Stellino

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Entertainment

Bathtub

Hair Dryer

Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Freezer

Fridge

High Chair

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Kitchen & Dining

Cot / Crib

Washing Machine

Bedroom & Laundry

Private Pool

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Heating & Cooling

Private Parking

Free Parking

Parking Available

Parking & Access

Barbeque

Beach / Pool Towels

Fenced Property

Garden

Garden Games

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

Child Friendly

Other

This villa strikes the perfect balance between contemporary and traditional. The terracotta ceilings and floors are original features, but the kitchen and lounge on each level are totally modern – not to mention convenient for larger groups. But it's the sprawling garden that captured our attention. A private swimming pool is a lovely addition during the summer, a separate outbuilding has table tennis and darts, and several seating areas offer spots to relax with a glass of wine – our favourite being the courtyard, ideal for alfresco dining. The nearest village is San Gusmè, but most shops and eateries are in Castelnuovo Berardenga (6 kilometres away). For day trips, head to Siena – just thirty-five minutes by car.

Siena Ceremony

DVD Player

Satellite / Cable TV

Ping Pong Table

Pod Coffee Machine

Toaster

Iron

Ironing Board

Hangers

Laptop Friendly Workspace

Air Conditioning

Central Heating

Free Parking On Premises

Self Check-in / Check-out

Private Entrance

Balcony

This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region. Back at the home, you’ll find everything you need for the quintessential Tuscan trip, with a glimmering pool overlooking the rolling hills, plenty of seating areas dotted around the lush green gardens and a sun-kissed patio, plus enough space to make sure a large group can sprawl out and unwind. Set across two buildings, both interiors exude rustic charm with beamed ceilings and stone archways. Furnished with plenty of Italian passion, there are comfy sofas, a huge dining table and an authentic kitchen. Fire up the barbecue and wait for the meat to grill while indulging in a sundown aperitivo, then dine alfresco long into those balmy summer evenings.

Rolling In Olives

Kettle

Dryer

Hot Tub

This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. 

Sunlight Symphony

Smart TV

Toiletries

Blender

Cleaning Products

Extra Pillows and Blankets

Desk

Welcome Hamper

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms. Sure, the design is traditional, but extras like the welcome hamper and bottle of local wine make it easy to settle in. Out in the landscaped garden, you can splash in the private pool or find a spot to enjoy an alfresco aperitif. Your host can also arrange top-notch services to elevate your stay, from daily housekeeping to guided tours and cooking lessons.

Tuscan Roses

Outdoor Pool

Shared Pool

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all. The private terrace is just the place for an alfresco family meal, while the communal pool promises some respite from the heat. Locally, we recommend a trip to Brolio Castle. This charming estate serves up a wine-tasting room, castle, and restaurant serving authentic Tuscan food – there’s something for everyone here. 

The Tuscan Hills

Board Games

DVD Library

Library of Books

Sound System

Bathrobes

Black-Out Blinds

Drying Rack

Exercise Equipment

Fireplace

Stair Gates

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surrounding countryside. The medieval village of San Gusmè is a mere five-minute drive away, while Siena is a 30-minute trip from your villa, in case you want to do some shopping or sightseeing. Your host provides a complimentary concierge service, too, so that all your holiday whims will be taken care of. Before long, you'll feel like a local.

Chianti Kisses

Heated Towel Rail

Rain Shower

Juicer

Jacuzzi

If this characterful apartment set in an intimate agritourism complex doesn't say Tuscany, we don't know what else will. Surrounded by hectares of olive groves, the home's secluded setting is idyllic. But you're never far from the bustle, with the wander-worthy streets of Siena and countless medieval walled towns all just a short drive away. Inside, the traditional interiors are perfectly in tune with the heritage of this 15th-century farmhouse estate comprised of just five charming apartments. While the indoor living space is limited, the sheltered private terrace and Jacuzzi (for an additional fee) with views of the Tuscan hills are a delight. And wait until you see the shared swimming pool and vast communal lawns at the heart of it all.

Tuscan Hideaway

Set in hectare upon hectare of olive groves and yet just a short drive from the wander-worthy streets of Siena and countless medieval walled towns, the setting of this Tuscan farmhouse apartment is postcard-perfect. A wonderful retreat for two, a single traveller, or a small family, you'll have a private terrace with a barbecue and Jacuzzi (for an additional fee) to soak up the rolling hill vistas, and just across the communal lawns, a shared swimming pool to beat the Tuscan heat. While the traditional interiors might not be everyone's cup of tea, the historic features of this 15th-century estate are impressive.

A Visit from Siena

Parking On Street

Amidst the rolling hills and long stretches of vineyards, you'll be captivated by the peace and serenity of this place from the moment you arrive. Stone clad brickwork and cobbled paths set the scene with a backdrop of the surrounding countryside – painting a picture-perfect view of blissful Tuscan serenity. Inside exposed wooden beams and traditional tiled flooring bring charm to the otherwise modern interiors, and you'll have the choice of eating alfresco or at cooler temperatures from the indoor dining area, when it comes to meal times. Take a dip in the outdoor shared pool, or embark on the day's adventures in and around Tuscany. With golfing, horseback riding, cycle paths and walking trails on offer, if you're the. outdoorsy type – this is the place for you. After a day of exploring feel rest assured in knowing that the bubbling jacuzzi awaits your return – but don't forget to pour yourself a glass of wine before getting in. 

Tuscan Serenity

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities.  Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the evening you can savour wine and antipasti on the veranda or under the vine-wrapped pergola. If you get the itch to explore, a thirty-minute drive will take you to Siena where you can enjoy dining, shopping and sightseeing. 

The Vine Song

Balcony / Patio

Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas. You're in good company here with a castle estate just 2.5km away offering tours, wine tasting and fine dining. Beyond that, the Chianti towns of Gaiole (8.5km) and Castelnuovo Berardenga (11.5km) are an afternoon well spent. Or plan a day trip to Siena, a scenic 20km drive away.

Chianti Hills

Sonos

Baby Bath

Luxury Toiletries

Espresso Machine

Ice Machine

Laundry Supplies

Vacuum Cleaner

Electricity Adaptors

Fenced Garden

Herb Garden

Umbrellas

Smoke Detector

Just driving up to this fabulous Tuscan home is a pleasure in itself. Surrounded by manicured lawns, tall cypress trees and rolling hills, it's an imposing place in a secluded setting. Within the private estate of Arceno, it comprises a main stone-built villa and an Annesso – a historic barn converted into a separate intimate home. The main house is dominated by its central courtyard, while the lush gardens are home to a stunning pool and outdoor dining spots. We love the thought of gathering the whole gang around the long dining tables for lazy lunches of lemon ravioli and chilled white wine, lasting far into the afternoon. Inside, this home is elegant and comfortable, with period features, antique furniture and grand reception rooms. The concierge service makes things even easier, providing items ranging from the basic (oil and selected toiletries) to the delectable (spirits and house wine). One of the best ways to acquaint yourself with the landscape is to book a horse riding session, but if that doesn’t appeal, a walk out into the countryside is just as charming. For the more energetic among us, day trips to Florence and the region’s major towns are possible. 

Botticelli's Primavera

Sauna

EV Charger

Escape to the beautiful Tuscan countryside, with a stay in this traditional Italian home. You’ll be welcomed by a serene garden with a pool and a covered veranda with an outdoor kitchen for alfresco dining. There’s also a wellness area with a sauna and a hot tub to ensure optimum relaxation. Inside, you’ll find tradition and contemporary comfort with all five bedrooms featuring en-site bathrooms for privacy. We recommend hiring a car to get around here, but it’s just a short drive to Ambra where you’ll find the nearest restaurants and shops. You can also drive to Arezzo, Florence and Siena for inspiring day trips.  


Peaceful Love 

Nestled between Siena and Arezzo, this villa ticks all of our boxes for a memorable stay in the heart of Tuscany. The abode is made up of a main house and a separate residence with a living area, kitchenette and en-suite bedroom (ideal for those who like their privacy), so there’s plenty of space for the group to spread out. Not only are there luxury additions like a sauna, pizza oven and swimming pool, but your host also provides a complimentary wine experience and dinner on your first night to make your time here that extra bit special.

Treasure in Tuscany

You could never tire of the rolling hill vistas seen from the private terrace of this pet-friendly Chianti apartment. Set in a handsome farmhouse dating to the 15th century, the home has been reimagined into five independent apartments with a shared swimming pool surrounded by hectares of olive groves at its heart. Inside, while the traditional interiors are charming, the living space with one sofa may feel tight if four of you are sharing. But with a private sun-kissed veranda and Jacuzzi (for an additional fee) outside, we don’t think you’ll mind. Location-wise, take your pick from medieval walled towns or wander-worthy Siena – it’s all just a short journey away.

Olive Green

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. 

Tuscan Flower

Lift Access

Amidst the rolling hills and vineyards of Chianti, this home is perfectly positioned for an idyllic Italian escape. Set within a private estate which includes a vineyard, olive groves and a church, you’ll find everything you could need for a relaxing retreat or special celebration. There’s also a private pool, a gym and an independent barn for two guests – ideal for those seeking a little extra privacy. Daily housekeeping can be organised along with a range of extra services such as a private chef and guided tours. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Castagnoli and San Gusme.

The Sunlight Hideaway

Shared Washing Machine

Fenced Pool

Safe

Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, shared laundry room, and walking trails through the nearby vineyards. The design is definitely traditional, but we're fond of the rustic character – in fact, anything more contemporary would feel out of place in this storybook setting. Speaking of location, pack comfortable shoes. Not only is the apartment set over two levels, but the hilly environment means you'll do lots of climbing. A car is also a must since villages like Gaiole, Radda, and Castelnuovo Beredenga are within driving distance.

Vino on the Terrace

Escape to the Tuscan countryside and experience the charm of this beautiful home, a lovingly restored 19th-century barn perched atop a hill. Surrounded by breathtaking views of the valley, Monte Amiata, and Monte Cetona, this eco-friendly retreat promises a tranquil haven for couples or families seeking a break from the hustle and bustle of daily life. Sure, at full occupancy, two people will sleep on the sofa bed in the living area, but it’s no hardship in this chic, contemporary home. Location-wise, you can hike, bike, visit mediaeval castles or take wine tours – there’s something for everyone here. 

The Charm of Tuscany

This studio apartment in a stone barn conversion is a perfect blend of modern and antique design. We love the infinity pool (40 metres away) which overlooks the Val d'Orcia, offering breathtaking views. It’s surrounded by wild plants and shrubs that reflect the forested land beyond. The owner’s live in the main house with their two friendly dogs and they occasionally use the pool when the area is unattended by guests. The private furnished terrace and outdoor lounge area here is a lovely spot for a glass of wine. If you prefer to be a bit more active, there are endless trails and routes for walkers and bikers, while the pretty village of Gaiole is 11 kilometres away.

The Chianti Cottage

Steam Room

Parking On Premises

Nestled in the heart of the Chianti Classico region, this restored Tuscan farmhouse promises an idyllic escape. Sure, the traditional interiors may not be to everyone’s taste, but this home has all the key ingredients for a relaxing stay. And the cherry on the cake for us is the outdoor space. A private pool, hot tub, sun-drenched terraces and views for miles – what’s not to love? Location-wise, it’s a short 5km drive to Gaiole, where authentic Tuscan eateries and wine tasting await.

Tuscan Gaze

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. 

Chianti Glow

Tennis Court

Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure.

Tuscan Flow

Sauna / Steam Room

Amid the rolling hills and verdant countryside of Tuscany, this home delivers rustic Italian charm and idyllic views. Inside, the rooms unfold across three floors in the main house and two floors in the adjoining annexe – providing an abundance of space and a wonderful sense of character. Outside, the garden lends itself perfectly to lazy days by the pool (open seasonally) and long soaks in the heated jacuzzi. You will need a car to get around here, but it's just 6 kilometres to the nearby town of Ambra (don’t miss the weekly market), plus it’s also within easy reach of Siena, Arezzo, and Cortona.  

Lavender & Lemons

Bicycles

Desk / Workplace

Outdoor Shower

This is an excellent base from which to explore Tuscany and Chianti. The stone villa is a classic example of Tuscan style, which has been renovated into a comfortable home – it has everything you might need and is still full of authentic charm. 

You’ll wake up under an authentic wood-beamed ceiling in one of the elegant bedrooms. Making your way downstairs, past antique paintings and a grandfather clock, you’ll enter the dining and living space. As in any Italian home, this is the heart – you’ll likely spend hours sitting around the dining table.

Outside, the covered veranda is the perfect place to sip coffee – or vino in the afternoon. The pool is a short stroll away, surrounded by lush lawns and trees. It’s a dreamy place to be whether you’re swimming laps, soaking up the sun by the water, or reading a book in the Jacuzzi. 

The villa is a twenty-nine-minute drive from Siena, which is a great city for day trips. Discover the history of the Palio, enjoy a spot of shopping, and treat yourselves to a decadent lunch in a piazza. 


Sipping Chianti

With stunning views of the valley, this ground-floor apartment in this countryside resort has its own outdoor dining area where you may spot passing deer and other animals. There’s a shared swimming pool, a short stroll away too (though there are numerous wooden steps down to it). Inside this home, the décor is quite traditional and simple, but with so much on offer in the area, will you actually spend much time indoors? The resort boasts 10 kilometres of marked trails for hiking through the woods and vineyards of Fietri, while the pretty towns of Castelnuovo Beredenga and Gaiole are both 15km away via winding roads. 

The Chianti Garden

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

Cafetiere

Wine Cellar

Pool House

Outdoor Fireplace / Firepit

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away.

That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. 

Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved lines of the kitchen – it’s perfect for entertaining your family and friends. Upstairs, the bedrooms have glorious countryside vistas, four posters and beds with beautiful landscapes painted on them. The master has a whirlpool tub, too, if you want to have a luxurious soak.

If you fancy exploring the area – Siena is a twenty-minute drive away with its splendid Palazzo Pubblico and Torre del Mangia, a slender 14th-century tower. 


Beneath The Autumnal Sun

Private Washing Machine

The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play. More active guests can explore the sweeping grounds, play table tennis in the second living area, or cool off in the shared pool. Meanwhile, those seeking tranquillity can settle on a sun lounger, dine out on the terrace, or refine their cooking in the eye-catching wooden kitchen. The historic city of Siena lies 10km away, where the hectic Il Palio horse race turns the streets into a bustling festival twice a summer.

Siena Charm

Nestled among the olive groves of Chianti, this home welcomes you to enjoy mesmerising views and ultimate relaxation. There’s a private pool and a perfectly positioned terrace for sunset drinks and alfresco dining. Inside, the rooms are traditional, simple and well suited to families. You’ll also find one of the bedrooms is located in the pool house – providing a sweet and private sanctuary for two guests. You will need a car to get around here, but it’s just a short drive to the nearest amenities, while the beautiful Castelnuovo Berardenga (renowned for its delicious wine, restaurants and castles) is also just a short drive away. 

Celebrate the Moment

Set in the picturesque village of San Sano, this home offers the best of both worlds – easy access to amenities and a quiet space to retreat to and relax. You won’t tire of the vineyard views here. Best enjoyed, we think, over a bottle of Chianti on the terrace or from the private pool. You’ll also find a lovely alfresco dining spot, though it’s a mere one-minute walk to the nearest restaurant, so eating out is sure to be on the menu. And when you’re keen to venture further afield, a trip to Siena is a must. 

Chianti Dream

Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills. Start your day with a friendly tennis match on the communal courts, and unwind poolside post-match. With no air-conditioning, it may feel a little warm during the summer months, but there are plenty of shaded spots when you need respite. Embark on cultural escapades to Siena, or hike the Dievole Natural Path, winding up at a winery, where you can enjoy a tasting at the cellar's restaurant.

Tuscany Magic

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be to everyone's taste, but it's certainly not lacking in charm. Opposite the main home, you'll find a stone barn with a kitchen, dining area and second living room, ideal for family dinners. We recommend hiring a car here, with the city of Siena less than an hour's drive away – the road up to the home is unpaved and uneven though, so it won't be suitable for smaller cars.

Olive & Olive Wood

Games Room

Pool / Snooker Table

Heated Pool

Safety Gates

This 400-year-old luxury farmhouse sits in the Chianti hills between Florence and Siena. Up on a hilltop, the view over the forest-clad countryside is simply sublime, from secluded seating nooks around the garden and from the 12-person dining table on the patio. Alfresco dining is a cinch thanks to a wood-fired pizza oven and barbecue area. An infinity pool invites you for a cooling dip and there’s a dedicated games room inside for evenings at the pool table. The group can spread out between two sitting rooms inside where the traditional farmhouse aesthetic blends with modern features. Wine-tasting sessions are on offer in the private wine cellar, arranged through your host.

Chianti Breeze

Gated Community

Single-Level Home

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. 


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