Title: Montechiaro Vacation Rentals from $93: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635975868650&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=553248635975868650&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=553248635975868650&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=553248635975868650&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Montechiaro vacation rentals

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/f0bca152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa | Living area | 24-inch flat-screen TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/58622732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/5c9c109c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/65f08668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury resort in the Tuscan countryside

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

Trequanda

$215 nightly

$240 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

![La casa di Jakin | Terrace/patio](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/48f6b5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa di Donna Lisa | View from room](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/f5ed0303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa di Bohaz | View from room](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/630eb39a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![La casa dell'Architetto | Living area | 43-inch flat-screen TV with digital channels](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139702/0f87b43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tenuta Cantona

[](https://www.expedia.com/Casole-DElsa-Hotels-Tenuta-Cantona.h100139702.Hotel-Information)

Casole d'Elsa

$229 nightly

$254 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Casole-DElsa-Hotels-Tenuta-Cantona.h100139702.Hotel-Information)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/7e336ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/a00997c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/35e78bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/3c123570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information)

Monteaperti

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ian F.

$190 nightly

$196 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/8dbfb990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/236bbc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/c7f9cf0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96940000/96934300/96934275/7531d9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Albergo Diffuso Borgo Santo

[](https://www.expedia.com/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

Asciano

$218 nightly

$246 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Asciano-Hotels-Albergo-Diffuso-Borgo-Santo.h96934275.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/190e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/b53ae9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Single Room | Premium bedding, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/914c3e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Pozzo di Sant'Andrea

[](https://www.expedia.com/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

Siena

9.8/10

Exceptional

(16 reviews)

"Great host, lovely place near Siena"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Prem

$94 nightly

$109 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/cb376ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, 1 Bedroom, Terrace | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/ccba610a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (for 4 - 6 People) | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/4cdc2384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620800/97797fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Antico Borgo Poggiarello

[](https://www.expedia.com/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.Hotel-Information)

Monteriggioni

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

James Bakley

$169 nightly

$189 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Monteriggioni-Hotels-Antico-Borgo-Poggiarello.h3620800.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/cdb3c15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/396ff949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | In-room dining](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/424f0a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Garden View | Premium bedding, memory foam beds, minibar, in-room safe](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/3a6f7416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Coroncina Lodging

[](https://www.expedia.com/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

Siena

10/10

Exceptional

(42 reviews)

"Fantastic place, and I highly recommend it."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hassan

$131 nightly

$149 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/782fdb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/cdd9a264.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms, Garden View (Maria) | Living room | Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/667a06a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11040000/11031400/11031336/8b91ef4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo Lucignanello Bandini

[](https://www.expedia.com/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.Hotel-Information)

Montalcino

9.4/10

Exceptional

(12 reviews)

"Beautiful stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marc

$311 nightly

$352 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Montalcino-Hotels-Borgo-Lucignanello-Bandini.h11031336.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/eab05df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Concierge desk](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/bdf789e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/d37077fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Double Room, 1 Double Bed | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/13000000/12650000/12642600/12642590/c7b333e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa di Campagna in Toscana

[](https://www.expedia.com/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.Hotel-Information)

Sovicille

9.4/10

Exceptional

(21 reviews)

"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Alasdair

$96 nightly

$109 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Sovicille-Hotels-Casa-Di-Campagna-In-Toscana.h12642590.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/7fe98579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment | Private kitchen | Oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/53d9424a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/a763977c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/65f6d95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tuscasì Aparthotel

[](https://www.expedia.com/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

Sovicille

9.0/10

Wonderful

(26 reviews)

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sergey

$82 nightly

$93 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/3c3931cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/53f64e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/6901a1c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/05c157ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riserva di Fizzano Residence

[](https://www.expedia.com/Castellina-In-Chianti-Hotels-Riserva-Di-Fizzano-Residence.h3522769.Hotel-Information)

Castellina in Chianti

9.8/10

Exceptional

(25 reviews)

"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eileen

$199 nightly

$221 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/Castellina-In-Chianti-Hotels-Riserva-Di-Fizzano-Residence.h3522769.Hotel-Information)

![Studio, Patio, Ground Floor | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/291b1398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, Patio, Ground Floor | Private kitchen | Fridge, stovetop, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/04effc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/d64344d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom, Patio (3 people) | Frette Italian sheets, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2530000/2524600/2524503/dd9dbe0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fullino Nero

[](https://www.expedia.com/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information)

Siena

9.6/10

Exceptional

(50 reviews)

"Great stay! Clean rooms with air conditioning. Beautiful grounds "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christian

$101 nightly

$116 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Siena-Hotels-Fullino-Nero.h2524503.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d05582b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/a8ccbf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Poggio dell'Eremita

[](https://www.expedia.com/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

Sinalunga

10/10

Exceptional

(59 reviews)

"Fantastic place! Great location. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Paul Q.

$178 nightly

$180 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

![Villa, Air conditioning, Courtyard View | Exterior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6b3321e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/fee64891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/405723b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/127000000/126450000/126444900/126444856/6427b5b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Montecastello

[](https://www.expedia.com/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

Monteriggioni

$169 nightly

$190 total

Apr 3 - Apr 4

Total with taxes and fees

[](https://www.expedia.com/Monteriggioni-Hotels-Villa-Montecastello.h126444856.Hotel-Information)

![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/98406b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/277a67f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/a8ce016d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/521d6cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castello di Gargonza

[](https://www.expedia.com/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

Monte San Savino

9.2/10

Wonderful

(40 reviews)

"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David

$236 nightly

$265 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/1e065a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/54bc2210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/d353f2da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33150000/33140400/33140330/c5fb0a70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ca' Bianca Tuscany Relais

[](https://www.expedia.com/Siena-Hotels-Ca-Bianca.h33140330.Hotel-Information)

Siena

10/10

Exceptional

(43 reviews)

"Great time, perfect property and location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher

$209 nightly

$235 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Siena-Hotels-Ca-Bianca.h33140330.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms, Terrace (3 levels) | Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/16d2ada0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/f58a3308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/946f4e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bosco della Spina

[](https://www.expedia.com/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

Murlo

9.6/10

Exceptional

(170 reviews)

"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Lizl

$84 nightly

$101 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/ce6a104a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Suite | Frette Italian sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/c33da520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Couples treatment rooms, facials, massages](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/4c8f3824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6029600/6029534/73ef5376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo Argenina

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-La-Pieve-Marsina.h6029534.Hotel-Information)

Gaiole in Chianti

9.8/10

Exceptional

(22 reviews)

"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Massimo

$175 nightly

$202 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Gaiole-In-Chianti-Hotels-La-Pieve-Marsina.h6029534.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526513/8b9cc25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526513/5da34b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526513/24a39010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526513/92a467e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Borgo Il Poggiaccio

[](https://www.expedia.com/Sovicille-Hotels-Borgo-Il-Poggiaccio.h2526513.Hotel-Information)

Sovicille

8.8/10

Excellent

(65 reviews)

"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A\*\*\*"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dean

$211 nightly

$237 total

Apr 28 - Apr 29

Total with taxes and fees

[](https://www.expedia.com/Sovicille-Hotels-Borgo-Il-Poggiaccio.h2526513.Hotel-Information)

![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/258f72ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/920701e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Condo (Casa Palei B) | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/c8b78159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room (Camera 2) | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/3000000/2440000/2432300/2432264/38f4bf63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa di Sotto

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

Castelnuovo Berardenga

9.4/10

Exceptional

(28 reviews)

"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Amelia

$151 nightly

$167 total

Apr 29 - Apr 30

Total with taxes and fees

[](https://www.expedia.com/Castelnuovo-Berardenga-Hotels-Villa-Di-Sotto.h2432264.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-12&endDate=2026-04-13&regionId=553248635975868650&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VILLA)

Aparthotels

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Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=APARTMENT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CONDO)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=CHALET)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Montechiaro%2C+Siena%2C+Tuscany%2C+Italy&regionId=553248635975868650&latLong=43.332339%2C11.404635&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=RESIDENCE)

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## Top Montechiaro Hotel Reviews

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg)

###  Palazzo Ravizza

10/10 Excellent

"Everything here was excellent. Would highly recommend. "

[](https://expedia.com/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information)

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/f43eb5fd_y.jpg)

### Hotel Chiusarelli

8/10 Good

"The hotel was just outside of the town, so the location was good. It was a beautiful property. The breakfast was good. Just be prepared to walk stairs. No lifts. But overall, good. "

[](https://expedia.com/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information)

![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/7ece5a56_y.jpg)

### Villa Scacciapensieri Boutique Hotel

8/10 Good

"Stayed in this villa for a couple of nights. It’s a great option if you’re looking to escape the hustle and bustle of the city center. The location is lovely, with birds chirping in the background. The rooms were small, but they had all the necessary amenities for travelers. I had dinner and breakfast once each day. While the food was sufficient, I think it would be better to have more options given the 4-star rating of the property. The staff members were helpful and friendly."

[](https://expedia.com/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information)

![NH Siena](https://images.trvl-media.com/lodging/1000000/20000/15800/15716/w3840h2562x0y0-25695984_y.jpg)

### NH Siena

10/10 Excellent

"I didn't use it. I only stayed one night."

[](https://expedia.com/Siena-Hotels-NH-Siena.h15716.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/e3da527a_y.jpg)

### Hotel Italia

10/10 Excellent

"Very close to the bus and train station, lovely staff, clean room but a bit too warm even in February and no water kettle in the room, which was a bit surprising. "

[](https://expedia.com/Siena-Hotels-Hotel-Italia.h996973.Hotel-Information)

![Hotel Minerva](https://images.trvl-media.com/lodging/1000000/800000/800000/799995/bc9bd928_y.jpg)

### Hotel Minerva

8/10 Good

"Property was clean a tidy, was a little dated but still nice, view over Siena from the terrace was stunning. Staff were helpful and friendly giving us a map and guide of places of interest in the town. Included breakfast had great options and car park was convenient and safe."

[](https://expedia.com/Siena-Hotels-Hotel-Minerva.h799995.Hotel-Information)

![La Certosa di Pontignano](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8b3eb5da_y.jpg)

### La Certosa di Pontignano

6/10 Okay

"Here is a polished version of your review with improved grammar and structure, keeping your message clear and balanced: --- Great and beautiful place. The food is also very good, and the overall atmosphere is charming. However, the bed was terrible. The mattress was old, and the springs made it very uncomfortable, so I couldn’t sleep well. I’ve stayed in many different hotels and have never experienced such a bad bed. I understand that the concept and vibe of the place are meant to feel historic or classic, but for a property of this level, the bed should match the quality of the rest of the experience. Upgrading the mattresses would make a big difference."

[](https://expedia.com/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information)

![Four Points by Sheraton Siena](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/e65a78e2_y.jpg)

### Four Points by Sheraton Siena

6/10 Okay

"The air conditioning was bad. I was perspiring during my bed time. Other things were ok. Ample parking. "

[](https://expedia.com/Siena-Hotels-Four-Points-By-Sheraton-Siena.h852305.Hotel-Information)

![Borgo Scopeto Wine & Country Relais](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/133e09c8_y.jpg)

### Borgo Scopeto Wine & Country Relais

10/10 Excellent

"The Sommelier was outstanding, super knowledgeable and personable. He made the tasting and dinning experience unforgettable! "

[](https://expedia.com/Castelnuovo-Berardenga-Hotels-Borgo-Scopeto-Relais.h1277546.Hotel-Information)

## Find out more about Montechiaro

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

**Montechiaro vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Montechiaro. 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 Montechiaro 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 $93 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 Montechiaro rentals**

At Expedia, we put the best Montechiaro 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 Montechiaro 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 Montechiaro 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 Montechiaro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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## Frequently asked questions

### Can I find a vacation rental in Montechiaro?

### What are some of the best vacation home rentals that Montechiaro has to offer?

### What’s there to see and do in Montechiaro?

### What’s a vacation rental in Montechiaro like?