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4 Night Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.

Hotel Palazzo San Lorenzo & SPA

￥210,028

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Tokyo (HND) to Florence (FLR)

9.4/10 Exceptional! (421 reviews)

Generally the rooms were clean. Breakfast offered a wide selection of items including meats, cheeses, salads, and sweets. The eggs were not good and did not offer option for fried/ specially made eggs. Staff was friendly and quick to get you you coffee or anything you wanted. I do feel the the way the rooms are represented on line are a misrepresentation of what the rooms really look like. They are not as modern as you might believe and while the are clean they are not as pristine as represented and are in need of upgrades/renovation. It is a pleasant enough hotel, just was expecting more from a 4 star hotel.

Reviewed on Sep 27, 2025

Villa San Lucchese

￥212,228

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Tokyo (HND) to Florence (FLR)

9.4/10 Exceptional! (330 reviews)

This was our third time staying at Villa San Lucchese, and the first time in about 8 years. It was just as wonderful as we remembered! The staff is extremely friendly and that's what keeps us coming back. The accommodations are extremely comfortable. Thank you for the ac! The breakfast has lots of great options, and the fresh scrambled eggs are delicious. We always enjoy dinner at their restaurant as well. Can't wait until our next visit!

Reviewed on Sep 21, 2025

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Top Romantic Chianti Region Hotels

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

San Gimignano

29 min drive from Antinori nel Chianti Classico

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! (70 reviews)

Couples like: hot tub, fireplace

Amazing Property and Hosts!

"This is my first time staying in Italy and San Gimignano. The listing of the property is accurate and everything was very clean and well maintained. The hosts Gabriel,, and rest of the team are exceptional with quick responses and clear communication. Our party had four adults and three children ..."

Reviewed on Aug 10, 2025

Palazzo Leopoldo Dimora Storica & Spa

Via Roma 33, Radda in Chianti, SI

35 min drive from Antinori nel Chianti Classico

Book a stay at this romantic hotel, featuring a spa and in-room massages. Couples will appreciate the hot tub, al fresco dining, and garden.

9.2/10 Wonderful! (267 reviews)

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

Travelers say...

"Front desk staff seemed overwhelmed and were not eager to help. Jacuzzi’s were co"

Reviewed on Sep 13, 2025

COMO Castello Del Nero

Strada Spicciano 7, Barberino Tavarnelle, FI

10 min drive from Antinori nel Chianti Classico

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 ...

9.4/10 Exceptional! (128 reviews)

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

Travelers say...

"Beautiful!"

Reviewed on Aug 2, 2025

See all 5,120 properties in Chianti Region

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.