Cleveland and Hambleton
Helmsley Garden Cottage & Railway Carriage
This little oasis is as luxurious as any of Helmsley’s three Market Square hotels but, although still very central, is far quieter and more intimate. There are two choices of self-catering accommodation: two people (three at a push) in the cottage or four in an amazing converted Victorian railway carriage in the back garden. What makes this place extra special is the quality of service and attention to detail given by owners Louise and Richard Craig.
Laskill Country House
Near Hawnby, YO62 5NB
The tiny hamlet of Laskill in Bilsdale is almost entirely a family-run holiday village, with Mandy at the helm. The main house can sleep ten to 12 people in five bedrooms, with seven satellite cottages sleeping two, four or six. The standard package for all of the properties is now self-catering but it’s still possible to have B&B, or even full board, by going for the bespoke option of having a private chef for your stay – proper luxury! You can have a quiet, get-away-from-it-all stay with excellent walks from the door, the ancient Quaker meeting house over the road and fly-fishing on the nearby River Seph; alternatively, you could do what I did and take over all of the accommodation to sleep 40 for a family event – my wedding, as it happens. Prices are reasonable and dogs are welcome.
Hawsker, YO22 4JZ
Let’s clear up any confusion right from the start; this is not one of the prominent lighthouses on the piers in Whitby Harbour but a clifftop building a couple of miles southeast near the village of Hawsker; locals call this one ‘Whitby High Light’ to avoid confusion. The lighthouse is still operational and owned by Trinity House but was automated in 1992 – holiday accommodation is in the two former keepers’ cottages (Galateaand Vanguard). Both can sleep five people in three bedrooms but only Vanguardallows dogs. This is a place to stay if you love isolation and exposure as the lighthouse is perched right on the edge of a 200ft cliff and with no Wi-Fi and limited phone signal. A sketchy farm track provides the only access, and the Cleveland Way path passes close by on its way to Robin Hoods Bay.
Boggle Hole YHA
Robin Hood’s Bay, YO22 4UQ
This unusual building is not in Robin Hood’s Bay village but on Robin Hood’s Bay itself, Boggle Hole being an old smugglers access point to the beach. The building is a big ex-watermill tucked into the steep valley of Mill Beck just before it flows into the sea. It boasts 85 beds, a café, bar and meeting room but by far its best attributes are proximity to the beach, wild cliff coastline and its isolation. Boggle Hole is only accessible on foot, either from a car park a quarter of a mile up the hill or half a mile along the beach from Robin Hood’s Bay (when the tide is out!). As this is a youth hostel, the rooms are basic but they are very cheap and there are lots of smaller twin and family rooms including some en suites. Ask for a quiet one if there’s a school party in.
Fylingthorpe, YO22 4TH
What a great thing to be able to say… ‘the place I stayed in on holiday was an absolute pigsty!’ But that really is what this building was. Squire Barry of nearby Fyling Hall visited the Mediterranean in the 1880s and was very taken by the Classical architecture he saw there. On his return he decided to build his new pigsty in the same style, columns and all. The Landmark Trust has converted it into a self-catering cottage for two with one double room at its usual not-so-affordable price. No dogs.
Staintondale, YO13 OEL
Back in the early 18th century a Staintondale Quaker by the name of William Worfolk bequeathed money in his will towards the building of a meeting house locally, so one was constructed with this cottage adjoining. The meeting house is long gone but the cottage still belongs to the Society of Friends and they have renovated it with a respect for the environment informed by their religious beliefs. Worfolk Cottage is officially carbon-neutral due to a combination of ground source heat pump, wind turbine, solar panels and top-class insulation. It is now offered as self-catering accommodation for up to 14 people in five bedrooms and at a very reasonable rate.
Howardian Hills and Ryedale
Cherry Tree Lodge
Welburn, YO60 7DX
Cherry Tree Lodge is a two-bedroomed bungalow sleeping four people, with a lovely mixture of traditional and modern. The building is timber clad with a brilliant wood-framed, covered patio area but the indoor facilities are brand new and stylish. Although right in the middle of Welburn, privacy, peace and quiet are ensured by the lodge’s position behind the High Street frontage. The village pub is only yards away and, for fresh and tasty supplies, Dogh deli and bakery is even closer; they also do delicious breakfasts from 8am in their café so you won’t need to cater for yourself first thing in the morning if you’re feeling lazy.
Secret View Cottage
Terrington, YO60 6PB
Although the address is Terrington, Secret View Cottage is a mile out of the village, tucked behind Flat Top Farm on the Hovingham road. It is the middle one of a row of stone cottages and sleeps up to three people in two bedrooms. As its name suggests, the views from the top of Terrington Bank are stupendous, and nearby public footpaths allow some lovely local forest walks. The Yorkshire Lavender Farm and Café are within walking distance, and the beautiful village of Hovingham is just a three-mile drive away.
Country Huts on the Wolds
Thixendale, YO17 9TG
These two wooden shepherds’ huts are sited on a sheep farm and next to Thixendale village cricket pitch, hence their names – Wool and Wicket. Wool sleeps two in a king-size bed while Wicket also has a set of bunkbeds so sleeps four. Both have a bathroom, kitchen, wood-burning stove and outdoor fire pit. The Yorkshire Wolds Way and Centenary Waylong distance footpaths go virtually past the door. Because of the farm location dogs can’t be catered for.
North Duffield, Y08 5DE
Skipwith Station is handy for the Pocklington Canal and the city of York and certainly qualifies as a special place to stay. Or, rather, special places to stay as there is more than one choice on offer. In memory of the Derwent Valley Railway that ran through here until 1985, owners Mary and Graham Attwell offer three old railway carriages and a loading and storage bay that have been converted into self-catering accommodation sleeping from two to six, some of which are dog friendly.
Baille Hill House
Bishopthorpe Rd, YO23 1GH
With space for ten guests in five bedrooms, this is an ideal venue to base a city break for an extended family or large group of friends. Rental prices start at £995 per week so you can stay here for less than £100 per person per week if you fill the place. In York, getting around can be a nightmare so location is paramount and Baille House is central enough for everything of interest to be within walking distance. Two of the city’s best walking routes, the medieval walls and the riverside, are right on the doorstep and Rowntree Rark is five minutes away. Car parking is at a premium in the city centre but Baille House has three free spaces for guests. Not suitable for dogs.
The Little House
Bishopthorpe Rd, YO23 1JS
This ex-doctor’s surgery is known locally as the smallest house in York, hence the name. Not surprisingly it only sleeps two in one bedroom but has all of the facilities necessary for a very comfortable stay. Being so close to the city centre, car parking can be awkward; my advice would be not to bring a car at all as the train station is close by and everywhere else of interest is within walking distance. The most scenic pedestrian route into the city centre from here takes you through Rowntree Park and along the riverside.
For more information, see Mike Bagshaw’s guide: