Search Holiday Rentals in Casamaggiore

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November 2026

December 2026

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Our top choices for Casamaggiore holiday rentals

A rustic brick building with a mural, a clock, and various potted plants.

1. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casamaggiore

"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...

Anna

includes taxes & fees

11 Nov - 12 Nov

A cozy outdoor seating area with a wooden chair and table, surrounded by potted plants and a rustic wooden wall.

2. Casa di Cristina - Castiglione del lago

Casamaggiore

includes taxes & fees

11 Nov - 12 Nov

3. Casale dell'Assiolo

Castiglione del Lago

Emma

includes taxes & fees

14 Nov - 15 Nov

A dining area with a wooden table, chairs, and a potted plant.

4. La Piccola Locanda

Chiusi

autumn

includes taxes & fees

11 Nov - 12 Nov

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

5. Abbadia Sicille Relais

Trequanda

Robert

includes taxes & fees

10 Dec - 11 Dec

A large building with a cafe area, outdoor seating, and a covered patio.

6. La Locanda Di Cetona

Cetona

GianPaolo

includes taxes & fees

8 Dec - 9 Dec

A patio area with outdoor seating, potted plants, and a view of the landscape.

7. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

includes taxes & fees

17 Nov - 18 Nov

A view through a glass door into a patio area with a white chair, a table, and a banner advertising a boutique hotel.

8. Boutique Apartment Eleganza

Chiusi Scalo

Ryan W.

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a bed, a TV, a wardrobe, and a view of a garden.

9. Boutique Apartment Natura

Chiusi

Shelley

includes taxes & fees

16 Nov - 17 Nov

A pool area with a rectangular pool, sun loungers, and a wooden play structure.

10. Poggiovalle Tenuta Italiana

Città della Pieve

Carlotta

includes taxes & fees

4 Dec - 5 Dec

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

11. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

17 Nov - 18 Nov

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a lamp, and a window with sheer curtains.

12. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Melissa

includes taxes & fees

12 Nov - 13 Nov

A park with picnic tables, a playground, and a gravel path.

13. Vacation home with a panoramic terrace, ideal for families and couples

Cortona

includes taxes & fees

12 Nov - 13 Nov

A rustic dining area with a wooden table, chairs, and a stone wall in the background.

14. Le Coin des Murs—Panicale Historic Center

Panicale

includes taxes & fees

12 Nov - 13 Nov

A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

15. La Locanda di San Francesco

Montepulciano

Colin

includes taxes & fees

26 Nov - 27 Nov

An arched doorway leading to a building with a wooden door and a staircase.

16. Residenza Fabroni

Montepulciano

Marc

includes taxes & fees

12 Nov - 13 Nov

A stone building with a tiled roof, surrounded by tall trees and a gravel path.

17. montorio

Montepulciano

Joseph

includes taxes & fees

12 Nov - 13 Nov

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

18. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

Toscana

includes taxes & fees

16 Nov - 17 Nov

A balcony with a view of a historic town, featuring terracotta-roofed buildings and a prominent church tower.

19. Meublé Il Riccio

Montepulciano

Slimane

includes taxes & fees

12 Nov - 13 Nov

A cozy living room with a sofa, wicker chairs, a wooden coffee table, and a kitchen in the background.

20. 2 King Bed, 2 Full Bathroom Apartment in Città della Pieve, Umbria - Tuscany

Città della Pieve

Waseemuddin S.

includes taxes & fees

13 Nov - 14 Nov

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Find holiday rentals that suit your style

Top Casamaggiore Hotel Reviews

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casamaggiore

10/10 Excellent

Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...

Anna

A garden pathway leading to a building with a yellow facade and arched windows.

Residenza Dei Ricci Relais

Chiusi

10/10 Excellent

Ann Marie

A historic building with a courtyard, surrounded by lush greenery and trees.

Equo Suites

Castiglione del Lago

10/10 Excellent

Louise

A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

Relais Villa Grazianella - UNA Esperienze

Montepulciano

10/10 Excellent

Sandeep

A pool with lounge chairs, surrounded by trees and a hilly landscape.

Hotel Villa il Patriarca

Chiusi

10/10 Excellent

Renato

An arched entrance with a wooden balcony, a tiled floor, and a door leading inside.

Hotel Boutique Castiglione del Lago

Contrada Castello

10/10 Excellent

Jane

Terra Antica Resort

Montepulciano

10/10 Excellent

We were travelling as a family of four. We had booked the Montepulciano 2 bedroom suite, but were delighted to be told on arrival that we'd been upgraded to the best villa on resort(!), Villa Nobile. This included a private pool and hot tub, all with fantastic views across the Tuscan countryside. The accommodation was v high standard and extremely luxurious. The service was fantastic, especially Natalia on arrival. If you're visiting on a Friday, then recommend joining the bbq...great food and...

Lewis

A spacious dining area with a long wooden table, multiple chairs, and hanging wicker lamps.

Agriturismo Antica Corte

Montepulciano

10/10 Excellent

Farah

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

Agriturismo Merigge Wellness & Spa

Montepulciano

10/10 Excellent

Thomas

A hotel entrance with a sign reading "ALBERGO" and various potted plants and flowers.

La Torre

Contrada Castello

10/10 Excellent

Great little hotle in the heart of town, the owners are exceptionally friendly and helpful. The hotel is ideally suited for exploring Tuscany and Umbria. Close to Perugia, Cortona and Pienza as well as other delightful Italian hilltop villages. The hotel is located in the centre of Castiglion del Lago,which overlooks Lake Tresimino. The views from the town are stunning. Hotel highly recommended. Close to lots of restaurants.

Sandra

A terrace with two sun loungers, a metal railing, and a view of a town with buildings and trees.

Santa Caterina Hotel & Bike

Chianciano Terme

10/10 Excellent

Sor Eng

A brick building with a sign reading "SVETONI Wine Resort" at its entrance.

Villa Svetoni Wine Resort

Montepulciano

10/10 Excellent

Katie

A wooden interior with a bench and a window overlooking a garden.

The Monteleone

Monteleone d'Orvieto

10/10 Excellent

Flawless stay, absolutely stunning hotel and grounds, matched by wonderful attention from every member of the team who made our stay completely memorable. Room exceeded our expectations- spacious, cool and very comfortable, beautifully designed with gorgeous bed. We loved the breakfast options- hot and cold choices, including many homemade options which were delicious. The pool was clean and a perfect temperature, surrounded by nature- it was a perfect environment for us to relax and soak up...

Joanna

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

Podere La Rocca

Montepulciano

10/10 Excellent

Giovanni

Find out more about Casamaggiore

Everything you need to know about Casamaggiore holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Casamaggiore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Casamaggiore holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Casamaggiore holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Casamaggiore. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Casamaggiore holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Casamaggiore holiday rentals we have selected for you start as low as £53 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Casamaggiore rentals

At Expedia, we put the best Casamaggiore holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Casamaggiore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Casamaggiore holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Casamaggiore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Casamaggiore?

Yes, there are holiday rentals close to the most popular sights in Casamaggiore, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Casamaggiore has to offer?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This holiday home rental outside of Casamaggiore is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Casamaggiore?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Casamaggiore stay.

What’s there to see and do in Casamaggiore?

Explore the area and family-friendly sights such as Tavernelle Aquatic Park, or get out into nature at a spot like Chiusi Lake. Lake Trasimeno and Val di Chiana are a couple of places you'll find in the wider area.

What’s a holiday rental in Casamaggiore like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Casamaggiore. Holiday rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.

Search Holiday Rentals in Casamaggiore

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Casamaggiore holiday rentals

1. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

2. Casa di Cristina - Castiglione del lago

3. Casale dell'Assiolo

4. La Piccola Locanda

5. Abbadia Sicille Relais

6. La Locanda Di Cetona

7. Affitacamere Maria Gabriella

8. Boutique Apartment Eleganza

9. Boutique Apartment Natura

10. Poggiovalle Tenuta Italiana

11. Artisti del Cavallo Tourism

12. Bed & Breakfast Vicolo dell'Oste

13. Vacation home with a panoramic terrace, ideal for families and couples

14. Le Coin des Murs—Panicale Historic Center

15. La Locanda di San Francesco

16. Residenza Fabroni

17. montorio

18. Double room with private bathroom in the countryside, 5 minutes from Montepulciano

19. Meublé Il Riccio

20. 2 King Bed, 2 Full Bathroom Apartment in Città della Pieve, Umbria - Tuscany

Find holiday rentals that suit your style

Top Casamaggiore Hotel Reviews

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

10/10 Excellent

Find out more about Casamaggiore

Casamaggiore holiday rentals: An excellent choice for every season

How to find incredible deals on Casamaggiore rentals

Frequently Asked Questions

Can I find holiday rentals in Casamaggiore?

What are some of the best holiday rentals that Casamaggiore has to offer?

How many holiday rentals will I find in Casamaggiore?

What’s there to see and do in Casamaggiore?

What’s a holiday rental in Casamaggiore like?