San Chimento Vacation Rentals

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for San Chimento vacation rentals

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
$170 nightly
The price is $191
May 17 - May 18
Total with taxes and fees
Villa Montecastello
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
$163 nightly
The price is $179
May 18 - May 19
Total with taxes and fees
Villa di Sotto
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (28 reviews)
"We loved it!"
United States
Juliette
$189 nightly
The price is $210
May 21 - May 22
Total with taxes and fees
Riserva di Fizzano Residence
Honeymoon Apartment, Vineyard View, Courtyard Area | Living area | 45-inch Smart TV with digital channels, TV

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$319 nightly
The price is $355
May 15 - May 16
Total with taxes and fees
Terre di Baccio
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
$178 nightly
The price is $199
Jun 12 - Jun 13
Total with taxes and fees
Antico Borgo Poggiarello
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
$145 nightly
The price is $169
May 17 - May 18
Total with taxes and fees
Villa Curina Resort
1 bedroom, free WiFi, bed sheets

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
$194 nightly
The price is $200
May 14 - May 15
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
$267 nightly
The price is $303
May 21 - May 22
Total with taxes and fees
Borgo Argenina
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (22 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
$102 nightly
The price is $116
May 17 - May 18
Total with taxes and fees
Casa di Campagna in Toscana
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$80 nightly
The price is $92
May 18 - May 19
Total with taxes and fees
Tuscasì Aparthotel
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
$163 nightly
The price is $188
May 23 - May 24
Total with taxes and fees
L' Eroico
Daily continental breakfast for a fee

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (123 reviews)
"Excellent location on heart of Siena .. staff were lovely"
United Kingdom
Thomas
$261 nightly
The price is $292
May 14 - May 15
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
$105 nightly
The price is $120
May 25 - May 26
Total with taxes and fees
Il Pozzo di Sant'Andrea
Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
$816 nightly
The price is $821
Jun 8 - Jun 9
Total with taxes and fees
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (437 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
$140 nightly
The price is $159
May 14 - May 15
Total with taxes and fees
Siena Vip
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
$210 nightly
The price is $236
May 17 - May 18
Total with taxes and fees
Borgo Il Poggiaccio
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (171 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
$120 nightly
The price is $142
May 21 - May 22
Total with taxes and fees
Bosco della Spina
8 outdoor pools

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
$816 nightly
The price is $907
May 25 - May 26
Total with taxes and fees
Villa Marcolina
Apartment, 1 Bedroom, Garden View | View from room

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
$157 nightly
The price is $178
Jun 9 - Jun 10
Total with taxes and fees
La Coroncina Lodging
Business Room, 1 Bedroom | Down comforters, desk, cribs/infant beds, rollaway beds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (87 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
$83 nightly
The price is $97
May 27 - May 28
Total with taxes and fees
Domus il Palio B&B
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 Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"We loved staying here and the staff was amazing. Unfortunately the weather didn't allow us to enjoy being outside in their gorgeous gardens much but we did have some spectacular views of Siena when we did. We didn't realize when we booked how far from city centre we would be, but the good thing was that the bus picked us up at the bottom of the driveway and for 1.70 each took us to the city centre . Also, even though the loft in our unit was beautiful, i didn't expect that the washroom would be downstairs which wasn't so convenient in the middle of the night. Breakfast buffet was great and cappuccino and café latte made for us upon request, was very delicious"
sara 2-night trip
Posted 12 hours ago
Villa Scacciapensieri Boutique Hotel

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 $54 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?

Borgo Argiano: Visitors like this San Chimento vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

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 Sentierelsa Trail. 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.