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Sailing holidays (361)

Family sailing holidays aren’t just an opportunity for budding skippers to wear silly hats and control the tiller all holiday long – the plus points are rather more numerous than that. Just think about it: you can set sail whenever you like, sailing from one beautiful location to another at the turn of a wheel. Best of all, you don’t have to put up with heaving beaches. Just find your own deserted stretch of sand or an isolated cove, moor up and enjoy the sunshine and quiet. Sailing doesn’t have to be an activity holiday, you know.

The more competent sailors among you might like to take the wheel yourself on one of our yachts in Spain or Greece. Or, for a little added luxury, you can hire your own private skipper.

For families in which there’s an even split between sea legs and landlubbers, there’s the sailing holiday compromise of renting a holiday home that has the use of its own boat and private mooring. Check out these sailing adventures in the Caribbean and along the coast of England.

But if sailing sounds just a little too involving for what’s supposed to be a relaxing holiday, there is the more tranquil option of a houseboat. Either stay put or pootle merrily around the waterways of England and the Netherlands. Whichever appeals more, you should definitely step aboard soon.

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361 Results  |  
20 Photos

Houseboat | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £91 /night

£631 - £999 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
  • Private garden
Authentic houseboat perfect for couples and friends . Situated in a green street, no noise at nigh, close to the hart of the city center.  …see more

9 Photos

Yacht | 5 Bedrooms | sleeps 9

1 night min stay

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from £43 /night

£297 - £2152 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
a short walk from the airport turn right into marina cross the golden bridge directly to the Jasmine and next to the Jasmine can be found the famous dolphin adventure school great experience for all ages or trek to the top of monkey rock  …see more

14 Photos

Yacht | 2 Bedrooms | sleeps 6

1 night min stay

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from £485 /night

£3392 - £4452 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • Air conditioning
  • No pets allowed
Luxury Motor yacht based in Fiskardo. Kefalonia. The perfect way to explore Ithaca, Lefkas, Scorpios and the many islands in the Ionian Sea. Greece.  …see more

Featured properties

13 Photos

Houseboat | 6 Bedrooms | sleeps 18

1 night min stay

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from £91 /night

£631 - £833 / week

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Key info:

  • Nearest beach 30 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Traditional Sailing Clipper houseboat, moored in the centre of the city of Groningen. To be rented as bed and breakfast or to be rented as total ship.  …see more

18 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £243 /night

£1696 - £2120 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Enhance your holiday experience by visiting Zakynthos, Ithaca, Kefalonia, Lefkada, Scorpios and Meganisi on a professionally maintained 38 ft sailing yacht with a fully qualified Skipper. Breakfast and lunches included in the price with no added extras. Enjoy the beautiful scenery around the Ionian Islands. You are guaranteed to have a special holiday.  …see more

24 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £742 /night

£5194 / week

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Late Deal: save up to £1400

Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
We offer a flavour of our most popular itineraries, which you can undertake on our exclusive yacht charter in Kas, Turkey, but every facet of the trip is up for discussion. We want to offer you the holiday of a lifetime, taking in the sites that you've always dreamed.  …see more

15 Photos

Yacht | 2 Bedrooms | sleeps 5

Short stays welcome

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from £87 /night

£605 - £2418 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Mediterranean Sea, Sailing, Charter, accomodation, full procisioning, relaxing, beaches  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 3

3 Nights min stay

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from £36 /night

£246 - £1159 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Sailing holidays in France, Italy,Corsica and Sardinia aboard a skippered yacht. A chance to just relax or learn to sail. Where else but on a yacht can you wake in a morning, sail and relax to lunch in a beautiful bay, then sail again for a new port, marina or anchorage Check out our 2011 season on YouTube. http://www.youtube.com/watch?v=uxoZjnFiA58  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £101 /night

£701 - £3417 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Yacht charter, Eolie islands, Aeolian islands, Auracharter  …see more

24 Photos

Yacht | 3 Bedrooms | sleeps 6

1 night min stay

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from £526 /night

£3680 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Villa Rental, Holiday in a Hotel…none comes close to the experience of travel by BOAT! Let's explore why: Firstly, you can comfortably move around, lie down, or sit at a table whilst your vessel glides along the sea. You are surrounded by ever changing natural beauty. You should keep in mind a boat tour for your holiday vacation.  …see more

6 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £99 /night

£689 - £1007 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Lucy Joe Sleeps upto 4 - Wheelchair access available A beautifully finished boat, Lucy Joe has been designed with space, luxury and comfort in mind. Stay onboard at our marina as an alternative to an hotel or explore the waterways. A warm welcome awaits.  …see more

24 Photos

Yacht | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

1 night min stay

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from £265 /night

£1855 - £2120 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
S/Y Ann Sofi Bavaria 44 based in Didim Marina, south west Turkey. Well equipped available to charter bareboat or skippered. 3 double cabins, master suite with shower room. Roomy cockpit. All safety and navigation equipment provided. 5 star luxury marina base Sail the Turkish coast and the Greek Dodacanese islands on a luxury yacht.  …see more

15 Photos

Yacht | 2 Bedrooms | sleeps 6

1 night min stay

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from £263 /night

£1840 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
The Bachelor is an impressive 58ft STRIKER, equipped with all the amenities and luxury's of a Yacht, with one Master bedroom and on guest bedroom, in addition to a sofa bed this can accommodate up to six people onboard, one of the great pleasures is sleeping onboard. Overnighting is a wonderful way to spend an evening, sleeping on the hook!  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 4

7 Nights min stay

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from £73 /night

£509 - £2460 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Sailing Yacht. Typically start/finish Corfu, visit Sivota Mourtas, Parga, Arillas, Paxos and Anti Paxos Go with our itinerary or set your own, take part in the sailing as much or as little as you like....  …see more

16 Photos

Narrowboat | 1 Bedroom | sleeps 6

3 Nights min stay

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from £75 /night

£520 - £742 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
The Royal Canal has a mysterious element and is unique in the amount of towns small and big that it passes through on its way from Dublin to the Shannon. There is a local canal society in each town who work hard to keep the canal clean and welcoming to you.  …see more

16 Photos

Yacht | 2 Bedrooms | sleeps 12

1 night min stay

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from £351 /night

£2453 - £2891 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Yacht rent Portoroz Slovenia Croatia Venice Italy  …see more

22 Photos

Yacht | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £46 /night

£316 - £684 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • Pets welcome
It is almost impossible to talk about Lanzarote without a reference to the sea. To enjoy a unique experience staying onboard a sailing yacht slightly and sweetly rocked by the sea is something that we will remember our entire life. Enjoy a different holiday! We are LGBT friendly and proud of it. Pets are welcome, sheltered place on deck will be provided.  …see more

8 Photos

Houseboat | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £564 /night

£3943 - £5520 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
COMFORT auxiliary dinghy with outboard motor boat lifts hot water external shower light mattresses in bathtub bathroom steps bimini shades in control area bathtub with rigid bimini shade three fridges (one outdoors) kitchen and oven CD MP3 speakers in bathroo  …see more

21 Photos

Yacht | 3 Bedrooms | sleeps 8

1 night min stay

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from £276 /night

£1928 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
FULLY UKOMPLETOVAN, ready for any SEA TRAVEL or holidays in 5 ANCHOR YACHT MARINAS. This is better than 5 STARS hotels Experienced skipper will make your vacation fun and safe  …see more

14 Photos

Yacht | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £64 /night

£446 - £557 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Luxury yacht situated in Queensway Quay Marina.  …see more

15 Photos

Narrowboat | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £144 /night

£1007 - £1299 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
boat, hideaway,nature,meditation,romantic getaway,special occasions ,different Canal Boat, 2 bedroom on the Rickmansworth canal, Hertfordshire, 30 min drive from Central London, there is  …see more

18 Photos

Yacht | 5 Bedrooms | sleeps 7

Excellent 5/5 

2 Nights min stay

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from £439 /night

£3067 - £3505 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Private Sailing Holidays in Greece and Turkey with Gourmet Chef - 2 professional crew (40+ years experienced Italian-Greek captain + hostess/co-skipper) Captain - with a remarkable past in the vest of a professional super yachts captain of over 60,000 NM in his  …see more

19 Photos

Yacht | 4 Bedrooms | sleeps 8

1 night min stay

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from £501 /night

£3505 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Thousands of foreigner and local people visit this little town of Mediterranean, the capital of light, Kas. Kas draw attention with its history, blue and clean sea and fascinating nature. Many different tour opportunities will be waiting for you during you Kas travel  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £126 /night

£877 - £1534 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
yacht from owner, afordable, luxury, comfortable, sailing experience, yacht in GREECE,  …see more

17 Photos

Yacht | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £126 /night

£877 - £1052 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
This ia a yacht with NEW equipment in excellent condition. Sea worthy , comfortable clean including all comfort available from owner at discounted prices through the year.  …see more

12 Photos

Yacht | 4 Bedrooms | sleeps 7

Excellent 5/5 

1 night min stay

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from £238 /night

£1665 - £2453 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
vacations in sailboat 11m max 7 people, among Taranto, I Bring caesarian, Gallipoli, Saint Maria of Leuca, Otranto, Greece  …see more

20 Photos

Narrowboat | 3 Bedrooms | sleeps 6

Short stays welcome

Add to shortlist

from £113 /night

£789 - £1052 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Holidays in Paris, unusual lodgings, new experience  …see more

15 Photos

Houseboat | 4 Bedrooms | sleeps 12

Very Good 4.5/5 

1 night min stay

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from £164 /night

£1145 - £1304 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Best and Authentic houseboats at best rates. Book direct from the owner for 2, 3, 4 or 5 bedroom houseboats at alleppey.  …see more

10 Photos

Narrowboat | 1 Bedroom | sleeps 4

3 Nights min stay

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from £120 /night

£838 / week

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Key info:

  • Nearest beach 0.2 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Bluebell Narrowboat Holidays is a family run small business which offers traditional canal boat holidays along 41 miles of lock free cruising on the Lancaster Canal. Come along with family or friends for a quality, slow-paced English getaway. One price all year. Call us to discuss your enquiry 01524 811196 07854 596989  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £280 /night

£1954 - £2846 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Holiday catamaran sailing charter, from Alanya, Antalya, Kemer, Kas, Dalaman, Marmaris, Fethiye, Gocek, Kalkan & Rhodos (GR). Excl.: Diesel, Transit log (Tourist tax), food & Beverage on board, Harbor mooring fees, Personnel travel  …see more

23 Photos

Yacht | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £86 /night

£600 - £914 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Dartmouth yacht stay, self catering holiday, panoramic harbour view, unique holiday  …see more

12 Photos

Houseboat | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

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from £76 /night

£526 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Annie's Boat is a B&B (bed & boat) for a relaxing stay in a vibrant city. Are you looking for a houseboat situated in a quiet area, yet close to the hustle and bustle of the city? Then Annie's Boat is the place to be! smoking is only allowed outside  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £211 /night

£1474 - £2624 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Neverland is a 47ft luxury Moody Sailing Yacht, in pristine condition built in 2002 available for skippered charter. She can accommodate up to 5 guests. Breakfast light lunch, tea and coffee are included in the price. Cold drinks apart from water are chargeable. Yacht charter from Olbia Free skipper and hostess. Free breakfast, light lunch, tea coffee.  …see more

4 Photos

Houseboat | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £145 /night

£1012 - £1644 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
No license needed, easy to maoeuvre, cruises in the lagoon of Venice.  …see more

9 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £570 /night

£3986 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Touaou est un catamaran sûr et coinfortable, il a traversé les océans et son capitaine a exercé préalablement dans la Marine pendant 30 ans comme officier de manoeuvre, de navigation puis comme commandant. Touaou est idéal pour 3 couples ou pour une famille.  …see more

7 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Short stays welcome

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from £92 /night

£639 - £1072 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

13 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £117 /night

£815 - £1382 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

8 Photos

Narrowboat | 1 Bedroom | sleeps 3

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £73 /night

£510 - £848 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

15 Photos

Narrowboat | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £92 /night

£639 - £1072 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
We are ideally situated for Wedgeood, Trentham Monkey Park , the Potteries, Alton Towers and Drayton Mannor Park. We are on the Four Counties Ring on the Trent and Mersy Canal from which you can vist Wales, Cheshire, Shropshire and Staffordshire.  …see more

7 Photos

Narrowboat | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £138 /night

£965 - £1492 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

21 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £92 /night

£639 - £1072 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

20 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £117 /night

£815 - £1382 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Based on the trent and mersey canal Ideal starting point for a different type of holiday  …see more

13 Photos

Narrowboat | 1 Bedroom | sleeps 3

Excellent 5/5 

3 Nights min stay

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from £73 /night

£510 - £848 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

9 Photos

Narrowboat | 4 Bedrooms | sleeps 8

Short stays welcome

Add to shortlist

from £164 /night

£1142 - £1872 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire. http://www.youtube.com/watch?v=ic_XjbO_tZA  …see more

16 Photos

Narrowboat | 1 Bedroom | sleeps 3

Short stays welcome

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from £96 /night

£670 - £977 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
we are ideally situated for the Wedgwood factory, Trentham Monkey Park, Shugborough, Alton Towers and Drayton Manor Park. We are on the Four Counties Ring on the Trent and Mersey Canal, The Cauldon is just a short distance away from us. a beautiful canal.  …see more

12 Photos

Narrowboat | 1 Bedroom | sleeps 3

3 Nights min stay

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from £95 /night

£659 - £959 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

13 Photos

Narrowboat | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £96 /night

£670 - £977 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

9 Photos

Narrowboat | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £164 /night

£1142 - £1872 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

6 Photos

Narrowboat | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £138 /night

£965 - £1492 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Situated in the heart of England, it the ideal starting point for a different type of Holiday. From Stone you have several choices of routes i.e., an energetic Week The Four Counties Ring or a quieter week the Caldon and Harecastle Tunnel. Why not a days hire.  …see more

12 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £114 /night

£795 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • Air conditioning
  • No pets allowed
We are a family run business and our boat Vivione111 is a Luxury Yacht moored in the harbour of Duquesa. Costa Del Sol Boat Holidays let you explore this beautiful region of spain and stay in the Luxury of Puerto de la Duquesa, with it's Golf Courses, bars, restaurants.  …see more