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Historical

50+ CoolStays.

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  • Sleeps: 2 + 2
  • Bedrooms: 1+ box bed pullout

"A medieval fairytale tower, set near a 14th century castle in the Scottish Borders"

Live Calendar
  • Sleeps: 2
  • Bedrooms: 1

"A chic mill conversion in the magnificent Scottish Borders…"

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

"Romantic retreat combining traditional features with modern luxury in the historic village of High Bickington."

Live Calendar
  • Sleeps: 7
  • Bedrooms: 3

"A traditionally styled stone trullo in beautiful gardens with pool and sun terrace - it’s all you could wish for in a luxury Italian villa"

Live Calendar
  • Sleeps: 4-8
  • Bedrooms: 4

"Two beautifully secluded cottages in the Sussex countryside in 5 acres of gardens and a heated outdoor pool"

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3
 (1 review)

"Luxurious, romantic residence with private four-season pool, spa and wine cellar perched on cliff with a majestic view of a fertile Umbrian valley."

Live Calendar
  • Sleeps: 12
  • Bedrooms: 5

"Combine history and luxury at Great Tangley Manor, a manor house on the edge of the Surrey Hills that dates back 1000 years."

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

"A 19th century coach house in Dartmoor’s wild, untouched scenery, just a short stroll away from the quaint village of Lustleigh"

Live Calendar
  • Sleeps: 8
  • Bedrooms: 4

"Vaulted ceilings and galleried living areas await in this carefully converted former chapel, nestled on the edge of the Exe Estuary"

Live Calendar
  • Boutique Hotel with 20 rooms.

"A simply stunning Burgundy hotel set in a 12th-century abbey with exquisite Michelin-starred food, sumptuous bedrooms with whirlpool baths and acres of private parkland."

  • Sleeps: 17
  • Bedrooms: 5

"A historical property refurbished to the highest standards, surrounded by a delightful Catalonian vineyard and just a short drive from some of Spain’s finest beaches"

Live Calendar
  • Sleeps: 10
  • Bedrooms: 4

"An amazing refurbished antique watermill built into the face of the Catalan mountains and looking out onto a stunning waterfall."

Live Calendar
  • Sleeps: 2-5 each property
  • Bedrooms: 1-2 per property
Multiple Units Available

"Five luxury, holiday rentals in a pretty, rural Finca, where you can explore beautiful Lanzarote and its stunning landscapes…"

Live Calendar
  • Sleeps: 2 + 2
  • Bedrooms: 1

"A spacious studio concealed within this meticulously converted church near Bath"

Live Calendar
  • Sleeps: 8
  • Bedrooms: 4

"Historical beauty meets modern luxury at Ermita del Carmen, a fully refurbished 15th Century chapel located in the heart of Andalusia and surrounded by a natural park."

Live Calendar
  • Sleeps: 16
  • Bedrooms: 7

"Grade II listed 16th Century building in the stunning surroundings of North Yorkshire"

Live Calendar
  • Sleeps: 10
  • Bedrooms: 5
 (4 reviews)

"A stunning and unique five bedroom watermill conversion near Chester"

Live Calendar
  • Sleeps: 12
  • Bedrooms: 4

"A Grade II listed Victorian church combining history and luxury to create the perfect Berkshire retreat for big groups."

Live Calendar
  • Sleeps: 12
  • Bedrooms: 4

"There may be no cash in the vault today, but the Bank Haus is a 1800s Missouri bank building restored to its former glory"

Live Calendar
  • Boutique Hotel with 30 rooms.

"Cowley Manor - A country house hotel fused with award-winning contemporary design and architecture hidden in a secluded Cotswold valley."

  • Sleeps: 6
  • Bedrooms: 3

"Delightful 1670’s renovated cottage in the heart of the beautiful Cotswolds - seriously sleek design with eco credentials too."

Live Calendar
  • Sleeps: 2
  • Bedrooms: 1

"Step away from the hustle and bustle and into traditional English village life at the Wheelwrights, a listed barn dating back to 1870 located in the Essex village of Little Waltham"

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

"Explore the city of venice on foot or on the water before relaxing in your decadent, comfortable, and stylish Venetian apartment."

Live Calendar
  • Sleeps: 4
  • Bedrooms: 1

"Gorgeous apartment in the heart of Venice with it’s own pretty roof terrace offering wonderful views of the city - the perfect spot for a morning coffee."

Live Calendar
  • Sleeps: 14
  • Bedrooms: 8

"Lovingly restored 11th century church and 18th century farmhouse set in rich Umbrian countryside"

Live Calendar
  • Sleeps: 2
  • Bedrooms: 1

"Remarkable 700 year old historic gatehouse lovingly restored as a couples bolthole - Cosy up by the fire or venture out and explore the beautiful Wye Valley."

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3

"The 15th and 21st centuries meet in a modern apartment within a historic gothic palace. Explore Venice from a location in the heart of the city."

Live Calendar
  • Sleeps: 4
  • Bedrooms: 2

"Tranquil, converted Grade II listed building mere moments from a quiet, secluded cove in Pembrokeshire"

Live Calendar
  • Sleeps: 8
  • Bedrooms: 4

"Cool, quirky and oh-so retro, this converted tabernacle church is the perfect one-of-a-kind base for your next sojourn to the beautiful Isle of Wight"

  • Sleeps: 4
  • Bedrooms: 2

"Escape to Bannatyne Cottage, a former lock-keeper's dwelling on Scotland's Crinan Canal."

  • Sleeps: 2
  • Bedrooms: 1

"A lovingly restored boathouse offering a luxurious and relaxing Scottish getaway"

  • Sleeps: 4
  • Bedrooms: 2

"Take a trip back into the past in this Elizabethan gatehouse. Expect plenty of Tudor features, alongside the modern conveniences you need for that perfect getaway..."

Live Calendar
  • Sleeps: 10
  • Bedrooms: 5

"An intimate, historic and beautiful tower, looking out over stunning Scottish landscapes; homely inside, with vast countryside outdoors to discover."

Live Calendar
  • Sleeps: 48
  • Bedrooms: 8

"Get your camp on with a rough and ready stay at this old-school summer campsite in Wisconsin, USA."

  • Sleeps: 9
  • Bedrooms: 3

"Gorgeous triple-cone trullo in the heart of Puglia, Southern Italy - designer style, rustic character, true relaxation"

Live Calendar
  • Boutique Hotel with 2 rooms.

"A chic, boutique hotel with five designer suites; overlooking the ancient island of Folegandros and its sparkling blue sea."

  • Boutique Hotel with 23 rooms.

"Former monastery converted into a five-star boutique hotel & spa, close to Pollensa old town and some of the best beaches on the island."

  • Sleeps: 2-4
  • Bedrooms: 1

"A collection of beautiful Gypsy caravans, each blessed with their own unique beauty and charm, and an alluring cottage, complete with its own Romany caravan"

  • Sleeps: 12
  • Bedrooms: 6

"Take it easy in Ibiza at this charming and historic finca, nestled into the hills of San Antonio, and boasting a large sun terrace and pool."

  • Sleeps: 8
  • Bedrooms: 4

"17th century mansion in the Italian Lakes, recently renovated to inject luxury and technology while maintaining all the period architectural details, with stunning results."

Live Calendar
  • Boutique Hotel with 33 rooms.

"With 37 beautiful rooms overlooking olive groves and vineyards, beautifully restored Crillon le Brave occupies 8 buildings at the foot of Mont Ventoux, just 25 miles from Avignon"

  • Boutique Hotel with 48 rooms.

"A traditional Berkshire village coaching inn reimagined - with designer styling and AA Rosette-winning dining"

  • Boutique Hotel with 18 rooms.

"Beautifully styled boutique hotel right on Venice’s grand canal - live an opulent Art Deco lifestyle within minutes of the sights"

  • Sleeps: 6
  • Bedrooms: 3

"An award winning converted stable in Brooklyn. Unique and gorgeous, this perfect retreat for those who want to experience New York City, but want to stay in a quiet sanctuary."

  • Sleeps: 6
  • Bedrooms: 3

"Cosy stone cottage built by Brunel himself situated in a unique location next to the West Somerset Steam Railway. Enjoy the steam trains from the garden hot tub"

Live Calendar
  • Sleeps: 18
  • Bedrooms: 5

"A beautifully renovated 350 year old former farm building that oozes character and style whilst enjoying the most breathtaking views of Mont Blanc"

Live Calendar
  • Sleeps: 14
  • Bedrooms: 7

"Incredible seafront castle on the Croatian island of Šolta, with 6 super-luxurious suites, pool, saunas, a restaurant and more"

Live Calendar
  • Sleeps: 6
  • Bedrooms: 3

"Stylish historic cottage near the Lake District that offers the ideal location for an active rural escape"

Live Calendar
  • Sleeps: 30
  • Bedrooms: 13

"Georgian house and cottages situated just off the Ring of Kerry, accommodating up to 30 people."

Live Calendar
  • Sleeps: 8
  • Bedrooms: 4

"Enjoy tranquillity, privacy, peace, solitude and location at Smiths Castle - An authentic 15th century Irish castle with a fascinating history, overlooking a river valley on the west coast of Ireland."

Live Calendar
50+ CoolStays. Please use the filters to narrow your search.
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