Family-friendly vacation rentals in Pickering

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Top-rated family-friendly rentals in Pickering

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in West Ayton

4.94 out of 5 average rating, 123 reviews

Cottage near Scarborough fab country views parking

East Wing cottage in a picturesque quiet conservation area by the Old Mill in North York Moors National Park. Acre of gardens overlooking 13th century Ayton Castle and River Derwent. Artificial grass tennis court. 4 miles from beach & sea. Quality furnishings. Spacious cosy for couples/families. Back gate access to countryside wood river walks Sky BT sports Netflix Amazon 5 min stroll to village pubs, excellent fish restaurant, take-away, supermarket, petrol station. 4 golf courses close by.

Apr 7 – 14

R3,097 ZAR per night

Guest favorite

Cottage in East Riding of Yorkshire

4.97 out of 5 average rating, 328 reviews

The Hayloft at Bainton - 2 bedroom cottage.

The Hayloft provides self catering holiday cottage accommodation fitted out to a high standard. The property is located in the pretty little village of Bainton situated in the heart of the Yorkshire Wolds close to many tourist destinations such as Beverley, Hull, York and the east coast. The cottage has a private gravelled garden area with outdoor furniture, set within one acre of private land and includes off road parking. We welcome two well behaved dogs but they must not be left unattended.

Jul 19 – 26

R2,752 ZAR per night

Guest favorite

Cottage in Robin Hood's Bay

4.87 out of 5 average rating, 106 reviews

Burton House - on the seawall in Robin Hood's Bay

Burton House is a cosy 18th Century holiday cottage located 5 meters from the seawall at the top of King street and Chapel Street in the heart of the picturesque coastal village of Robin Hood's Bay . The house is packed full of traditional Victorian features and home comforts. The back of the house faces the sea and provides direct sea views from a number of small windows including the infamous "loo with a view". The beach, pubs, shops and cafes are a 2 minute walk along family friendly paths.

Dec 6 – 13

R2,447 ZAR per night

Guest favorite

Apartment in North Yorkshire

4.94 out of 5 average rating, 378 reviews

Studio 43 Filey

Studio 43 is a modern studio set in the picturesque coastal town of Filey and is also within easy reach of york and many other coastal and country villages and towns. This studio is finished to a very high standard, accommodating up to 4 adults with one off road parking space and plenty of free street parking. The Kitchen/Living area couples with the bedroom where there is a comfortable double bed (sofa bed in the living area). There is a bathroom with basin, towel rail, toilet and shower.

Jan 23 – 30

R1,515 ZAR per night

Guest favorite

Loft in Masham

4.91 out of 5 average rating, 315 reviews

The Old Masham Library - Grade 2 listed

The Grade 2 listed Old Library, Masham sits on the corner of the principle approach in to the Market Square from Swinton. Built in 1856 it originally served as the Mechanic Institute of then Mashamshire. It was designed by the respected William Perkin of Perkin and Backhouse of Leeds in Victorian Italianate style. In 2017-18 its internal was redesigned and fully refurbished by Langton Holdings Ltd. On the side of the building is 7kw EV charging by podpoint so be sure to download the app!

Oct 3 – 10

R2,981 ZAR per night

Guest favorite

Home in Pickering

4.86 out of 5 average rating, 182 reviews

Lark Cottage Pickering 18th Century

Beautiful 18 Century cottage recently renovated with vintage vibe and antique furniture low beams with an open gas fire for that cosy romantic get away. Steps from Pickering Castle, shops, cafes, Restaurants and Lark Cottage is set in the center of Pickering, a historic market town, which serves as the gateway to the North Yorkshire Moors National Park and Heritage Coastline. This attractive stone built Grade 11 listed cottage is ideally situated for exploring the beautiful countryside.

Oct 23 – 30

R2,215 ZAR per night

Guest favorite

Home in East Riding of Yorkshire

4.94 out of 5 average rating, 406 reviews

Beautiful and stylish barn conversion near York

The cottage is a Grade II listed barn conversion offering a welcoming base for your stay. Heating is provided by a biomass boiler, so very eco friendly. There is also a wood burning stove to keep you cosy. We are in a quiet village called East Cottingwith: a fantastic base for visiting York and touring Yorkshire. Ideal for cyclists, bird watchers, walkers and anyone who wishes to enjoy a rural location close to the attractions of the city of York. There is no regular public transport.

Nov 26 – Dec 3

R2,341 ZAR per night

Guest favorite

Farm stay in Langdale End

4.97 out of 5 average rating, 269 reviews

Dahlia Cabin

Our third luxury handcrafted log cabin, set on a working farm in the heart of Dalby Forest. Perfect for couples or families. Our cozy, heated cabin has a fridge and kettle with tea and coffee making facilities, and has an ensuite bathroom with heated towel rails. Enjoy the stunning views from the covered raised decking area. Close to Dalby visitors center and 30 miles of amazing mountain bike trails. We provide a continental breakfast brought to the door, and a gas bbq for cooking.

Oct 6 – 13

R2,066 ZAR per night

Guest favorite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Braecote is a peaceful, warm, and welcoming cottage in the picture perfect village of Coxwold. With wide grass verges, honey coloured stone houses and a traditional country pub just up the road, Coxwold is one of the prettiest villages in North Yorkshire. York, Harrogate, Helmsley and Malton are close by, the North York Moors, Yorkshire Dales and east coast all within easy reach. Newburgh Priory is just up the road and Michelin starred Black Swan at Oldstead a short drive away.

Dec 9 – 16

R2,434 ZAR per night

Guest favorite

Apartment in North Yorkshire

4.99 out of 5 average rating, 170 reviews

Private Garden Apartment With Off Road Parking.

Spacious, relaxing, south facing, Georgian apartment with private garden. Located in the heart of Scarborough's historical Old Town. Ensuite bedroom with super king bed (2 singles upon request). Galley kitchen with full cooking facilities. Secure off road parking for one vehicle (enquire if very large). Wifi, TV, DVDs, books & games galore. 5 mins walk to beach, harbour, castle & local market. 15 min walk to town centre shopping & train station. Check in from 3pm-10pm.

Jul 17 – 24

R3,230 ZAR per night

Guest favorite

Cabin in Huggate

4.99 out of 5 average rating, 183 reviews

1 Bedroom Lodge (Hot Tub) - On top of the Wolds

Wolds Away offers luxury lodge accommodation in a tranquil environment with beautiful views across the fields and dales of the Yorkshire Wolds. The lodge comes with a private Hot Tub, private parking and is perfect for a couple wishing to enjoy a romantic getaway or for anyone just wanting time to unwind. Newly built, stunning position looking over the Yorkshire Wolds. Super-king bed, quality bed linen. Log effect fire, smart TV's. Luxury bath products , towels , gowns .

Jan 5 – 12

R3,453 ZAR per night

Guest favorite

Guest suite in Sutton-on-the-Forest

5.0 out of 5 average rating, 224 reviews

Countryside location near to York

Nestled in the countryside just outside York, 'The Kennel' is a relaxing and peaceful retreat. This small but perfectly formed self-contained annex is set in three acres of newly planted woodland in which you can often see the Barn, Tawny and Little Owls visiting to be fed from the feeding posts, garden, small orchard, wildlife pond and apiary housing up to 8 beehives which provide us with some delicious honey. To the rear of the property is a Whisky and Gin Distillery.

Feb 3 – 10

R1,961 ZAR per night