Colle di Val d'Elsa Vacation Homes

A historic town with a prominent hilltop church and a bell tower.

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Our top choices for Colle di Val d'Elsa holiday homes

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,136 total

includes taxes & fees

8 Nov - 9 Nov

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

2. Casa Vacanze Le Case

San Gimignano

Andrew

HK$794 total

includes taxes & fees

2 Nov - 3 Nov

A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

3. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

San Gimignano City Centre

HK$1,800 total

includes taxes & fees

2 Nov - 3 Nov

A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

4. Comfortable double room with a bathroom in the historic center of San Gimignano.

San Gimignano City Centre

HK$1,295 total

includes taxes & fees

1 Nov - 2 Nov

A rustic villa with a garden, a pond, and a mountainous backdrop.

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,533 total

includes taxes & fees

1 Nov - 2 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

6. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

HK$1,406 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a covered outdoor seating area and a brick pathway.

7. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

San Gimignano

Anne-Marie M.

HK$4,255 total

includes taxes & fees

1 Nov - 2 Nov

A balcony with a table and chairs overlooking a vineyard.

8. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

San Gimignano

Bruno G.

HK$4,587 total

includes taxes & fees

2 Nov - 3 Nov

A two-story house with a stone foundation, wooden shutters, and a covered porch with outdoor furniture.

9. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Casole d'Elsa

Anonymous traveller

HK$4,313 total

includes taxes & fees

25 Nov - 26 Nov

A glass on a wooden surface with a pool and a building in the background.

10. Apartment in Chianti With Pool ID 513

Casole d'Elsa

A stone building with a gravel path, outdoor seating, and greenery.

11. The Arch Among the Hills of Castellina

Topina

HK$2,231 total

includes taxes & fees

4 Nov - 5 Nov

A narrow alleyway with a stone archway leading to a building with a brick facade.

12. A Nest with a View - A Romantic Getaway Within the City Walls

Radicondoli

HK$1,358 total

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a bed, a vanity with a mirror, and LED strip lighting.

13. Siena Love Nest: Romantic Suite with Spa & Jacuzzi

Toscana

HK$1,540 total

includes taxes & fees

2 Nov - 3 Nov

A brick building with a garden, a metal fence, and a clear sky.

14. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,572 total

includes taxes & fees

15 Nov - 16 Nov

A view through a wooden door of a courtyard with stone walls and potted plants.

15. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,601 total

includes taxes & fees

2 Nov - 3 Nov

A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

16. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

San Gimignano

HK$2,603 total

includes taxes & fees

31 Oct - 1 Nov

A stone building with a hot tub, surrounded by greenery.

17. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

San Gimignano

Dale M.

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

18. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

HK$2,922 total

includes taxes & fees

27 Nov - 28 Nov

A horse grazing under a tree in a grassy area with a small building in the background.

19. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

Toscana

"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."

Shanti R.

HK$1,636 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk with a chair, a wardrobe, a mirror, a television, and two framed pictures on the wall.

20. A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.

San Gimignano City Centre

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Top Colle di Val d'Elsa Hotel Reviews

Hotel Athena

8/10 Good

"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"

Castelfalfi

10/10 Excellent

"Get ready to be impressed if you stay here. Every staff member from our arrival to our departure genuinely greeted us and welcomed us and many remembered our name. They always asked if we needed anything or offered help or suggestions in a genuine “we want to help way”. The concierge before our stay was ultra responsive, during our stay they were always present. You want attention to detail, Castelfalfi has it covered. Drinks are carefully made and delivered. Turn down service straightened the room, put little clothes under anything we had on the bathroom sink or room table, a new bookmark was left next to my book on the nightstand, cords were always wrapped and made to look tidy, I could go on and on. The food in the various restaurants was amazing. The little meat and cheese shop made a tremendous& fresh sandwich sliced up right in front of us on fresh baked bread. The view of sunset from the back deck had many guests out watching for good reason. The spa pool was great and the gym was pretty big. The breakfast buffet had everything you could want. Want fresh honey? There was a station with a honeycomb taken from their property…it drips fresh honey into a tray that empties into a bowl for you. The wine tasting was fun and delicious and worth it. Everything is on site and you will not want to leave the property during your stay or at the end of your trip. Castelfalfi- I hope and pray I return some day, thank you!!"

Il Chiostro del Carmine

10/10 Excellent

"Everything about this place is excellent. We had a wonderful stay and beautiful views of the sunrise! One thing to note is that you do have to take a flight of stairs to your room as there is no elevator. If you have luggage you may want to take this into consideration. We did and it was manageable!"

Hotel Borgo San Luigi

10/10 Excellent

"Borgo San Luis is a luxury destination! The four of us were treated as honored guests of great renown. The grounds were wide, varied, and immaculate. The breakfasts were special events for us foodies, and the swimming pool was refreshing even in October!. Parking was free, secure, and accessible. We easily saw why the Borgo was a destination for the weddings, feasts, and meetings that were taking place at the time of our visit -- but they were never intrusive. The staff were multi-lingual and honestly could not do enough for us. Should you ever desire a dream from which that you did not want to awaken, visit Borgo San Luis."

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