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

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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 modern kitchen with white cabinets, a gas stove, a microwave, and a dining area with a table and chairs.
A cozy living room with a stone wall, a staircase, and a view of the outside through a window.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.

1. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
AED 426
AED 516 total
includes taxes & fees
20 Oct - 21 Oct
Old medieval apartment
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.
A bedroom with a bed under a canopy, wooden beams on the ceiling, and a white 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.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
AED 332
AED 653 total
includes taxes & fees
13 Oct - 14 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 living room with a high wooden ceiling, a blue sofa, a white armchair, a small table with a candle, and a desk with a lamp and candlesticks.
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.

3. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
AED 518
AED 1,094 total
includes taxes & fees
13 Oct - 14 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 bedroom with a bunk bed, a flat-screen TV mounted on the wall, a bedside table, and a window with curtains.
A hallway with a herringbone floor pattern, grey walls, and a wooden ceiling beam.
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
AED 313
AED 601 total
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.
An aerial view of a property with a swimming pool, lounge chairs, and a large house surrounded by greenery.
A lush garden with a pool, a gazebo, and a view of distant trees and hills.
A bedroom with a metal bed frame, two bedside tables with lamps, a wooden window with shutters, and a wall-mounted light fixture.

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.
AED 736
AED 1,061 total
includes taxes & fees
1 Nov - 2 Nov
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
A view through a large arched window of a stone patio with a table and chairs, an umbrella, and lush greenery.
A rectangular pool with a stone border, surrounded by a grassy area and a row of sun loungers with umbrellas.
A kitchen with a large window, wooden cabinets, and a dining table with chairs.
A rustic dining area with a stone wall, wooden door, and a wooden table with chairs.

6. Glicini 1, holiday home with pool 30' from Florence

Glicini 1, holiday home with pool 30' from Florence
Tavarnelle Val di Pesa
United States
Joe M.
AED 602
AED 602 total
includes taxes & fees
20 Oct - 21 Oct
Glicini 1, holiday home with pool 30' from Florence
A narrow alleyway with brick walls, wooden barrels, and potted plants.
A historic town with medieval towers and buildings.
A courtyard with a hanging planter, potted plants, and a brick wall.
A wooden door with a plaque, an arched doorway, a checkered floor, a sofa, and a chair.

7. 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.
AED 407
AED 629 total
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 kitchen with wooden cabinets, a microwave, and a stove.
A landscaped garden with a swimming pool, a rock formation, and a fence.
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.

8. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
Germany
Johanna K.
AED 1,851
AED 2,271 total
includes taxes & fees
12 Nov - 13 Nov
Farmhouse in Chianti
A stone-walled room with a window overlooking a landscape.
A kitchen with wooden cabinets, a stone wall, and a built-in shelf with glassware.
A brick building with a large arched doorway and a small window.
A staircase with a metal railing leading to a higher level, a wooden barrel, and a stone wall.

9. Medieval Tower experience with Panoramic Rooftop, San Gimignano

Medieval Tower experience with Panoramic Rooftop, San Gimignano
San Gimignano City Centre
United States
mark M.
AED 1,646
AED 2,110 total
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 narrow corridor with a brick wall on the left, a staircase on the right, and a door at the far end.
A modern kitchen with white cabinets, a black countertop, a sink, and a coffee maker.
A modern kitchen with a wooden dining table, black chairs, and a black countertop.

10. 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.
AED 374
AED 634 total
includes taxes & fees
13 Oct - 14 Oct
THE EATER'S NEST - Unique in the Piazza del Campo
View all properties

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
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 8 days ago
Grand Hotel Baglioni

Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need a romantic vacation, we've got just the thing. 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're interested in staying near a particular destination, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
What's the best hotel for couples in Castellina in Chianti?
Lovely country house in the Chianti region, for 4 persons, near Siena is a favorite country house for couples, and features free WiFi and a garden. Another good option for your romantic getaway is Farmhouse in the Chianti "La Foresta 1" with swimming pool.
How many romantic hotels will we find 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, check out these details about year-round temperatures in Castellina in Chianti: The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.
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 Florence Airport, Peretola (FLR), which is the closest major airport located 23.2 mi (37.4 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.