A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Hotel Guide - Romantic Hotels in Castellina in Chianti, Tuscany

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Check availability on Castellina in Chianti Romantic Hotels

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Castellina in Chianti romantic hotels

A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.
A staircase with a stone wall on one side and a dark wooden door on the other.
A cozy living room with a stone wall, a staircase, and a view of the outside through a window.

1. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
€130
includes taxes & fees
12 Oct - 13 Oct
Old medieval apartment
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.
An outdoor patio with a round table and chairs, surrounded by stone walls and a tall tree.
A rustic dining area with a wooden table and chairs, a fireplace, and a brick floor.
A bedroom with a bed under a canopy, wooden beams on the ceiling, and a white door.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
€164
includes taxes & fees
12 Oct - 13 Oct
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A stone building with a terrace, a table with chairs, and a red umbrella.
A courtyard with stone buildings, a gravel path, and potted plants.
A vineyard with terracotta pots and stone walls, overlooking a hilly landscape with vineyards and distant hills.
A living room with a tiled floor, a blue sofa, a beige armchair, a small round table, a television, and a wooden ceiling beam.

3. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
€275
includes taxes & fees
12 Oct - 13 Oct
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.
A hallway with a herringbone floor pattern, grey walls, and a wooden ceiling beam.
A bedroom with a bunk bed, a flat-screen TV mounted on the wall, a bedside table, and a window with curtains.
A modern kitchen with white cabinets, a microwave, and a glass dining table with blue chairs.

4. Colle di Val d'Elsa - Siena - Blue Apartment - C

Colle di Val d'Elsa - Siena - Blue Apartment - C
Colle di Val d'Elsa
United States
ALLAN
€150
includes taxes & fees
14 Oct - 15 Oct
Colle di Val d'Elsa - Siena - Blue Apartment - C
A two-story stone house with a swimming pool, surrounded by greenery and a clear sky.
A bedroom with a metal bed frame, two bedside tables with lamps, a wooden window with shutters, and a wall-mounted light fixture.
An aerial view of a property with a swimming pool, lounge chairs, and a large house surrounded by greenery.
A stone wall with potted plants and flowers, surrounded by greenery and a stone building in the background.

5. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
Italy
giuseppe z.
€267
includes taxes & fees
1 Nov - 2 Nov
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
A narrow alleyway with brick walls, wooden barrels, and potted plants.
A wooden door with a plaque, an arched doorway, a checkered floor, a sofa, and a chair.
A courtyard with a hanging planter, potted plants, and a brick wall.
A historic town with medieval towers and buildings.

6. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
United States
Marilyn H.
€156
includes taxes & fees
14 Oct - 15 Oct
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
A swimming pool with a colorful inflatable ring and a water fountain.
A rustic villa with a gravel driveway, surrounded by olive trees and a clear blue sky.
A neatly made bed with a purple pillow and two folded towels, flanked by two bedside tables with lamps, in a room with a simple, clean design.
A landscaped garden with a swimming pool, a rock formation, and a fence.

7. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
Germany
Johanna K.
€512
includes taxes & fees
12 Oct - 13 Oct
Farmhouse in Chianti
A stone-walled room with a window overlooking a landscape.
A table set with a bottle and glasses, overlooking a historic tower and a scenic valley.
A staircase with a metal railing leading to a higher level, a wooden barrel, and a stone wall.
A brick building with a large arched doorway and a small window.

8. Medieval Tower experience with Panoramic Rooftop, San Gimignano

Medieval Tower experience with Panoramic Rooftop, San Gimignano
San Gimignano City Centre
United States
mark M.
€525
includes taxes & fees
7 Nov - 8 Nov
Medieval Tower experience with Panoramic Rooftop, San Gimignano
A large, arched wooden door with a sign above it reading "AXA ASSICURAZIONI AGENZIA GENERALE".
A modern kitchen with a wooden dining table, black chairs, and a black countertop.
A modern bedroom with a curved bed, a framed picture on the wall, and a hanging light fixture.
A narrow corridor with a brick wall on the left, a staircase on the right, and a door at the far end.

9. THE EATER'S NEST - Unique in the Piazza del Campo

THE EATER'S NEST - Unique in the Piazza del Campo
Siena City Centre
United States
Benjamin C.
€154
includes taxes & fees
13 Oct - 14 Oct
THE EATER'S NEST - Unique in the Piazza del Campo
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Top Castellina in Chianti Hotel Reviews

The Market Urban Hotel

The Market Urban Hotel

10/10 Excellent
"Couldn’t have asked for any more. Great location, attentive staff before and during stay. Breakfast was perfect before a long day. The room was great - 5th floor if you can get it feels like a PENTHOUSE apartment!"
Grant 3-night trip
Posted 2 days ago
The Market Urban Hotel
Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Buena ubicacion, habitacion limpia. Desayuno bueno, delicioso y barato. El personal del hotel muy amable y siempre dispuesto a ayudar. Definotivamente lo recomiendo 100%.🌻"
Sally 2-night trip
Posted 3 days ago
Plus Florence - Hostel
Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"Staff was friendly and accommodating! Rooms were very clean and SPACIOUS! Would definitely return!"
Suzette 1-night trip
Posted 6 days ago
Grand Hotel Cavour
Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Great hotel within walking distance of the historic centre of Florence. Helpful and knowledgeable staff. Amazing views from the rooftop bar/ restaurant. Thank you"
Emma 4-night trip
Posted 7 days ago
Grand Hotel Baglioni

Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need a romantic escape, we'd like to help you plan for it. Our guests also enjoy Castellina in Chianti for its wineries and countryside. You might consider checking out some of the nearby sights and attractions such as Castellina Fortress, Archaeological Museum of Chianti or Walls of Monteriggioni. If you'd like to stay close to a particular destination, you can sort by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
What's the best accommodation for a romantic holiday in Castellina in Chianti?
Lovely country house in the Chianti region, for 4 persons, near Siena is a favourite country house for couples, and features free WiFi and a garden.
How many romantic hotels are there in Castellina in Chianti?
Expedia has 5 romantic Castellina in Chianti hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Castellina in Chianti?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Castellina in Chianti: The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castellina in Chianti is 935 mm.
What is there to do in Castellina in Chianti?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Castellina in Chianti. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Castellina in Chianti for its wineries. Castellina Fortress, Archaeological Museum of Chianti and Walls of Monteriggioni are worth a stop when you're out and about.
What's the best way to get to Castellina in Chianti and around town during my romantic getaway?
These transportation options in Castellina in Chianti might help your romantic trip get off to a smooth start: Make your way to Castellina in Chianti with a flight to Peretola Airport (FLR), which is the closest major airport located 23.2 mi (37.4 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.