A hillside town with historic buildings and a prominent church.

Citta della Pieve Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Citta della Pieve vacation rentals

A bakery display with various pastries and desserts.

1. 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
$111 nightly
The price is $124
Oct 3 - Oct 4
Total with taxes and fees
La Piccola Locanda
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

2. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
$142 nightly
The price is $159
Oct 2 - Oct 3
Total with taxes and fees
Borgo Dolciano
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

3. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (17 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
$83 nightly
The price is $93
Oct 7 - Oct 8
Total with taxes and fees
FonteLiving
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (158 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
$144 nightly
The price is $165
Oct 28 - Oct 29
Total with taxes and fees
Hotel San Gregorio
An open door leading to a balcony with wicker furniture and a view of a historic tower.

5. Affittacamere Valentina

Affittacamere Valentina
Orvieto
9.4 out of 10, Exceptional, (203 reviews)
"Evrething is good, clean room, staff and location."
United States
Laura
$113 nightly
The price is $129
Oct 26 - Oct 27
Total with taxes and fees
Affittacamere Valentina
A terrace with a table set for breakfast, overlooking a scenic landscape.

6. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (46 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
$188 nightly
The price is $211
Oct 6 - Oct 7
Total with taxes and fees
Delcorto Suites
A crowded restaurant with brick walls and multiple tables and chairs.

7. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (149 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
$208 nightly
The price is $233
Oct 12 - Oct 13
Total with taxes and fees
La Locanda di San Francesco
An interior courtyard with stone columns, arches, and a mosaic.

8. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 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
$150 nightly
The price is $170
Oct 12 - Oct 13
Total with taxes and fees
Meublé Il Riccio
Front of property

9. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
$114 nightly
The price is $130
Oct 5 - Oct 6
Total with taxes and fees
montorio
An arched doorway leading to a building with a wooden door and a staircase.

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (111 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
$80 nightly
The price is $93
Oct 23 - Oct 24
Total with taxes and fees
Residenza Fabroni
A patio with stone flooring, outdoor furniture, and a view of the countryside.

11. Misia Country Resort

Misia Country Resort
Orvieto
9.4 out of 10, Exceptional, (154 reviews)
"really nice setting, very nice rooms and breakfast"
Canada
Jean
$164 nightly
The price is $185
Oct 18 - Oct 19
Total with taxes and fees
Misia Country Resort
A patio area with outdoor seating, potted plants, and a view of the landscape.

12. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (68 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$118 nightly
The price is $135
Oct 7 - Oct 8
Total with taxes and fees
Affitacamere Maria Gabriella
A poolside area with two glasses of water, candles, and a stone pathway.

13. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (97 reviews)
"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."
Canada
Zoltan
$169 nightly
The price is $191
Oct 30 - Oct 31
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

14. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
$107 nightly
The price is $122
Nov 1 - Nov 2
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
A historic building with a tower, a courtyard, and a well-lit entrance.

15. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
$123 nightly
The price is $138
Oct 28 - Oct 29
Total with taxes and fees
Abbadia Sicille Relais
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

16. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
$327 nightly
The price is $364
Oct 5 - Oct 6
Total with taxes and fees
Il Tosco
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

17. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
$499 nightly
The price is $553
Oct 30 - Oct 31
Total with taxes and fees
L'Olmo
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

18. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
$87 nightly
The price is $100
Nov 1 - Nov 2
Total with taxes and fees
TuscanyLettings Studio&Room
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

19. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
$143 nightly
The price is $162
Nov 1 - Nov 2
Total with taxes and fees
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A modern bathroom with a freestanding bathtub, a wooden robe rack, and a large mirror.

20. Welchome suites

Welchome suites
Old Town Perugia
9.4 out of 10, Exceptional, (33 reviews)
"Clean, great staff and assistance when needed. Very comfortable and would stay again"
Canada
Adam
$143 nightly
The price is $160
Oct 4 - Oct 5
Total with taxes and fees
Welchome suites
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 Citta della Pieve Hotel Reviews

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"All good"
Leo 4-night trip
Posted 21 hours ago
Hotel San Gregorio

Find out more about Citta della Pieve

Everything you need to know about Citta della Pieve 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 Citta della Pieve vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Citta della Pieve vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Citta della Pieve vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Citta della Pieve. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Citta della Pieve in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Citta della Pieve rentals

At Expedia, we put the best Citta della Pieve 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 Citta della Pieve 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 Citta della Pieve 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 Citta della Pieve. 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 Citta della Pieve?

Yes, we have vacation rentals in Citta della Pieve near Centro Servizi Turistici Citta della Pieve, or you can go with a more remote option if you're looking for extra privacy while you relax. Citta della Pieve is known for its cathedral and musical theater. Make sure you have time to check out the art and local tours during your trip.

What are some of the best vacation home rentals in Citta della Pieve?

Country House Le Case Coloniche: This vacation home rental outside of Citta della Pieve is located in a rural location and has a terrace, a garden, and a barbecue grill to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Our travelers also rate Villa on the Umbria-Tuscany border—for families and friends—with a private pool as a favorite home for rent in Citta della Pieve.

How many vacation rentals are there in Citta della Pieve?

Choose from 38 Expedia vacation rentals in Citta della Pieve for a memorable vacation.

What can I see and do in Citta della Pieve?

Family-friendly attractions include Centro Servizi Turistici Citta della Pieve, whereas Val di Chiana is a spot to enjoy the outdoors. Other places in town to visit include Santa Maria dei Bianchi Oratory and Fontesecca.

What are vacation rentals like in Citta della Pieve?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Citta della Pieve. Vacation rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.