Vacation rentals in Middlesbrough

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Top-rated vacation rentals in Middlesbrough

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Guest favourite
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.
Home in Marton-in-Cleveland
4.95 out of 5 average rating, 117 reviews

‘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 with Microwave,Toaster&hot plate for cooking

Top guest favourite
A charming cottage with a red-tiled roof is situated alongside a pebbled pathway. The inviting exterior features a mix of brick and stone finishes, with white-framed windows. Adjacent, a historic stone church with a tower is visible, creating a serene backdrop amidst a well-maintained garden.
Cottage in Carlton-in-Cleveland
4.97 out of 5 average rating, 164 reviews

Old Fire Station Cottage, EV point Opt. 2nd B’room

Contemporary Comfort in a Charming Cottage – Carlton-in-Cleveland, North York Moors National Park. Perfect for a quiet escape or an active adventure, this beautiful cottage offers everything you need Fast, reliable Wi-Fi & Smart TV Welcome goodies: fresh milk, coffee, sugar, tea, and delicious homemade cake Just a short stroll away, enjoy authentic Thai cuisine and top-notch real ales at the friendly village pub, The Blackwell Ox – also offering excellent takeaway options. EV Charger by App

Top guest favourite
A self-contained studio apartment features a spacious bed with light blue bedding. A dining table with black chairs is positioned near a window that offers views of the countryside. The well-equipped kitchen is visible, with modern appliances and counter space.
Apartment in Stokesley
5 out of 5 average rating, 329 reviews

The Studio, near Stokesley

Our self-contained studio apartment has a shower room, store room, well equipped kitchen, superking bed ( Available as 2x3ft. singles if required), a terrace & garden overlooking open countryside with uninterrupted views of the Cleveland Hills & Captain Cook's Monument. It is a 3 min drive/15min walk to the bustling town of Stokesley where there are restaurants, cafes, pubs, shops, supermarkets, take-aways, a weekly Friday market and a popular Farmers' Market on the 1st Saturday of the month.

Top guest favourite
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.
Guest suite in North Yorkshire
4.98 out of 5 average rating, 319 reviews

*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.

Top guest favourite
The exterior of Hillfoot Cottage is framed by lush greenery and trees, providing a sense of privacy. The white cottage features a welcoming front door and two windows, complemented by a well-maintained garden area with hedges and a wooden gate marking the entrance.
Cottage in Yearby
4.97 out of 5 average rating, 201 reviews

Hillfoot Cottage - charming country character.

Hillfoot Cottage is a cosy and comfortable 350 yr old cottage which began life as a pig sty in the quiet country village of Yearby, near Redcar. Offering peace and tranquility with local walks on your doorstep. Located a short drive to the seaside town of Redcar and Market town of Guisborough, within 1/2 hours drive to the North York Moors National Park and Whitby and within 1 hours drive to the Yorkshire Dales. An abundance of wild birds are to be found in the gardens of our cottage.

Top guest favourite
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
4.96 out of 5 average rating, 110 reviews

3 Bed Penthouse | Spacious | Central Location

A luxurious and modern airbnb located in the heart of Middlesbrough. This stunning penthouse is owned by a friendly family comprising of Idris, Maggie, and their sons Mark and Ross. Built in the late 1800s, this penthouse has been newly refurbished while keeping its original charm and character. The location is perfect for exploring the town and its surroundings, and only a short drive away from amazing countryside and beaches. Book now to enjoy the very best of Middlesbrough.

Superhost
The exterior of a modern two-bedroom house is showcased, featuring a spacious roof terrace and large windows framed by greenery. The brick facade is complemented by bicycles parked near the entrance, with garage doors visible to the right.
Home in Stockton-on-Tees
4.86 out of 5 average rating, 614 reviews

2 Bedroom Riverside Property with Roof Terrace

A very large modern 2 bedroom house with open concept living and kitchen. En suite from master bedroom. This property is situated on the north shore development on the river tees. The property boasts a roof terrace to enjoy and a private courtyard. 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.

Top guest favourite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny homes in Urra
4.98 out of 5 average rating, 142 reviews

Maltkiln House Annex North Yorkshire moors

Get away from it all, unplug and unwind. Maltkiln House Annex is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast.

Top guest favourite
A wooden deck features steps leading up to a blue shepherd hut with a solid wooden door. Two metal chairs and a small table are set on the deck, surrounded by gravel. A folding chair is positioned nearby, with a flower box hanging by the entrance.
Shepherd’s hut in Hilton
4.98 out of 5 average rating, 103 reviews

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.

Superhost
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
4.83 out of 5 average rating, 177 reviews

Self contained annexe with kitchenette & en-suite

This modern yet cosy self contained open plan annexe is perfect if you want to enjoy what Yarm has to offer. It’s a short 0.4 mile walk to the heart of the high street which is filled with boutique shops, restaurants, cafes & bars – it’s easy to see why it was named the winner of the 2020 Rising Star award at the Great British High Street Awards. Plenty of off-street secure parking also available at the property.

Superhost
A neatly arranged bedroom is presented, featuring a spacious bed with white linens and decorative pillows. Two side tables with stylish lamps provide soft lighting. A patterned accent wall brings visual interest, while a cozy navy throw lies at the foot of the bed.
Home in Thornaby
4.89 out of 5 average rating, 185 reviews

Perfectly located little house in Stockton-on-Tees

Perfect for a single person or a couple. Modern and cosy. Everything you could need for a trip to Teesside. Excellent location for multiple transport links and local attractions. Close to A66. 15 minute walk to Thornaby Train Station. 15 minute drive or taxi ride to Yarm for great nightlife, bars and places to eat. 20 minute drive to Teesside Airport. Stockton and Teesside Park 5-7 minute drive.

Guest favourite
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 Redcar and Cleveland
4.91 out of 5 average rating, 114 reviews

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.

Popular amenities for Middlesbrough vacation rentals

Quick stats about vacation rentals in Middlesbrough

  • Total rentals

    380 properties

  • Nightly prices starting at

    $28 CAD before taxes and fees

  • Total number of reviews

    4.8K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

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