Title: Book The Best Hotels in Montegrossi for 2025 from CA $91 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Montegrossi](https://expedia.ca/Montegrossi-Vacation-Rentals.d553248622859355230.Travel-Guide-VacationRentals)[Montegrossi Car Rentals](https://expedia.ca/Car-Rentals-In-Montegrossi.d553248622859355230.Car-Rental-Guide)[Montegrossi Vacation Packages](https://expedia.ca/Montegrossi.d553248622859355230.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Montegrossi from CA $91 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Montegrossi Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=APART_HOTEL) Spa [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=SPA_ON_SITE) Farm [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=AGRITOURISM) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&travelerType=family_friendly) Pool [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=POOL) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=APARTMENT) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=HOT_TUB) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=COTTAGE) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=PETS) Villa [](https://www.expedia.ca/Hotel-Search?destination=Montegrossi%2C+Gaiole+in+Chianti%2C+Tuscany%2C+Italy®ionId=553248622859355230&latLong=43.481644%2C11.455383&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=VILLA) ## Check prices for these dates Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248622859355230&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 6,043 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070779/e8636907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily self-serve breakfast (EUR 9 per person)](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070779/6a6d04cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070779/7c625dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070779/b19c7544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Loggia Villa Gloria - Adults Only Castelnuovo Berardenga 8.4/10 Very good (281) "This villa is in good location but not good managed at all. No teapot in the room" CA $96 CA $112 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Loggia-Villa-Gloria.h1070779.Hotel-Information) ![Sauna, hot tub, steam room, Turkish bath, body treatments](https://images.trvl-media.com/lodging/9000000/8200000/8198300/8198248/cb76be6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8200000/8198300/8198248/afd0837d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8200000/8198300/8198248/9cf69833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, Turkish bath, body treatments](https://images.trvl-media.com/lodging/9000000/8200000/8198300/8198248/0b1ab525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Gentiluomo Hotel & SPA Arezzo 8.6/10 Excellent (144) "Great hotel and awesome spa. The staff was super helpful. They helped with booking our taxis and tolerated our attempts at Italian. The room was clean and comfortable. " CA $87 CA $105 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Arezzo-Hotels-Hotel-Il-Gentiluomo.h8198248.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/f4558f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/84f971b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6216ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano Castelnuovo Berardenga 9.6/10 Exceptional (475) "Excellent staff, great food. " CA $176 CA $200 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/510521f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/a0449af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/2f59e0f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Living area](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/4dfdaf4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Del Cabreo Greve in Chianti 10/10 Exceptional (263) "We had a wonderful four day stay. Service is attentive, amenities are great, the property gardens were beautiful and the surrounding views breathtaking! I am already planning my next trip!" CA $320 CA $359 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/679da5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/18de298e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/dd9f1e7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/0cf3c295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Argiano Castelnuovo Berardenga 10/10 Exceptional (69) "Very comfortable stay. " CA $407 CA $461 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Borgo-Argiano.h21114825.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/1b4933fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/cbac26e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lapina Suite | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/06ea4b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bellavista | Living area](https://images.trvl-media.com/lodging/90000000/89240000/89237400/89237342/0461fb8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Club House Castelnuovo Berardenga 10/10 Exceptional (4) "The nicest and professional staff, cleanless as I never saw, the beauty of the landscape unbelievable..for sure I will go back" CA $735 CA $825 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-The-Club-House.h89237342.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/1d958423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/c9ee8535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/e06aa6e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277546/155c6de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Scopeto Wine & Country Relais Castelnuovo Berardenga 9.2/10 Wonderful (188) "This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint " CA $497 CA $563 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Borgo-Scopeto-Relais.h1277546.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/aaf98c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/70e53beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/079f0a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, located in a dependence, at 300 meters from the historic Villa, accessible with stairs](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/a4499de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torre a Cona Wine Estate Rignano sull'Arno 9.6/10 Exceptional (85) "The pool area and views were amazing. Also the food was excellent and the ambiance and experience was mesmerizing. We will travel to this location again!!" CA $381 CA $423 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Torre-A-Cona-Wine-Estate.h42059842.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c.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/2000000/1220000/1216500/1216478/ac1776a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Studio Suite | View from room](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/07f20b30.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/2000000/1220000/1216500/1216478/346cd924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo di Cortefreda Relais Barberino Tavarnelle 9.4/10 Exceptional (467) "Beautiful property and helpful staff. " CA $216 CA $247 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Private pool](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/3986de2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; international cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; international cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/92950714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Heritage)](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/48bd2186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COMO Castello Del Nero Barberino Tavarnelle 9.6/10 Exceptional (129) "Beautiful property in a stunning location. Large, well appointed rooms. A wonderful stay." CA $1,225 CA $1,361 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Couples treatment rooms, Turkish bath, body treatments, body wraps](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/b16ad5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/e302ad8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/f854e266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/9db7bc16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castel Monastero - The Leading Hotels of the World Castelnuovo Berardenga 8.8/10 Excellent (143) "Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back" CA $665 CA $748 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Castel-Monastero.h2589383.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/980000/976900/976812/bd38a523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/980000/976900/976812/3a3b1c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar, pool views, open daily](https://images.trvl-media.com/lodging/1000000/980000/976900/976812/57781f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/980000/976900/976812/06a833df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Albergo Del Chianti Greve in Chianti 8.6/10 Excellent (183) "Such a beautiful place to stay on the square. Walking trails are literally in the doorstep, dining options are plentiful and the staff were so friendly and helpful. " CA $145 CA $165 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Albergo-Del-Chianti.h976812.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/826b9811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/7531f1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salvadonica - Borgo del Chianti San Casciano in Val di Pesa 9.6/10 Exceptional (246) "Beautiful setting with delicious food and attentive staff " CA $264 CA $297 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/18000000/17420000/17418100/17418099/20b35a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17420000/17418100/17418099/aefa14ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Bedroom, Accessible, Hot Tub](https://images.trvl-media.com/lodging/18000000/17420000/17418100/17418099/4092261e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/18000000/17420000/17418100/17418099/e78ae170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Point Arezzo Park Hotel Arezzo 7.8/10 Good (144) " cheap, clean, new" CA $148 CA $173 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Arezzo-Hotels-A-Point-Arezzo-Park-Hotel.h17418099.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/23000000/22650000/22644800/22644742/40e40ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/23000000/22650000/22644800/22644742/16406fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/23000000/22650000/22644800/22644742/6f4e5fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/23000000/22650000/22644800/22644742/28bcd43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Pensione di Vignamaggio Panzano in Chianti 9.6/10 Exceptional (110) "Wonderful stay, highly recommend!!!" CA $241 CA $266 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-La-Pensione-Di-Vignamaggio.h22644742.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/72cf22f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Italian cuisine](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/aaf1d984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/f0b9ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3770000/3763200/3763111/0cec1f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Sabolini Colle di Val d'Elsa 9.2/10 Wonderful (185) "Beautiful location and hotel Staff were excellent - thank you" CA $179 CA $202 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Villa-Sabolini.h3763111.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/17000000/16330000/16322400/16322373/35dd60e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16330000/16322400/16322373/43fdec64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16330000/16322400/16322373/95045371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/17000000/16330000/16322400/16322373/9031f8d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo I Vicelli Adults Only Relais Bagno a Ripoli 9.2/10 Wonderful (45) "Very nice and well preserved estate in a stunning surrounding. Worth the detour, also because of the fantastic kitchen!" CA $234 CA $263 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Borgo-I-Vicelli-Country-Relais.h16322373.Hotel-Information) ![Indoor spa tub](https://images.trvl-media.com/lodging/5000000/4460000/4459100/4459020/e097a1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/5000000/4460000/4459100/4459020/fcc48187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![25-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/5000000/4460000/4459100/4459020/15898c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/5000000/4460000/4459100/4459020/92b373a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Squarcialupi Castellina in Chianti 9.8/10 Exceptional (68) "This was the most amazing place ever. The view, the staff, the breakfast, the location, the everything! " CA $268 CA $305 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Palazzo-Squarcialupi.h4459020.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1190000/1186800/1186799/b0e6cfa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1190000/1186800/1186799/64b641bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, hair dryer, slippers](https://images.trvl-media.com/lodging/2000000/1190000/1186800/1186799/1fc82107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1190000/1186800/1186799/bd2306cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda Il Gallo Greve in Chianti 9.4/10 Exceptional (53) "The property owner was very helpful explaining wineries location and local food! The in-house restaurant was excellent and convenient! " CA $183 CA $207 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Locanda-Il-Gallo.h1186799.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/4e848a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/2b5e075e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/3260acda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/7bd8c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Le Fontanelle Castelnuovo Berardenga 9.8/10 Exceptional (93) "We had a perfect stay at this hotel! 100% recommend. " CA $548 CA $619 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Le-Fontanelle.h1614881.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.ca/Hotel-Search?startDate=2025-10-14&endDate=2025-10-15®ionId=553248622859355230&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMontegrossi-Hotels.d553248622859355230.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMontegrossi-Hotels.d553248622859355230.Travel-Guide-Hotels) ### Stay near popular Montegrossi attractions [](https://expedia.ca/Castle-Of-Brolio-Hotels.0-l6249465-0.Travel-Guide-Filter-Hotels) #### Castle of Brolio You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and charming coffeehouses in this walkable area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6249465) ## More cheap stays in Montegrossi ![Piccolo Hotel Etruria](https://images.trvl-media.com/lodging/19000000/18180000/18174100/18174068/e41ea97c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Piccolo Hotel Etruria Via delle Donzelle, 3, Siena, SI CA $160 per night Oct 5 - Oct 6 7.8/10 Good! (358 reviews) [](https://expedia.ca/Siena-Hotels-Piccolo-Hotel-Etruria.h18174068.Hotel-Information) ![Porta Pispini Residence](https://images.trvl-media.com/lodging/39000000/38390000/38385000/38384931/463354ae_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Porta Pispini Residence Via Baldassarre Peruzzi 33, Siena, SI [Get rates](https://expedia.ca/Hotel-Search?startDate=14%2F10%2F2025&endDate=15%2F10%2F2025&selected=38384931&PinnedHotelID=38384931&HadPinnedHotel=true®ionId=553248622859355230) 9.4/10 Exceptional! (18 reviews) [](https://expedia.ca/Siena-Hotels-Porta-Pispini-Residence.h38384931.Hotel-Information) ![Cannon d'Oro](https://images.trvl-media.com/lodging/3000000/2530000/2525800/2525757/bda17ddf_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Cannon d'Oro Via Montanini 28, Siena, SI CA $75 per night Oct 26 - Oct 27 7.8/10 Good! (239 reviews) [](https://expedia.ca/Siena-Hotels-Cannon-DOro.h2525757.Hotel-Information) ![Albergo Centrale](https://images.trvl-media.com/lodging/53000000/52710000/52705700/52705677/350a0544_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Albergo Centrale Via Cecco Angiolieri 26, Siena, SI CA $174 per night Oct 1 - Oct 2 8.8/10 Excellent! (81 reviews) [](https://expedia.ca/Siena-Hotels-Albergo-Centrale.h52705677.Hotel-Information) ![Hotel Albergo Italia](https://images.trvl-media.com/lodging/23000000/22740000/22736200/22736103/7b6f90b7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Albergo Italia Via Trento, 36, Poggibonsi, SI CA $104 per night Oct 3 - Oct 4 8.4/10 Very Good! (42 reviews) [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Albergo-Italia.h22736103.Hotel-Information) ![Torre del Fuggisole](https://images.trvl-media.com/lodging/95000000/94900000/94897100/94897051/6b84e393_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Torre del Fuggisole Via di Fieravecchia 7, Siena, SI CA $194 per night Oct 29 - Oct 30 9.8/10 Exceptional! (35 reviews) [](https://expedia.ca/Siena-Hotels-Torre-Del-Fuggisole.h94897051.Hotel-Information) ## Recent reviews of Montegrossi hotels ![Hotel Athena](//images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg) ### Hotel Athena 5/5 Excellent "Very small room compared with our last visit, but comfortable foe one night stay." A verified traveller stayed at Hotel Athena Posted 6 days ago [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](//images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 5/5 Excellent "Beautiful property at an impressively reasonable price. E-Bike rentals on site were perfect to ride to vineyards nearby. The pool was amazing and the staff. The on site restaurant might have been my best meal in Italy! I would stay again in a heartbeat!" A verified traveller stayed at Hotel Borgo di Cortefreda Relais Posted 6 days ago [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Borgo Grondaie](//images.trvl-media.com/lodging/1000000/910000/905800/905710/58e23d32_y.jpg) ### Borgo Grondaie 5/5 Excellent "Lovely hotel a short walk from the train station but feels like it’s in the countryside. Huge supermarket at the end of the driveway for those self-catering. Pleasant grassy pool area that felt very peaceful. Large cool room with very comfortable bed. The staff were friendly, super helpful and accommodating. Would definitely stay again. " A verified traveller stayed at Borgo Grondaie Posted 7 days ago [](https://expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) ![NH Siena](//images.trvl-media.com/lodging/1000000/20000/15800/15716/9d41d91a_y.jpg) ### NH Siena 5/5 Excellent "Front desk staff were professional, kind and multilingual. Very helpful with storing luggage after checkout and help with printing museum tickets. Valet parking is easier than parking yourself at this location. Cost was €35." A verified traveller stayed at NH Siena Posted 7 days ago [](https://expedia.ca/Siena-Hotels-NH-Siena.h15716.Hotel-Information) ![La Certosa di Pontignano](//images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7_y.jpg) ### La Certosa di Pontignano 5/5 Excellent "Upscale service staff" A verified traveller stayed at La Certosa di Pontignano Posted 8 days ago [](https://expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Hotel Chiusarelli](//images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/a501ded1_y.jpg) ### Hotel Chiusarelli 5/5 Excellent "Beautiful place. Be mindful of stairs. " A verified traveller stayed at Hotel Chiusarelli Posted 8 days ago [](https://expedia.ca/Siena-Hotels-Hotel-Chiusarelli.h1110843.Hotel-Information) ![ Palazzo Ravizza](//images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/9acb6317_y.jpg) ### Palazzo Ravizza 5/5 Excellent "Stayed a very enjoyable three nights. Double room w/ garden view. “garden view” yes but also a stunning view of the Tuscan countryside. Breakfast buffet was bountiful and offered many options. Would stay again in a heartbeat!" A verified traveller from Kensington stayed at Palazzo Ravizza Posted 11 days ago [](https://expedia.ca/Siena-Hotels-Pensione-Palazzo-Ravizza.h1760168.Hotel-Information) ![Grand Hotel Continental Siena – Starhotels Collezione](//images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg) ### Grand Hotel Continental Siena – Starhotels Collezione 5/5 Excellent "If you pay attention to the hotel’s driving instructions, everything else will be 5 star. All of the staff is very accommodating to your every need. The rooms are European elegance with totally updated amenities. Breakfast buffet is fresh and hot with ample selections. Location is in the heart of beautiful Siena. " A verified traveller stayed at Grand Hotel Continental Siena – Starhotels Collezione Posted 12 days ago [](https://expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information) ![Hotel Borgo San Luigi](//images.trvl-media.com/lodging/1000000/530000/527600/527532/69a3ac66_y.jpg) ### Hotel Borgo San Luigi 5/5 Excellent Lovely stay "Lovely place and very helpful and friendly staff, especially at the bar/lunch area. The check-in process was flawless and very detailed, the grounds are stunning and the rooms are traditional yet it feels modern. Everything was clean and well kept. Opportunity to improve on reception’s English and not profiting from guests on Taxis rip off, if booking from the hotel. " A verified traveller stayed at Hotel Borgo San Luigi Posted 13 days ago [](https://expedia.ca/Monteriggioni-Hotels-Hotel-Borgo-San-Luigi.h527532.Hotel-Information) ## Frequently asked questions ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montegrossi. ### How can I save on a Montegrossi hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Montegrossi hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Montegrossi hotel? > Prices for hotels in Montegrossi often vary, but you can find a great deal from CA $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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[Poggio Alle Monache Hotels](https://www.expedia.ca/Poggio-Alle-Monache-Hotels.d553248622859413349.Travel-Guide-Hotels) - [Cheap Hotels in Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti-Hotels-Cheap-Hotels.0-0-d601693-tCheapHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti-Hotels-LGBT-Friendly-Hotel.0-0-d601693-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti-Hotels-Spa-Hotel.0-0-d601693-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti-Hotels-Wedding-Hotels.0-0-d601693-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti-Hotels-Winery-Hotel.0-0-d601693-tWineryHotel.Travel-Guide-Filter-Hotels) - [Radda in Chianti Hotels](https://www.expedia.ca/Radda-In-Chianti-Hotels.d601693.Travel-Guide-Hotels) - 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[Le Miccine](https://www.expedia.ca/Le-Miccine-Cavriglia.d553248621532500723.Vacation-Attraction) - [Visit Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti.dx601693) - [Visit Starda](https://www.expedia.ca/Starda.dx6285677) - [Visit Vertine](https://www.expedia.ca/Vertine.dx632712480144572416) - [Car rentals near Chianti Region](https://www.expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide) - [Car rental Radda in Chianti](https://www.expedia.ca/Car-Rentals-In-Radda-In-Chianti.d601693.Car-Rental-Guide) - [Easirent Rental Cars in Chianti Region](https://www.expedia.ca/Easirent-Car-Rentals-In-Chianti-Region.d603148-c1039.Car-Rental-Guide-Suppliers) - [Kk Leisure Rental Cars in Chianti Region](https://www.expedia.ca/KK-Leisure-Car-Rentals-In-Chianti-Region.d603148-c1133.Car-Rental-Guide-Suppliers) - [Chianti Region Vacation Rentals](https://www.expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals) - [San Sano Vacation Rentals](https://www.expedia.ca/San-Sano-Vacation-Rentals.d6285678.Travel-Guide-VacationRentals) - [Things to do in Chianti Region](https://www.expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities) - [Things to do in Gaiole in Chianti](https://www.expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities) - [Things to do in Lecchi in Chianti](https://www.expedia.ca/Things-To-Do-In-Lecchi-In-Chianti.d553248635974650979.Travel-Guide-Activities) - [Book Hotels in Montegrossi on Expedia.it](https://www.expedia.it/Montegrossi-Hotel.d553248622859355230.Guida-Viaggi-Hotel) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)