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Casamaggiore Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Casamaggiore vacation rentals

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

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

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"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...
United Kingdom
Anna
The price is CA $116
CA $151 total
includes taxes & fees
Nov 22 - Nov 23
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
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

Casa di Cristina - Castiglione del lago
Casamaggiore
The price is CA $142
CA $142 total
includes taxes & fees
Nov 9 - Nov 10
Casa di Cristina - Castiglione del lago
Terrace/patio

3. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is CA $168
CA $191 total
includes taxes & fees
Nov 15 - Nov 16
Casale dell'Assiolo
A dining area with a wooden table, chairs, and a potted plant.

4. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is CA $167
CA $187 total
includes taxes & fees
Nov 7 - Nov 8
La Piccola Locanda
A patio area with outdoor seating, potted plants, and a view of the landscape.

5. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is CA $145
CA $198 total
includes taxes & fees
Nov 9 - Nov 10
Affitacamere Maria Gabriella
A terrace with a table set for breakfast, overlooking a scenic landscape.

6. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $241
CA $271 total
includes taxes & fees
Nov 7 - Nov 8
Delcorto Suites
A large building with a cafe area, outdoor seating, and a covered patio.

7. La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.0 out of 10, Wonderful, (9 reviews)
"It was such a lovely experience. Bang in the centre of the town, still very quiet. The room was breathtaking, lovely breakfast (generosity though depended on staff). Overall such a great experience I would go back today!"
United Kingdom
GianPaolo
The price is CA $177
CA $195 total
includes taxes & fees
Dec 2 - Dec 3
La Locanda Di Cetona
A balcony with a view of a historic town, featuring terracotta-roofed buildings and a prominent church tower.

8. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is CA $199
CA $225 total
includes taxes & fees
Nov 17 - Nov 18
Meublé Il Riccio
A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

9. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is CA $211
CA $239 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

10. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is CA $91
CA $105 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais
A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a lamp, and a window with sheer curtains.

11. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is CA $136
CA $156 total
includes taxes & fees
Nov 8 - Nov 9
Bed & Breakfast Vicolo dell'Oste
Exterior

12. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is CA $168
CA $191 total
includes taxes & fees
Nov 8 - Nov 9
montorio
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

13. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (170 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is CA $192
CA $221 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
An arched doorway leading to a building with a wooden door and a staircase.

14. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is CA $126
CA $145 total
includes taxes & fees
Nov 11 - Nov 12
Residenza Fabroni
A view through a glass door into a patio area with a white chair, a table, and a banner advertising a boutique hotel.

15. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is CA $119
CA $145 total
includes taxes & fees
Nov 8 - Nov 9
Boutique Apartment Eleganza
A bedroom with a bed, a TV, a wardrobe, and a view of a garden.

16. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is CA $111
CA $136 total
includes taxes & fees
Nov 9 - Nov 10
Boutique Apartment Natura
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

17. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $109
CA $127 total
includes taxes & fees
Nov 7 - Nov 8
Artisti del Cavallo Tourism
A window with a view of a green landscape and hills.

18. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (140 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is CA $324
CA $362 total
includes taxes & fees
Nov 10 - Nov 11
Il Tosco
A deck with wicker furniture, a flag, and a view of a lake.

19. Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Panicale
The price is CA $240
CA $316 total
includes taxes & fees
Nov 7 - Nov 8
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

20. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
B&B Piccolo Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Casamaggiore Hotel Reviews

Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"Great place to stay. Perfect location. Wonderful breakfast. Nice room. Underground parking could be a bit nicer, but they are actively working on it. Great place."
JOHN PAUL 2-night trip
Posted 3 days ago
Hotel San Gregorio

Find out more about Casamaggiore

Everything you need to know about Casamaggiore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Casamaggiore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Casamaggiore vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Casamaggiore vacation rentals we have selected for you start as low as CA $105 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 vacation 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 vacation.

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 vacation rentals in Casamaggiore?

Yes, we give you a choice of vacation rentals close to top local attractions in Casamaggiore, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Casamaggiore?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: Visitors like this Casamaggiore vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Casamaggiore?

With 3 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Casamaggiore like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Casamaggiore. Vacation rentals offer extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for families.