano AR

Rp834.277

Rp978.863 total

9 Oct - 10 Oct

includes taxes & fees

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

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Tenuta La Pieve Casale La Valle

Via Giovanni XXII Pergine Valdarno AR

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Tenuta La Pieve Casale Il Giglio

Via Della Ghiacciaia Pergine Valdarno AR

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Residence Peloni

Via Polidori 50 Arezzo AR

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Belvedere

Via dei Mandorli 17 Passignano sul Trasimeno PG

Get rates

7.6/10 Good! (16 reviews)

Frequently asked questions

Where is the best place for a stay in La Strada-Santa Cristina?

Located 7.9 mi (12.6 km) from the heart of La Strada-Santa Cristina, Villa di Piazzano - Small Luxury Hotel of the World is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are Monastero di Cortona Hotel & Spa and Hotel Continentale. See all available top hotels, or vacation rentals in La Strada-Santa Cristina.

If I need to cancel my hotel reservation in La Strada-Santa Cristina, will I receive a refund?

Yes, most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in La Strada-Santa Cristina.

What are some hotels with pools in La Strada-Santa Cristina?

Villa di Piazzano - Small Luxury Hotel of the World: Offers a snack bar/deli, an outdoor pool and free self parking. Monastero di Cortona Hotel & Spa and Villa Tiberini Wine Relais are a couple of other choices that feature an on-site pool. View all hotels with pools in La Strada-Santa Cristina.

What is staying in La Strada-Santa Cristina like?

Visitors can enjoy all that La Strada-Santa Cristina has to offer, including its wineries. In La Strada-Santa Cristina, there are 10 hotels and other accommodation options to choose from. Find out more about La Strada-Santa Cristina.

What is there to see in La Strada-Santa Cristina?

A favourite place to visit is Agricola Buccelletti Winery. You'll also find Tennis Club Castiglionese and Fortress of Girifalco in the area. Take a look at what more there is to see and do in Expedia's La Strada-Santa Cristina guide.

What's the weather like in La Strada-Santa Cristina?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for La Strada-Santa Cristina is 906 mm.

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Find hotels in La Strada-Santa Cristina from Rp978.863

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in La Strada-Santa Cristina

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for La Strada-Santa Cristina hotels

1. Relais Villa Baldelli

2. Il Falconiere - Relais e Chateaux

3. Villa Borgo San Pietro

4. HOTEL PLANET INTERNATIONAL

5. Monastero di Cortona Hotel & Spa

6. Hotel San Michele

7. Hotel San Luca

8. Cortona Resort - Le Terre Dei Cavalieri

9. Hotel Italia

10. Hotel Park

11. Villa Schiatti

12. La Cantina Relais - Fattoria Il Cipresso

13. Hotel Villa Marsili

14. Villa Santa Margherita

15. Cortona Resort Spa

16. San Michele al Castello

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

18. Locanda agli Amici

19. Hotel Le Capanne

20. Relais La Corte dei Papi

Stay near popular La Strada-Santa Cristina attractions

Agricola Buccelletti Winery

Top La Strada-Santa Cristina Hotel Reviews

Villa Tiberini Wine Relais

Agriturismo Borgo Sette Tigli

Hotel San Michele

Villa di Piazzano - Small Luxury Hotel of the World

Il Falconiere - Relais e Chateaux

Borgo San Vincenzo

Hotel Minerva

Hotel Garden Experience

More cheap stays in La Strada-Santa Cristina

Hotel Chenno

Tenuta La Pieve Casale Presciano

Tenuta La Pieve Casale La Valle

Tenuta La Pieve Casale Il Giglio

Residence Peloni

Belvedere

Frequently asked questions

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