Family-friendly vacation rentals in Middlesbrough

4.91 out of 5 average rating, 335 reviews

A cozy sitting room is presented with a large mirror reflecting warm light from a chandelier. A television is positioned across from a log burner, surrounded by two armchairs and a comfortable sofa. Soft gray tones and decorative cushions contribute to the welcoming ambiance.

Cottage in Stokesley

Apple Tree Cottage. Stokesley.North Yorkshire.

A delightful old cottage overlooking West Green with a mix of antique, upcycled and vintage inspired decoration. The cottage is dog friendly, with a patio and large enclosed, secure garden. Located on the outskirts of the historic market town. The town has a distinguished wide cobbled high street lined with Georgian and Victorian buildings. It is served by banks,shops, up market restaurants and pubs. Surrounded by the Yorkshire Moors it makes an ideal base for exploring the Dales & East coast.

4.98 out of 5 average rating, 668 reviews

A well-lit bedroom features a spacious bed with patterned bedding, complemented by bedside lamps. A small wooden table with two chairs sits adjacent, creating a cozy dining area. Natural light streams through a skylight above, enhancing the inviting atmosphere of the room.

Condo in Stokesley

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.

Home in Marton-in-Cleveland

An open living area features a comfortable sectional sofa in a calming blue tone, paired with a natural wood table. Natural light enters through two skylights, illuminating the space with light neutral walls and a striped carpet providing a subtle contrast.

‘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.

4.95 out of 5 average rating, 148 reviews

4.95 out of 5 average rating, 155 reviews

A spacious studio features two single beds with coordinating bedding, positioned beside a media unit displaying various DVDs. A large television is mounted on the wall, and contemporary light fixtures hang from the sloped ceiling. A comfortable sofa is visible, creating a welcoming relaxation area.

Apartment in Trimdon

Cosy base for exploring from or break up a journey

Well equipped studio. Plenty of space for 3 to relax after a day of sightseeing or to take a rest mid journey. Unwind in the spacious walk in shower. Enjoy a relaxing drink in the garden or the large patio ( with or without the goats!). Perhaps even a BBQ ( gas BBQ available on request). Pop over the village green to the pub. Cosy down and prepare for your next adventure watching satellite T.V. Cook a light meal or order a take away. Very peaceful location and very comfortable accommodation.

Guest suite in North Yorkshire

A charming building features wooden siding and large windows that illuminate the interior. Surrounding the structure is a well-kept garden with diverse greenery and pathways, enhancing the outdoor ambiance. The picturesque setting is complemented by a stone patio area for sitting and relaxing.

*The Vicarage Annexe, Carlton, North Yorks 1BR S/C

The Vicarage Annexe is a beautiful, one double-bedroom facility situated at the foot of the Cleveland Hills. The building was originally built as a prayer and study room for the Vicarage. This is now a self-contained living area with en-suite facilities. The Annexe is located in the picturesque village of Carlton-in-Cleveland, which is in the North Yorkshire Moors National Park and this is an ideal location for a couple who enjoy the countryside for relaxing, sightseeing, walking or cycling.

4.98 out of 5 average rating, 400 reviews

4.9 out of 5 average rating, 425 reviews

The exterior of the modern house is showcased, with a brick façade and distinctive architectural features. A paved driveway leads to the front doors, which are flanked by minimal landscaping. Clear blue skies provide a bright backdrop.

Home in Stockton-on-Tees

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/

Condo in Saltburn Marske and New Marske

A wooden pier stretches toward a vibrant sunset, with pastel colors painted across the sky. The backdrop features historical seaside buildings, conveying a sense of charm. Gentle waves may be seen lapping at the shore along the sides of the pier, creating a serene coastal scene.

Kellys Place Saltburn by the sea (Sleeps 4)

Kellys Place This beautifully refurbished two bedroom apartment in the magnificent Zetland building located in the fantastic Victorian seaside town of Saltburn by the sea. Breath taking sea views from all of the rooms. The double bedroom boasts a wake up view of the of the sea and if you are an early bird it also benefits from the most amazing sunrises which you can see rise over the horizon. Allocated with a numbered free parking space provided prior to your stay so hassle free.

4.88 out of 5 average rating, 304 reviews

4.98 out of 5 average rating, 128 reviews

Cottage in Stokesley

Townhouse in Stokesley

A delightfully old, mid-terraced townhouse situated in the conservation area of West Green, Stokesley. The house has been sympathetically decorated and furnished to reflect its heritage, with a beautiful collection of traditional, upcycled and vintage inspired furniture to support independent, local businesses. We are dog friendly. Outside we have a secure, seated courtyard. Stokesley and the local area hosts all manner of restaurants and cafes, many of which are dog-friendly.

Guest suite in Great Ayton

A small patio area is depicted through open double doors, showcasing a circular table surrounded by four chairs. Lush greenery and a well-maintained garden provide a serene backdrop, with potted plants adding to the inviting outdoor setting.

Riverside Guest Annexe

Riverside guest annexe is in a secluded garden but is within 50m of Waterfall Park and Great Ayton High Green, with its shops, pubs, cafes, take-aways and Tourist Information. The annexe is attached to our house, but has its own entrance, patio, garden area and parking space. We can accommodate 2 adults comfortably, plus a third adult or up to 2 children on our pull-out and/or sofa bed. We provide bedding, towels and toiletries. No smoking or pets are permitted in the annexe.

4.96 out of 5 average rating, 211 reviews

4.97 out of 5 average rating, 137 reviews

A modern living area is presented with a plush purple sofa and a sleek glass table. Lush green ferns and a white orchid arrangement enhance the space. Mirrored panels reflect light, and a unique antler chandelier offers a warm illumination above.

Condo in Middlesbrough

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.

4.9 out of 5 average rating, 137 reviews

A spacious outdoor seating area is presented, featuring a comfortable sectional sofa and a coffee table on a brick patio. Surrounding gravel adds texture, while the well-maintained lawn and traditional brick walls frame the inviting space. The exterior of the farmhouse is visible in the background.

Home in Guisborough

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.

4.94 out of 5 average rating, 286 reviews

A comfortable armchair with a patterned cushion is positioned beside the stone fireplace. The multi-fuel stove is set within a white mantel, surrounded by natural textures and tones. A small lamp and decorative items add warmth to the inviting sitting area.

Cottage in Guisborough

Cosy 1-bedroom cottage with indoor log burner

Staying at Wrens Nest Cottage is an experience in itself. With a compact and cosy feel it instantly makes you feel at home and relaxed. Located just a stones throw away from the market town centre and a perfect distance from so many attractions, you will want to come back time and time again. See our Instagram page @wn.cottage #wrensnestcottage

Popular amenities for Middlesbrough family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in North Yorkshire

The private patio area is surrounded by lush greenery, featuring comfortable outdoor seating and a table. A modern structure is visible in the background with large windows, allowing natural light to fill the interior. The space is designed for relaxation and enjoyment.

Luxury 1 bedroom lodge with hot tub and fire pit

4.91 out of 5 average rating, 333 reviews

Tiny home in North Yorkshire

Magical A-Frame Wooden Cabin Nestled in Woodland

4.96 out of 5 average rating, 121 reviews

Cottage in Skelton-in-Cleveland

The exterior of Sundial Cottage is presented at dusk, showcasing a charming two-story structure with a welcoming front porch and multiple windows. A spacious brick pathway leads to the entrance, while the surrounding areas feature subtle landscaping and outdoor lighting, enhancing the cozy appearance.

Sundial Cottage, Stunning 3Bed Cottage with Hottub

4.94 out of 5 average rating, 179 reviews

4.98 out of 5 average rating, 380 reviews

The Yurt is surrounded by lush greenery and yellow gorse flowers, positioned within a natural depression of the landscape. A clear blue sky with scattered clouds stretches overhead, while the distant hills create a scenic backdrop.

Yurt in Glaisdale

Curlew View

4.92 out of 5 average rating, 136 reviews

The exterior of a modern cabin features dark wood paneling and large windows. A set of steps leads up to the entrance, and the surrounding area has been landscaped with gravel and wooden edging, showcasing a neat and tidy presentation.

Cabin in Great Broughton

Moor View Luxury Log cabins

4.99 out of 5 average rating, 159 reviews

A spacious outdoor deck is surrounded by greenery, featuring two Adirondack chairs and a round fire pit with a gentle flame. Potted plants add a touch of nature, while soft lighting illuminates the area, creating a cozy atmosphere for evening relaxation.

Treehouse in Richmond

The Pines Treehouse @ Treetops Hideouts

4.98 out of 5 average rating, 185 reviews

The bungalow is set in a vast green landscape, surrounded by mature trees and shrubs. A large lawn area extends towards the tranquil Hurworth Burn Reservoir, with the property offering a peaceful retreat in a rural setting.

Bungalow in Wingate

Celebration House with hot tub and reservoir views

4.98 out of 5 average rating, 296 reviews

Cabin in Ugthorpe

The Highlander

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 382 reviews

A spacious bedroom features a large bed with neatly arranged linens and towels. Two bedside tables flank the bed, each fitted with wall-mounted lamps. A mirror stands beside a shelf displaying books. Natural light streams in from a nearby window.

Cottage in Great Ayton

Spacious barn conversion in North Yorkshire

4.83 out of 5 average rating, 224 reviews

A framed artwork of the Yarm Viaduct is displayed on the wall. The illustration features the iconic bridge, with stylized depictions of surrounding houses in a vibrant colour palette, capturing the essence of North Yorkshire.

Guest suite in Yarm

Layfield Lodge

4.87 out of 5 average rating, 173 reviews

A modern dining area features a stylish white table surrounded by six chairs, with a decorative bowl placed at the center. Natural light enters through a large window, illuminated by a contemporary light fixture. A glimpse of a kitchen area and a small workspace is visible.

Townhouse in Guisborough

The Beehive, modern two-bed, close to town centre

Camper/RV in Redcar and Cleveland

'Beachside' - next to the beach with sea views

4.95 out of 5 average rating, 122 reviews

Cottage in Stockton-on-Tees

A warm living area features wooden beams and a brick fireplace. A cozy sofa with cushions pairs with an armchair, while a dining table is positioned nearby. Soft textures from the rug complement the wooden flooring, creating a welcoming environment.

Cosy cottage off Yarm Highstreet

4.95 out of 5 average rating, 260 reviews

4.93 out of 5 average rating, 100 reviews

A spacious living area features a comfortable beige sofa facing a large wall-mounted television. Exposed wooden beams add character to the ceiling. A soft glow is provided by a round ceiling light, while a small window allows natural light to brighten the room.

Cottage in Yarm

Bridge Cottage

Cabin in Redcar and Cleveland

10 Metres From Beach Front Free Wifi No Guest Fees

4.92 out of 5 average rating, 126 reviews

4.93 out of 5 average rating, 99 reviews

A cozy living area features a light-colored sofa paired with a matching armchair, alongside a wooden coffee table. A fireplace with a wooden mantel serves as a focal point, while framed artwork adorns the walls. Light enters through a nearby window, creating a warm ambience.

Home in Stockton-on-Tees

Charming cottage

Family-friendly home rentals with a pool

4.81 out of 5 average rating, 129 reviews

A comfortable seating area is showcased, featuring a patterned couch adorned with two decorative pillows. A piece of artwork is displayed on the wall above, while natural light enters through large windows fitted with light curtains.

Cabin in County Durham

Well located lodge

4.97 out of 5 average rating, 121 reviews

The exterior of a modern cabin is surrounded by a gravel terrace, featuring two black chairs and a table. A hot tub is positioned nearby. Large glass sliding doors invite natural light into the interior while showcasing views of the surrounding landscape.

Cabin in Ferryhill

Luxury Cabin with Hot Tub & Spa Facilities

5.0 out of 5 average rating, 14 reviews

A scenic view of Beech Farm showcases a gravel courtyard surrounded by stone cottages with traditional roofs. Greenery and flowering plants enhance the space, while outdoor seating areas invite relaxation. The peaceful environment is complemented by sunny skies and a well-maintained landscape.

Cottage in Wrelton

Pool, playroom, animals & more in a 2-bed cottage

Camper/RV in County Durham

A comfortable living area is presented with a large sectional sofa adorned with various decorative cushions. A round coffee table sits at the center, while a television is placed on a wooden cabinet. Sheer curtains frame the windows, allowing natural light to fill the space.

Holiday park in Crimdon Dene

4.85 out of 5 average rating, 34 reviews

Apartment in County Durham

A bright balcony view features a serene sunrise reflecting on calm sea waters. The image highlights sliding glass doors that open onto the balcony, framed by soft white curtains. The horizon showcases gentle waves, creating a peaceful coastal atmosphere.

Sea view holiday home

4.92 out of 5 average rating, 89 reviews

Tiny home in County Durham

Woodlands Dene-Crimdon Dene HolidayPark-Accessible

5.0 out of 5 average rating, 3 reviews

Guesthouse in County Durham

Caravan in Yorkshire

4.78 out of 5 average rating, 64 reviews