San Chimento Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for San Chimento vacation rentals

Breakfast meal
B&B Il Corso

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (191)
"Safe, clean, close to all attractions"
Canada
Carlo
$81 nightly
The price is $93
Dec 14 - Dec 15
Total with taxes and fees
B&B Il Corso
Room amenity
Siena Vip

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
$93 nightly
The price is $107
Jan 6 - Jan 7, 2026
Total with taxes and fees
Siena Vip
Exterior
PALAZZO DEL PAPA

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$124 nightly
The price is $142
Dec 14 - Dec 15
Total with taxes and fees
PALAZZO DEL PAPA
Balcony
Palazzo al Torrione 2

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
$115 nightly
The price is $132
Dec 15 - Dec 16
Total with taxes and fees
Palazzo al Torrione 2
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very Good, (334)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel
Tasting room
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (191)
"Great location and friendly staff. "
United States
Parissa
$150 nightly
The price is $170
Jan 4 - Jan 5, 2026
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe
Tenuta Sant'Ilario

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
$97 nightly
The price is $111
Dec 16 - Dec 17
Total with taxes and fees
Tenuta Sant'Ilario
Restaurant
B&B Dei Rossi

Townhouse in Siena City Centre

B&B Dei Rossi
8.2 out of 10, Very Good, (18)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
$78 nightly
The price is $90
Dec 14 - Dec 15
Total with taxes and fees
B&B Dei Rossi
Property grounds
Domus il Palio B&B

Townhouse in Ravacciano

Domus il Palio B&B
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
$61 nightly
The price is $72
Jan 11 - Jan 12, 2026
Total with taxes and fees
Domus il Palio B&B
Terrace/patio
Casa di Campagna in Toscana

Townhouse in Sovicille

Casa di Campagna in Toscana
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Triple Room, Balcony, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Townhouse in Siena City Centre

Al Mercato B&B
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
$69 nightly
The price is $80
Dec 15 - Dec 16
Total with taxes and fees
Al Mercato B&B
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

Townhouse in Barberino Tavarnelle

La Locanda di Pietracupa
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
$108 nightly
The price is $123
Dec 15 - Dec 16
Total with taxes and fees
La Terrazza Sul Campo Rooming House
Exterior
Il Pozzo di Sant'Andrea

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
View from property
Antica Pieve B&B

Townhouse in Barberino Tavarnelle

Antica Pieve B&B
9.4 out of 10, Exceptional, (14)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
$112 nightly
The price is $128
Jan 10 - Jan 11, 2026
Total with taxes and fees
Antica Pieve B&B
City view
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
$85 nightly
The price is $98
Dec 14 - Dec 15
Total with taxes and fees
Regis Condo
Free daily buffet breakfast
Terre di Baccio

Townhouse in Greve in Chianti

Terre di Baccio
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$256 nightly
The price is $286
Dec 27 - Dec 28
Total with taxes and fees
Terre di Baccio
Exterior
Palazzo Masi

Townhouse in Siena City Centre

Palazzo Masi
8.8 out of 10, Excellent, (84)
"Very friendly and attentive, a very clean place and its location is excellent. "
United States
Gloria
$96 nightly
The price is $110
Jan 2 - Jan 3, 2026
Total with taxes and fees
Palazzo Masi
Exterior
Villa le Camelie Siena

Townhouse in Petriccio

Villa le Camelie Siena
8.6 out of 10, Excellent, (8)
"Nice for the price. Would stay there again."
United States
Mark
$91 nightly
The price is $105
Dec 14 - Dec 15
Total with taxes and fees
Villa le Camelie Siena
Premium bedding, down comforters, pillowtop beds, minibar
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$69 nightly
The price is $79
Dec 20 - Dec 21
Total with taxes and fees
Tuscasì Aparthotel
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 San Chimento Hotel Reviews

Villa del Sole Siena

Villa del Sole Siena

10/10 Excellent
"Amazing rooms and service!!"
Janet 1-night trip
Posted 5 days ago
Villa del Sole Siena

Find out more about San Chimento

Everything you need to know about San Chimento 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 San Chimento 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 San Chimento vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Chimento vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Chimento. 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 San Chimento 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 $79 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 San Chimento rentals

At Expedia, we put the best San Chimento 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 San Chimento 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 San Chimento 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 San Chimento. 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

Are there vacation rentals in San Chimento?

Yes, we give you a choice of vacation rentals close to popular points of interest in San Chimento, or you can go with a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in San Chimento?

Farmhouse in the heart of the real chiantishire: Visitors like this San Chimento vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in San Chimento?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Val di Merse. Monteriggioni Castle and Museo del Cristallo di Colle di Val d'Elsa are a couple of places you'll find in the larger area.

What’s a vacation rental in San Chimento like?

Vacation rentals are private properties where you can stay for short or long periods in San Chimento. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.