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Sailing holidays (188)

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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188 Results  |  
15 Photos

Houseboat | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £137 /night

£958 - £1112 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Beautiful house boat in the city centre of Amsterdam. The best place to be in Amsterdam. Living in the middle of the city at the water. It's perfect for couples, friends or a family. It a very nice spot for children and for everybody a complete new experience!  …see more

20 Photos

Houseboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £88 /night

£616 - £1283 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Authentic houseboat perfect for couples and friends . Situated in a green street, no noise at night, close to the hart of the city center.  …see more

24 Photos

Houseboat | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

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from £69 /night

£479 - £556 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Pets welcome
Houseboat, roof terrace, brand new, centre amsterdam, museum square  …see more

Featured properties

19 Photos

Yacht | 4 Bedrooms | sleeps 8

Very Good 4/5 

1 night min stay

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from £611 /night

£4275 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
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

20 Photos

Houseboat | 1 Bedroom | sleeps 4

3 Nights min stay

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from £123 /night

£855 - £1197 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Pantheos Romantic Houseboat Prinsengracht Amsterdam  …see more

21 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £92 /night

£639 - £975 / week

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Key info:

  • Great 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

23 Photos

Narrowboat | 1 Bedroom | sleeps 4

2 Nights min stay

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from £53 /night

£371 - £636 / week

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Late Deal: save up to £320

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
A narrow boat home, Peewit is cruised all year round on the Northampton arm and the Leicester line of the Grand Union Canal. Where you stay will depend from one week to another along this route. All I ask is that you enjoy your stay and leave our narrowboat as you found it, for others to enjoy.  …see more

6 Photos

Yacht | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £129 /night

£901 - £1484 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Sailing Yacht Beneteau Oceanis 393 (3 double cabins and 2 heads) based in the Greek Dodecanese islands available direct from English owner. The prices on this website are for bareboat charters. A skipper is available at approx cost of £110 per day.  …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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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • 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

18 Photos

Houseboat | 1 Bedroom | sleeps 4

2 Nights min stay

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from £135 /night

£941 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Houseboat City centre Amsterdam Houseboat City centre Amsterdam  …see more

16 Photos

Yacht | 3 Bedrooms | sleeps 3

3 Nights min stay

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from £35 /night

£240 - £1131 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Sailing holidays in Corsica and Sardinia aboard a skippered yacht. A chance to just relax or learn to sail. Kayaking and cycling holidays in France in 2015 using our yacht as your mobile base camp. We like to share our lifestyle with like minded people. Please contact us if you have a query.  …see more

20 Photos

Narrowboat | 3 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £22 /night

£149 - £2226 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The perfect place to slow down, get closer to nature and experience the unique British canal system. Offering B&B, day trips, weekend retreats and longer breaks. Join an existing trip or book the whole boat. Home-cooked veggie/vegan food available. Narrow boats, wide eyes, open minds...  …see more

24 Photos

Yacht | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £1245 /night

£8711 - £11476 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Lagoon Catamaran 17 meters long and 10 meters wide, fully furnished and serviced, for maximum comfort in living indoor and outdoor spaces and in the cabins, 3 with double bed and 1 with twin beds.  …see more

12 Photos

Houseboat | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

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from £74 /night

£513 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
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

22 Photos

Yacht | 3 Bedrooms | sleeps 8

2 Nights min stay

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from £184 /night

£1283 - £2138 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
Discover the turkish coast and secret coves by sea. Visit the Greek island of Symi. We offer you our traditional wooden sailing boat Gulet - Trandil (schooner - ketch) to discover the blue voyage and turquoise cruises, pearl of Turkey.  …see more

9 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £556 /night

£3890 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • 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

4 Photos

Houseboat | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £142 /night

£988 - £1347 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Pets welcome
No license needed, easy to maoeuvre, cruises in the lagoon of Venice.  …see more

14 Photos

Yacht | 8 Bedrooms | sleeps 16

Short stays welcome

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from £1496 /night

£10472 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
Private Yacht Blue Cruise, gather your loved ones for a once in a lifetime experience. Explore and enjoy some of the most exclusive cruising grounds in Turkey from the comfort of your own yacht. Tailor made yachting holiday,exclusively made for your requirements.  …see more

12 Photos

Yacht | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £471 /night

£3292 - £4788 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 400 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Gulet cruises are ideal for single travellers and couples alike. It's the perfect opportunity to get to meet fellow backpackers like yourselves. Whether you're an adventurer or more of a loner type of person, this cruise is the best way to discover the beautiful Turkis  …see more

5 Photos

Yacht | 5 Bedrooms | sleeps 10

Short stays welcome

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from £813 /night

£5685 - £8528 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
PRIVATE YACHT, YACHT CHARTER, GULET, MARMARIS, BODRUM, GOCEK, MOTOR YACHT  …see more

17 Photos

Yacht | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £123 /night

£855 - £1026 / week

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Key info:

  • Beach / lakeside relaxation
  • Great 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

16 Photos

Yacht | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £123 /night

£855 - £1496 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
yacht from owner, afordable, luxury, comfortable, sailing experience, yacht in GREECE,  …see more

6 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £106 /night

£737 - £1007 / week

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Key info:

  • Beach / lakeside relaxation
  • Great 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

Houseboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £88 /night

£611 - £1556 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Two luxury, 100% smoke-free rooms on a boat, and en suite bathrooms, free WiFI. After a busy day in the center you can enjoy the grand view of the eastern docklands on the deck terrace on a nice summer's day. Also suitable for 2 quests. Stay on the water in the Venice of the North: Amsterdam.  …see more

10 Photos

Houseboat | 1 Bedroom | sleeps 2

1 night min stay

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from £10 /night

£69 - £446 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The inside of the boats is fully equipped with: One cabin with two single beds, storage space,sofa,kitchen and toilet facilities. The outside exists of: Open lounge deck, Barbecue and Roof top sun.  …see more

24 Photos

Yacht | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £684 /night

£4788 - £7780 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Turkish Ketch Yorgun 1 is a 23m Turkish Gullet built in 2005 and refitted in 2013. Yorgun 1 is in excellent condition and offers comfortable accommodation for 10 guests in 5 cabins, each with a private bathroom, toilet and air-conditioning. Private yacht tour the best part of Mediterranean. Göcek, Marmaris, Fethiye, Datça, Bodrum.  …see more

11 Photos

Houseboat | 4 Bedrooms | sleeps 6

7 Nights min stay

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from £1466 /night

£10259 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
Enjoy a unique cruise experience on the canals and rivers of South West France aboard the Cruisebarge 'easyvie'. Our half-board fare includes comfortable ensuite twin cabins complemented by a spacious lounge and a superb sun deck to watch the world go by.  …see more

4 Photos

Yacht | 3 Bedrooms | sleeps 6

1 night min stay

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from £98 /night

£684 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Annette Rosenkilde is a place of complete tranquility; enjoy the sea breeze, explore the underwater life, relax on deck...the choice is yours! We look forward to welcoming you onboard!  …see more

24 Photos

Yacht | 2 Bedrooms | sleeps 5

1 night min stay

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from £367 /night

£2564 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Bateau MONTECARLO 32 HARD TOP 10m50 2010 conception BENETEAU Bateau FLYER SUNDECK 2010 conception BENETEAU L'Esprit de Famille nous anime, nous saurons répondre à vos attentes!  …see more

15 Photos

Narrowboat | 3 Bedrooms | sleeps 6

Short stays welcome

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from £143 /night

£997 - £1315 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Price Includes: Full boat inventory, all fuel, car parking, bed linen, towels, boating tuition on arrival, pump out tokens, welcome pack including tea towels, washing-up liquid, soap, toilet rolls. Buoyancy aids are available on request.  …see more

10 Photos

Narrowboat | 1 Bedroom | sleeps 3

3 Nights min stay

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from £103 /night

£716 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Narrowboat onthe lock-free Lancaster canal  …see more

12 Photos

Yacht | 4 Bedrooms | sleeps 7

Excellent 5/5 

1 night min stay

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from £233 /night

£1625 - £1967 / week

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Key info:

  • Great 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

18 Photos

Yacht | 5 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £428 /night

£2992 - £4275 / week

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Key info:

  • Beach / lakeside relaxation
  • Great 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

22 Photos

Houseboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £72 /night

£500 - £1344 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Experience a cruise in Kumarakom and Alleppey backwaters while soaking in the breathtaking natural surroundings Kerala has to offer and a personal chef on board offers the best local flavors.All meals provided : welcome drink, lunch,evening snacks,dinner and breakfast. Children under 5 yrs stay free of charge & children over 5 yrs or adult is charged 1400 with extra mattress  …see more

16 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £153 /night

£1065 - £1272 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Luxury Narrowboat holidays in the heart of England which offer a unique and relaxing way of discovering the English countryside and fascinating heritage. Beginners welcome, full training provided. Bed linen, towels, safety and boating equipment and WIFI is included in the holiday cost, fuel is extra.  …see more

16 Photos

Yacht | 2 Bedrooms | sleeps 4

1 night min stay

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from £12 /night

£78 - £175 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
A full equipped sailing boat in the amazing Ancient port of Gaeta  …see more

11 Photos

Houseboat | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £135 /night

£941 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Cruise Ireland's Grand Canal in Co. Kildare on a beautifully restored Canal Narrow-boat. No boating experience is necessary and full barge handling training is provided. Perfect for couples and you can bring the dog! Full self-catering facilities. On Street parking available in Sallins plus train and bus links to Dublin.  …see more

15 Photos

Houseboat | 4 Bedrooms | sleeps 12

Very Good 4.5/5 

1 night min stay

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from £169 /night

£1181 - £1344 / week

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Key info:

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

19 Photos

Yacht | 10 Bedrooms | sleeps 20

1 night min stay

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from £19 /night

£132 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Highlights: - Cruise through stunning Halong Bay on traditional Asian junk - Kayak around breathtaking limestone scenery - Vietnamese feast of delicious seafood - Visiting Sung Sot cave and Ti Top island - Cooking Class - Squid fishing at night  …see more

6 Photos

Houseboat | 26 Bedrooms | sleeps 50

Excellent 5/5 

3 Nights min stay

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from £134 /night

£935 - £42385 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Life aboard the Jahan, will read much like a royal. Here is just teaser (note: this is not a spoiler warning – for that, you need to experience the Jahan in flesh) -  …see more

9 Photos

Houseboat | 2 Bedrooms | sleeps 50

Good 3.5/5 

1 night min stay

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from £80 /night

£560 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
2 bedroom Houseboat , premium standard and deluxe. at Alapuzha and kumarakom in Kerala  …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:

  • Great 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 3

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £73 /night

£510 - £772 / week

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Key info:

  • Great 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:

  • Great 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

8 Photos

Narrowboat | 1 Bedroom | sleeps 3

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £73 /night

£510 - £772 / week

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Key info:

  • Great 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 - £1256 / week

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Key info:

  • Great 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

12 Photos

Narrowboat | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £95 /night

£659 - £910 / week

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Key info:

  • Great 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

7 Photos

Narrowboat | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £92 /night

£639 - £975 / week

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Key info:

  • Great 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

10 Photos

Narrowboat | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £164 /night

£1142 - £1547 / week

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Key info:

  • Great 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 - £1547 / week

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Key info:

  • Great for children of all ages
  • 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