Family-friendly vacation rentals in Middlesbrough

Cheerful & Quaint 18th Century cottage

Pretty cottage situated on the village green in the heart of Castleton village. Open fire for creating a cosy night in & perfect for exploring the beautiful North Yorkshire Moors. Castleton is lucky to have two great pubs The Downe Arms with fabulous food and atmosphere right across the road and The Eskdale which serves lovely ‘fine dining food’ but also lovely just for a drink. There’s the Old Chapel Tearoom, Premier & ‘Off the Scale’ shop We are also along the Esk Valley train line to Whitby

Mabel Cottage - Stay in the heart of Stokesley

This charming cottage in the heart of Stokesley is the perfect retreat, with pubs, cafes, shops, and supermarkets all within walking distance. Enjoy an equipped kitchen, shower room, a Harrison (made in Yorkshire) king size bed, dining area and T.V . Ideally located, you’re just a short drive from North York Moors National Park, Roseberry Topping, Whitby’s historic seaside charm and more. Whether exploring or unwinding, this cottage offers everything you need for a memorable Yorkshire getaway.

‘The Penthouse’

This modern place to stay is perfect for anyone visiting the area;professionals,families&friends alike.Spread across the top floor of one of the largest houses in Marton,with it’s own guest entrance,it offers space,security&privacy. ‘The Penthouse’ comprises of2double bedrooms,a bathroom&open living area.There is also the option to turn a double room into a twin for flexibility. It has its own fridge,kettle,tea&coffee,workspace, TV&access to a utility(m’wave,toaster,airfryer,hob) for cooking.

Serendipity

Serendipity is one of three hand crafted wooden Shepherds Cabins, located on a working farm in the heart of Dalby Forest. (See Serenity and Dahlia Cabins on separate listings.) We're ideally situated just off the popular cycle routes and activity centres. The cozy en-suite cabin features a comfortable king size bed, fridge, heating, a gas BBQ on the covered veranda and continental breakfast. This luxurious cabin offers wonderful panoramic views in a tranquil setting. The perfect escape!

2 Bedroom House with Garden next to the River Tees

A modern 2 bedroom house with stylish furniture and decor. Large family living room with elegant kitchen/diner. En suite to master bedroom. This property is situated on the north shore development on the river tees. The property boasts a private garden from large french doors. A nearby footpath onto the river tees that takes you to tees barrage international white water center where you can take part in numerous water activities. It is also home to the Air trail climbing a cafe and pub/

Stoney Nook Cottage

Relax and unwind in this beautifully stylish space with wood burning fire. Located in central Guisborough, juts 2 minutes walk from the main town and shops, this stunning cottage has everything you need to relax. Beaches within a fifteen minute drive, stunning walks and North Yorkshires famous Roseberry Topping on the door step. The cottage boasts smart TVs throughout with super fast broadband and modern appliances. It hosts a master bedroom and bunk beds in the second bedroom

Cosy self-contained 1 bedroom studio flat

An entire cosy self-contained 1 bedroom studio flat with own kitchen and bathroom for complete privacy. The flat consists of 1xBedroom 1 x kitchen 1 x bathroom Centrally located in the historical market town centre of Bishop Auckland within walking distance of Auckland Castle, Mining Art Gallery, Auckland Tower, Kynren within an array of excellent pubs, restaurants, gifts and book shops on your door step. Ideal for contract workers or family visitors.

Swallow's Nest, Shepherd Hut, Family Farm Location

Swallow’s Nest, Shepherd Hut is an oasis of peace and quiet on its own tranquil garth setting, commanding beautiful views of the majestic Cleveland hills. We guarantee a stress free, relaxing stay on our wonderful family arable farm, surrounded by our lovely horses. Guests to Swallow's Nest will benefit from open countryside and lots of fresh air. Sit quietly overlooking the field wildlife pond to view a mixed variety of birds visiting the area.

Central | Spacious Penthouse | Stunning Views

Step into this luxurious 3-bedroom, 2-bathroom penthouse in the heart of Middlesbrough. With exposed brick, sleek modern design, a luxury bath, and stunning views over Albert Park, every room feels spacious and stylish. Sip drinks at your private bar, relax in the airy living spaces, and enjoy a short stroll to restaurants, shops, and the town’s vibrant attractions. The perfect blend of historic charm and contemporary comfort awaits.

Glamping Pod w/ BBQ Area & Onsite Café

🌿 Escape to Luxury on the Edge of the Durham Dales Wake up to fresh countryside air and your own beautifully crafted glamping pod. Set on the doorstep of the Durham Dales, enjoy peaceful views, modern comfort, and our on-site café serving breakfast, lunch, and homebaked cakes. Perfect for romantic escapes, family adventures, trips with friends or team retreats — it’s the ideal place to switch off and reconnect.

Upsall Grange Farm cottage

A beautifully renovated farmhouse with fantastic views of Roseberry Topping and the Cleveland Hills Snuggle up for a cosy evening in front of the wood burner The immaculate south-facing garden is a great place to relax on the furniture and fire up a BBQ. This cottage is 10 minutes away from Yorkshire moors and from many beautiful beaches. Please note, this property is on a Equestrian yard.

Romantic Yacht Stay on Hartlepool Marina

Stay aboard Tumbleweed, a cozy private yacht on Hartlepool Marina. Perfect for couples, solo travellers and adventurous small families, this unique waterfront stay includes fast Starlink Wi-Fi, smart TV with Prime Video and Netflix, Alexa, a compact kitchenette, and thoughtful extras including tea, coffee, milk, water and biscuits. A memorable coastal escape with real character.