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Check availability on Roccastrada Historic Hotels

Our top choices for Roccastrada historic hotels

Interior
The Gelda house, relax with a view

The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is AED 427
AED 606 total
includes taxes & fees
16 Dec - 17 Dec
The Gelda house, relax with a view
Dining
Comfort, relaxation and nature

Comfort, relaxation and nature

Comfort, relaxation and nature
Monticiano
10.0 out of 10, Exceptional, (1)
"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"
Italy
Sandra V.
The price is AED 307
AED 436 total
includes taxes & fees
12 Dec - 13 Dec
Comfort, relaxation and nature
2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"Wonderful stay "
United States
Talib
The price is AED 4,441
AED 4,928 total
includes taxes & fees
4 Jan - 5 January 2026
Castiglion del Bosco, A Rosewood Hotel
Pool
panoramica casa con piscina privata

panoramica casa con piscina privata

panoramica casa con piscina privata
siena
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
The price is AED 346
AED 641 total
includes taxes & fees
23 Dec - 24 Dec
panoramica casa con piscina privata
Fridge, oven, stovetop, coffee/tea maker
Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi

Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi

Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi
Massa Marittima
10.0 out of 10, Exceptional, (3)
"We enjoyed being right in the center of such a lovely town. Enrico was very helpful to us during our stay."
United States
Leslie T.
The price is AED 573
AED 630 total
includes taxes & fees
24 Dec - 25 Dec
Palazzo Malfatti - Appartamento deluxe con vista Piazza Garibaldi
Iron/ironing board, WiFi, bed sheets
Palazzo Malfatti- Studio flat standard

Palazzo Malfatti- Studio flat standard

Palazzo Malfatti- Studio flat standard
Massa Marittima
9.0 out of 10, Wonderful, (2)
"Short walk to the San Cerbone cathedral and the piazza. Great restaurants and shops very close."
United States
John H.
The price is AED 412
AED 454 total
includes taxes & fees
24 Dec - 25 Dec
Palazzo Malfatti- Studio flat standard
Exterior detail
BANDINI 35-central with elevator and air conditioning

BANDINI 35-central with elevator and air conditioning

BANDINI 35-central with elevator and air conditioning
Siena City Centre
9.2 out of 10, Wonderful, (9)
"We loved our stay here. Located on a quiet street but close to Piazza del Campo."
United States
Nancy H.
The price is AED 335
AED 685 total
includes taxes & fees
18 Dec - 19 Dec
BANDINI 35-central with elevator and air conditioning
Fridge, microwave, oven, stovetop
Apartment "Casa Renata" (free covered private parking)

Apartment "Casa Renata" (free covered private parking)

Apartment "Casa Renata" (free covered private parking)
Siena
10.0 out of 10, Exceptional, (1)
"We werden netjes ontvangen door de eigenaar. Hij spreekt goed Engels. Het appartement is heel netjes en ruim met twee badkamerspullen en heeft een goede prijs kwaliteit verhouding. We hebben een prima verblijf gehad. Een ritje naar Siena is maar 6km."
Netherlands
Olav S.
The price is AED 363
AED 819 total
includes taxes & fees
15 Dec - 16 Dec
Apartment "Casa Renata" (free covered private parking)
Indoor pool, a heated pool
Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View
Boccheggiano
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
The price is AED 12,463
AED 14,784 total
includes taxes & fees
31 Dec - 1 January 2026
Private House with Exclusive Swimming Pool Heated and Amazing View
Exterior detail
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is AED 645
AED 872 total
includes taxes & fees
11 Jan - 12 January 2026
The House of Alice, charm and relaxation
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.
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Top Roccastrada Hotel Reviews

Villa del Sole Siena

Villa del Sole Siena

10/10 Excellent
"Amazing rooms and service!!"
Janet 1-night trip
Posted 3 days ago
Villa del Sole Siena

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Frequently asked questions

What can a history buff expect from a stay in Roccastrada?
Significant historical sites in Roccastrada are probably at the top of your travel itinerary. And take some time to enjoy all there is to see and do while you're visiting the area.
What's the best accommodation in Roccastrada to absorb the local history?
Farmhouse apartment between Siena and the sea relax pool WiFi 2 bedrooms 4-5p is one of the top choices for history buffs. A couple of other options near historic sites include Apartment Farmhouse between Siena and the Sea relax swimming pool WiFi 1 room 2-4 P and Apartment Farmhouse between Siena and the sea relax pool WiFi 1 room 2-4p.
How many historical hotels are located in Roccastrada?
In Roccastrada, you'll find 181 hotels and other accommodations bookable on Expedia, including 11 historic hotels or hotels close to historic sites.
What are the must-see historical places and other sights to visit in Roccastrada?
Landmarks like Castello del Belagaio and Sassoforte Castle in Roccastrada might be worth a visit. The picturesque setting of I Canaloni del Torrente Farma and Val di Merse exemplify the area's natural beauty. Additionally, you might want to add Podere Ristella Vineyards and Winery to your agenda.
What is a historic hotel like in Roccastrada?
Guests who book a historic hotel can enjoy a vacation someplace that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of such hotels in Roccastrada, giving a sense of history.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, while "historic hotel" is a term often used in the U.S. but overall the terms are quite similar. The architecture and actual building of a historic hotel is generally the most important aspect. For a heritage hotel, often it's the cultural value and how it inspired the community.
Do historic hotels in Roccastrada have modern facilities?
Yes, every effort is made to preserve the historic aspects and traditions, but interiors include modern conveniences and safety features. Visitors can expect the amenities you'd find in a hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. When you book a historic hotel in Roccastrada, it doesn't mean you're choosing a place that's rundown or uncomfortable for guests.