Enjoy a delightful stay at Castell d'Emporda on our Catalan Classic Walk. Perched between the Pyrenees and the Costa Brava's cliffs, This superbly restored 700-year old castle is nestled between ancient olive trees and also holds Europe's largest scale model of the Battle of Waterloo.

Admire the architecture on our Self-Guided Walking in Puglia and Matera, where you’ll stay at Hotel Sassi overlooking the ancient honeycomb structures in Matera's Sassi district.

We’ve been carefully researching and sourcing the finest, friendliest and most charming hotels and characterful accommodations since 1985. Looking out for small, family-owned accommodations that take a genuine interest in their guests, we also keep an eye out for places whose menus epitomise the local cuisine.

Our accommodations offer much more than just a bed for the night. Many are historic properties, castles and palaces that have previously hosted monarchs, renowned artists and famous authors. All are individually selected, and because we have strong, trusted relationships with our hoteliers, you can expect a warm welcome wherever you go.

It's all in the Detail

Some of the places we feature are way off-the-beaten-track in mountain villages while others are in the heart of the most ornate historic centres. Many reflect the tastes and, at times, quirky styles of their owners, with all sharing a desire to provide "service plus" at every point of your stay.

If you’re looking to stay in a small family-run hotel, our Taste of Tuscany Walking trip allows you to stay at Agriturismo La Pietriccia, run by brothers Stefano and Simone near Chianciano, Italy. For a restored castle stay, our Contrasts of Catalonia Cycling takes you to the enchanting Castell d’Emporda which houses Europe’s biggest scale model of the Battle of Waterloo. If you’d like to stay in a modern hotel, complete with a wellness centre, our Cycling from Bruges to Brussels trip, takes you to Hotel Hotel Vé, a former fish smokehouse and cigar factory in 1923, located 450 yards away from Grote Markt.

Hotel ratings

Simply expand the day’s itinerary of the individual holiday pages to find out more about your accommodation. If the holiday is a single centre the hotel information will be shown only in Day 1. We clearly mark each accommodation with our own star rating for guidance purposes.

All our accommodation has been inspected and classified by the authorities of the relevant countries. As there is no direct British equivalent of many classifications, the broad expression ‘hotels’ refers to all the different types of accommodation we use, from friendly family-run B&B and country inns to luxury hotels (where is the country’s official hotel rating).

Headwater’s accommodation star ratings are provided to give you guidance on the relative standard of the accommodation you will be staying in. In most occasions this will match the official star rating of the accommodation, however, if we feel it necessary Headwater will adapt a rating to what we believe is fair. This is based on a variety of checks which can include property visits, customer feedback, facilities and location, or if the accommodation does not hold an official rating of its own. These ratings are reviewed regularly to ensure their accuracy and relevance for guidance purposes.

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Our favourite places to stay

Showing 31 out of 0 trips

Listed below are the holidays that match your search criteria. Use the filter options to refine your results.

Italy : Puglia

Self Guided Walking in Puglia: From Lecce to Matera

£1169


4.8 (73 reviews)

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Self-guided walking

7 nights,
hotel-to-hotel

Activity level: 2

Activity level: 2

Bed and
breakfast

Italy : The Dolomites

Walking the Dolomites of Alta Badia

£1669


4.9 (34 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level: 5

Activity level: 5

Breakfasts plus
4 meals

Italy : Sicily

Cycling through Baroque Sicily

£1729


4.5 (24 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
3 meals

Switzerland : Valais

Walking in Val d'Anniviers

£1889


4.7 (3 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level:<br>3,4 and 6

Activity level:
3,4 and 6

Half board

Germany : Bavaria

Walking in Southern Bavaria

£719


4.7 (64 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level: 3

Activity level: 3

Breakfasts plus
1 meal

Italy : Puglia

Contrasts of Puglia Cycling

£1409


4.6 (129 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
2 meals

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2319


4.8 (92 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
4 meals

United Kingdom : The Channel Islands

Walking in Jersey Premium

£749

NEW FOR 2027

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Self-guided walking

3 nights,
single centre

Activity level: 3

Activity level: 3

Bed and
breakfast

France : Champagne

Cycling the Vineyards of Champagne

£969

 
 

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Self-guided cycling

3 nights,
single centre

Activity level: 4

Activity level: 4

Bed and
breakfast

Italy : Italian Lakes

Cycling Lake Garda by e-bike

£1029


4.7 (6 reviews)

VIEW TRIP

Self-guided cycling

6 nights,
single centre

Activity level: 4

Activity level: 4

Bed and
breakfast

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£1039


4.7 (55 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
1 meal

Spain : The Canary Islands

Walking in El Hierro

£1059

NEW FOR 2027

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level: 4

Activity level: 4

Bed and
breakfast

Italy : The Dolomites

Cross-country skiing in the Dolomites

£1089


4.8 (4 reviews)

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Winter snow holiday

7 nights,
single centre

Half board

Printed route
directions

Spain : The Canary Islands

Walk the Bonita Island of La Palma

£1089

NEW FOR 2027

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Self-guided walking

7 nights,
single centre

Activity level: 5

Activity level: 5

Bed and
breakfast

Albania

E-bike Across Southern Albania

£1259


4.9 (22 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Activity level: 5

Activity level: 5

Bed and
breakfast

Spain : The Canary Islands

Walking on Gran Canaria

£1259

 
 

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level: 4

Activity level: 4

Half board

Austria : The Tyrol

Alpine Walks in the Stubai Valley

£1269


4.7 (16 reviews)

VIEW TRIP

Self-guided walking

7 nights,
single centre

Activity level:<br>3,4 and 6

Activity level:
3,4 and 6

Half board

France : Normandy

Normandy Walk from Deauville to Bayeux

£1369


4.5 (4 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Activity level: 1

Activity level: 1

Bed and
breakfast

France : Champagne

Cycle The Wine Route of Champagne

£1399


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
twin centre

Activity level: 4

Activity level: 4

Bed and
breakfast

Spain : Galicia

Cycle from Tui to Santiago in Style: Stay in Historic Paradors Hotels

£1439


5.0 (2 reviews)

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Self-guided cycling

6 nights,
hotel-to-hotel

Activity level: 5

Activity level: 5

Bed and
breakfast

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded Short

£1459


4.8 (4 reviews)

VIEW TRIP

Self-guided cycling

5 nights,
hotel-to-hotel

Activity level: 2

Activity level: 2

Bed and
breakfast

Spain : Extremadura

Cycling Central Spain in Style

£1519


4.7 (7 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Activity level: 5

Activity level: 5

Bed and
breakfast

France : Champagne

Cycling Champagne in Luxury

£1599

 
 

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Activity level: 4

Activity level: 4

Bed and
breakfast

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1639


4.8 (22 reviews)

VIEW TRIP

Self-guided cycling

11 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
2 meals

United Kingdom : The Channel Islands

Walking in Jersey, Guernsey and Sark Premium

£1769


5.0 (3 reviews)

VIEW TRIP

Self-guided walking

6 nights,
twin centre

Activity level: 3

Activity level: 3

Bed and
breakfast

France : The Loire

Cycling the Loire in Luxury

£1849


5.0 (1 reviews)

VIEW TRIP

Self-guided cycling

4 nights,
single centre

Activity level: 2

Activity level: 2

Breakfasts plus
2 meals

France : The Loire

Cycling The Chateaux Of The Loire - Upgraded

£1919


4.8 (8 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Activity level: 2

Activity level: 2

Bed and
breakfast

Italy : Puglia

Highlights of Puglia Cycling

£1939


4.7 (14 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
2 meals

United Kingdom : The Channel Islands

Cycling in Jersey, Guernsey and Sark Premium

£2069

 
 

VIEW TRIP

Self-guided cycling

6 nights,
twin centre

Activity level: 2

Activity level: 2

Bed and
breakfast

Italy : Piedmont

Gastronomic Barolo Walk

£2089


4.9 (102 reviews)

VIEW TRIP

Self-guided walking

8 nights,
hotel-to-hotel

Activity level: 4

Activity level: 4

Breakfasts plus
4 meals

Spain : The Canary Islands

Contrasts of Tenerife Walk (with transfers)

£2229

 
 

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Activity level: 5

Activity level: 5

Breakfasts plus
3 meals

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What our customers say

"Excellent relaxing holiday - accommodation was faultless."
Mrs Pitchforth, St Albans

"Fantastic accommodation and wonderful food!"
Mr Dickinson, Truro

"The locations were beautiful and the accommodation characterful and uniformly excellent, as was the food (and drink!) throughout."
Mr Larner, Dublin

"The accommodations and food were amazing and we would not have been able to find them on our own."
Mrs Merricks, USA

"The holiday was about as good as it gets, especially the accommodation and food, which was often provided in nearby restaurants."
Mr McGeoch, Bristol

"All accommodation was very good, with the Hotel Montmirail and Chateau de Mazan being truly excellent."Dr O'Grady, Warrington

"Our accommodation was superb at all three hotels and staff were friendly and knowledgeable."Mrs Reir, Inverurie

"The accommodation was delightful and made the most of the historical features."Dr File, Dundee

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