A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Romantic Hotels & Resorts in Chianti Region from NZ$199

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region Romantic Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Chianti Region romantic hotels

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.
A rustic dining area with a wooden table and chairs, a fireplace, and a brick floor.
A rustic dining area with a wooden table, blue chairs, a brick floor, a sofa, and a fireplace.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
NZ$316
includes taxes & fees
21 Oct - 22 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 living room with a tiled floor, a blue sofa, a beige armchair, a small round table, a television, and a wooden ceiling beam.
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.

2. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
NZ$525
includes taxes & fees
21 Oct - 22 Oct
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A two-story building with a balcony, surrounded by palm trees and a well-maintained garden with red flowers.
A hallway with a wooden archway, a bench, a rug, and a table with a book and flowers.
A stone pathway leading to a building with a yellow facade and green shutters.

3. Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B

Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
United States
Lynn P.
NZ$268
includes taxes & fees
20 Oct - 21 Oct
Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A bedroom with a bed, a nightstand, a lamp, a closet with shelves, and a spiral staircase.
A spiral staircase with a metal railing, a white chair, and framed pictures on the wall.
Outdoor spa tub

4. Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B

Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
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 staircase with a stone wall on one side and a dark wooden door on the other.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.

5. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
NZ$250
includes taxes & fees
29 Oct - 30 Oct
Old medieval apartment
A stone building with a courtyard, outdoor seating, and potted plants.
A kitchen with wooden cabinets, a stove, a large window, and a recycling bin.
A cozy living room with a fireplace, a floral armchair, a white sofa, and large windows.
A rustic dining area with a wooden table and chairs, a fireplace, and a large cabinet with glass doors.

6. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
United States
Christine F.
NZ$591
includes taxes & fees
21 Oct - 22 Oct
Sorbeto Vacation Home
A view through a large arched window of a stone patio with a table and chairs, an umbrella, and lush greenery.
A two-story building with a yellow facade, multiple windows, and a garden in front.
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.

7. 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.
NZ$292
includes taxes & fees
20 Oct - 21 Oct
Glicini 1, holiday home with pool 30' from Florence
A modern bedroom with a curved bed, a large mirror, and a jungle-themed mural.
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.
A modern kitchen with white cabinetry, a microwave, a sink, and a coffee maker.
A modern hotel corridor with a light-colored floor, a wooden ceiling, and a door leading to a bathroom.

8. Colle di Val d'Elsa - Siena - White Apartment - D

Colle di Val d'Elsa - Siena - White Apartment - D
Colle di Val d'Elsa
NZ$312
includes taxes & fees
20 Oct - 21 Oct
Colle di Val d'Elsa - Siena - White Apartment - D
A poolside setting with two drinks, a tray with snacks, and a white umbrella.
A table set outdoors with a view of a lush green landscape and mountains in the background.
A lush green landscape with a variety of trees and a clear blue sky.
A bedroom with a wooden bed, two bedside tables with lamps, a chandelier, and a wardrobe.

9. Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi

Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
Reggello
France
Jean-marc L.
NZ$199
includes taxes & fees
18 Oct - 19 Oct
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
A poolside setting with two glasses of red drink, a tray with chips and olives, and a white umbrella.
A yellow building with a balcony, surrounded by green grass and flowering trees.
A patio with a table and chairs, surrounded by greenery and a view of hills.
A bedroom with a bed, a bathroom with a shower, and a view of a garden and mountains.

10. Tuscany countryside appartment with pool

Tuscany countryside appartment with pool
Reggello FI
NZ$239
includes taxes & fees
18 Oct - 19 Oct
Tuscany countryside appartment with pool
View all properties

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 6 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 2 weeks ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."
Tereza 2-night trip
Posted 3 weeks ago
Villa Le Barone
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 1 month ago
COMO Castello Del Nero

Explore a world of travel with Expedia