Cleveland Way - 11 Days & 10 Nights

The Feathers is a local landmark standing on the bustling market square in Helmsley. The Feathers offers a blend of historic charm and traditional Yorkshire hospitality. You can enjoy informal dining in the Feversham bar or a quiet drink by the fire in the Pickwick bar.  Wherever possible they aim to use locally sourced, fresh ingredients.

The site of The Black Swan dates back to the 15th century, the house itself comprising of a Tudor house, a Georgian house, and an Elizabethan house.

This accommodation offers a warm welcome with cosy rooms, an in-house bar and restaurant, and easy access to Rievaulx Abbey, Helmsley Castle and Helmsley Walled Garden.

This charming stone cottage is situated in the middle of picturesque Helmsley, close to the North York moors and nestling by the Hambleton and Howardian Hills. 

The Forresters Arms Bed and Breakfast is situated in the picturesque village of Kilburn, 1 mile from Sutton Bank. All rooms are en-suite with a bath or shower, rooms have tea / coffee facilities, hairdryer, TV and alarm clocks. The restaurant allows you to dine in style with professionally waited-on service whilst enjoying a relaxing light and rustic feel. Choose from the comprehensive menu and enjoy delicious, traditional food that they have become famous for. All the food is made from fresh ingredients and sourced locally where possible.

An 18th Century stone inn overlooking the market cross of Osmotherley. The bedrooms are fresh and modern with oak doors and skirting as well as handmade oak wardrobes.

The Queen Catherine Hotel is a family-owned pub offering food and accommodation in the heart of the North Yorkshire Moors. The hotel has a small selection of comfortable and well-appointed bedrooms, all of which have just been highly refurbished.

Family owned, with an increasing reputation for high quality, freshly prepared food. The atmosphere at the Three Tuns is always warm, friendly and relaxed and the Rennie Mackintosh inspired interior décor is a delight. The residents lounge is designed to make you feel as though it’s your own home. 

Combining the service and facilities of a Silver Award Winning three-star hotel with the atmosphere of a Yorkshire country inn. The Wainstones provide a friendly and comfortable stay for walkers.

The Buck Inn is located in South Chop Gate. The owners extend a warm, friendly welcome at the Buck Inn. Set amidst the rugged splendour of Bilsdale, the Buck Inn offers all the traditions of an English country tavern. The inn provides comfortable accommodation, all guest rooms are situated on the ground floor with private access to the large car park to the rear of the building.

A quintessential country pub with rooms in picture-postcard Newton under Roseberry, The King’s Head Inn is your gateway to Captain Cook Country. Beneath iconic Roseberry Topping, the inn has a is surrounded by peaceful countryside and forests

This family-owned hotel has an enviable reputation spanning over 20 years and is highly-regarded in the region for providing an extensive menu of locally-sourced food.

The family-run Spa Hotel is an imposing sight, boasting unrivalled panoramic views of Huntcliff, the North Sea and beautiful surrounding countryside.

Ensure you book a table at their recently refurbished restaurant. We recommend timing it with the sunset! 

Welcome to the Victorian guesthouse in the heart of Saltburn and only a five-minute walk from the beach. Features of the rooms include polished floorboards, original water colours, Victorian brass beds, and an open fireplace.

Found directly on the Cleveland Way (the trail runs through its car park!), the Runswick Bay Hotel is a delightful five-bedroom en-suite hotel located at the top of Runswick Bay; a picture postcard North Yorkshire coastal village, boasting a mile of the secluded bay and gorgeous beach. 

The Firs Guesthouse offers true Yorkshire Hospitality at its best, a large detached Victorian property with many of its original features, such as doors, floors, skirting boards, and picture rails. It offers 12 cosy rooms and has a wonderful in house seafood restaurant.

The Villa was built in 1892 as a lodging house, the first of its kind, at the top of Bay Bank. This Victorian property has been lovingly restored retaining all its original features; servant bells, original cast iron fireplaces in all bedrooms and a cast iron range in the kitchen. 

A large detached Victorian House in Robin Hood's Bay, built-in 1897 by Captain Jacob Storm. Lovingly restored with many original features and located a short stroll away from the beautiful cobbled streets which wind down to the sea, passing a variety of local restaurants, pubs and shops.

The Victoria Hotel is a landmark hotel on the cliff top at Robin Hood's Bay. The building is a superb example of a Victorian Hotel built around 1897 with a fantastic open, wooden staircase. The hotel boasts spacious rooms, free wifi, sea view restaurant, and sea view tea room. 

The property has been beautifully restored and retains many original features. All 7 rooms are individually designed, decorated to a high standard and benefit from ensuites. With all the modern comforts you would expect to make your stay special such as top of range beds, luxury Egyptian cotton linen, thick fluffy towels, free high-speed WiFi, flatscreen UHD Smart TVs (with Netflix and other on-demand services) and stocked with Noble Isle toiletries. 

There is no such thing as a standard room at The Waves. Each of their 7 rooms are unique – individually decorated and furnished to reflect the elegance of the late victorian building, with the added benefit of state-of-the-art Smart TVs and luxury beds.

A bright, modern hotel in the heart of Scarborough with all the facilities walkers could wish for including a boot washing station and drying area! Add to that comfortable and spacious rooms and a warm welcome and you'll be sure of a lovely stay in Scarborough! 

All Seasons Guest House is a family-run bed and breakfast which has recently been refurbished to a high standard. This boutique guest house combines contemporary elegance and modern convenience with traditional warmth and hospitality. All Seasons is a 5 Star Gold awarded guest house.

Rutland West is a restored Edwardian family run B&B ideally located between the beach and the town center.