Chianti Region Romantic Vacations

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Top Romantic vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Hotel Palazzo San Lorenzo & SPA
Villa San Lucchese
Borgo San Felice Resort
COMO Castello Del Nero
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5* Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Borgo San Felice Resort
COMO Castello Del Nero
Hotel Le Fontanelle
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3 Night Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Hotel Palazzo San Lorenzo & SPA
Villa San Lucchese
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See all available trips from Tokyo to Chianti Region
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Top Romantic Chianti Region Hotels

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano
  • 5 min drive from Tenuta Torciano Winery
Romance awaits at this villa, which features a garden and a hot tub. Couples will appreciate the in-room fireplaces and outdoor pool.
10/10 Exceptional! (120 reviews)

Couples like: hot tub, fireplace

Travelers say...
"Beautiful property. Spacious. Well equipped kitchen. Very accommodating host. Great location. Clean rooms. Cleaning service included. Only negative was the heat was turned off for the season but we had a few cold days. The stone house retains the cold."

Reviewed on Jun 3, 2026

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

4 out of 5
Via Roma 33 Radda in Chianti SI
  • 44 min drive from Tenuta Torciano Winery
Book a stay at this romantic hotel, featuring a spa and in-room massages. Couples will appreciate the hot tub, al fresco dining, and wine tasting rooms.
9.2/10 Wonderful! (289 reviews)

Couples like: full-service spa, couples spa treatments, al fresco dining, hot tub

Travelers say...
"The room was large and roomy and quiet. The breakfast was great! And the breakfast staff were very nice and helpful. The workout room was small but. Equipped for what we needed and there was never anyone else using it."

Reviewed on Jun 11, 2026

Palazzo Leopoldo Dimora Storica & Spa
COMO Castello Del Nero

COMO Castello Del Nero

5 out of 5
Strada Spicciano 7 Barberino Tavarnelle FI
  • 18 min drive from Tenuta Torciano Winery
For a romantic stay, consider this upscale hotel, featuring a spa, a Michelin star restaurant, and a garden. Couples will appreciate the hot tub and Egyptian ...
9.6/10 Exceptional! (137 reviews)

Couples like: full-service spa, couples spa treatments, Michelin star restaurant, hot tub

Travelers say...
"Everything was top notch and the food was amazing"

Reviewed on May 31, 2026

COMO Castello Del Nero
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.