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Vacation rentals in Middlesbrough

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Top-rated vacation rentals in Middlesbrough

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cottage in Staithes

4.81 out of 5 average rating, 160 reviews

17th Century fisherman's cottage + stunning view

Wake up to this stunning view, relax, and enjoy your morning coffee, afternoon tea or early evening G&T sitting outside our traditional cottage gazing at the fishing boats in the beck, higgledy-piggledy rooftops or out to sea. Regularly stayed in and painted by artists, this charming 17th Century cruck-beamed fisherman's cottage is quaint and cosy + open fire-ideal for a romantic getaway or walking holiday. Mortimer & Whitehouse stayed and filmed their Gone Fishing Christmas Special here 2020.

Guest favourite

Rental unit in Stokesley

5 out of 5 average rating, 301 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.

Guest favourite

Guest suite in North Yorkshire

4.97 out of 5 average rating, 266 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.

Guest favourite

Guest suite in Rosedale Abbey

4.99 out of 5 average rating, 169 reviews

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Guest favourite

Cottage in Yearby

4.96 out of 5 average rating, 181 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.

Guest favourite

Hut in North Yorkshire

4.98 out of 5 average rating, 244 reviews

Crumbleclive Cabin

Crumbleclive is a beautifully restored 100 year old cabin set within the dramatic backdrop of Crunkly Ghyll. It was originally the ‘Gun Room’ for the local estate in the 1890s! The Cabin has a balcony overlooking the gorge with the River Esk rapids visible at the bottom. Surrounded by Oak trees you will feel amongst the treetops as birds gather on the branches around you and fly through the gorge below. It is perfect for couples wanting a romantic getaway to recharge the batteries!

Guest favourite

Home in Guisborough

4.91 out of 5 average rating, 187 reviews

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

Guest favourite

Guest suite in Great Ayton

4.96 out of 5 average rating, 167 reviews

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.

Guest favourite

Barn in Yarm

4.99 out of 5 average rating, 272 reviews

White House Barn, near Yarm / Stockton-on-Tees

Converted single storey hay barn and coal store, this stunning property is tucked away along a private tree lined driveway and overlooks the ancient village green. Set in a peaceful village location, we are just 5 mins away from the historic market town of Yarm with it's many cafes, bars and restaurants. The Teesdale Way and River Tees are on the doorstep. Perfect location to explore North Yorkshire Moors with cities such as York, Durham and Newcastle within an hours drive.

Guest favourite

Home in Stockton-on-Tees

4.87 out of 5 average rating, 522 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.

Guest favourite

Guesthouse in North Yorkshire

4.89 out of 5 average rating, 225 reviews

Luxury 1 bedroom lodge with hot tub and fire pit

Set in the grounds of a grade 2 listed victorian gate house, cedar lodge offers modern luxury accommodation. Inside there is a double bedroom, with King size bed, shower room and living/kitchen area. Entertainment is provided by Bang and Olufsen widescreen UHDTV including streaming services. Outside is your own private patio area with a hot tub, BBQ and wood fired fire pit Great rural location for exploring hills and moors, coastline and market towns.

Guest favourite

Cottage in Stockton-on-Tees

4.86 out of 5 average rating, 148 reviews

The Old Moat Barn - With Private Hot Tub

Nestled on the outskirts of the 500-acre national woodland Coatham woods, lies The Old Moat Barn. This barn has been converted with one thing in mind: peace and relaxation. Enjoy downtime in the private courtyard, equipped with 6-seater jacuzzi, patio and seating area. Want to cabin up? Snuggle indoors or mix up the cocktail of the hour in your own exclusive bar. Whichever your preferred way to relax, The Old Moat Barn caters for all.

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Popular amenities for Middlesbrough vacation rentals

Free parking on premises

Air conditioning

Stay near Middlesbrough's top sights

Teesside Shopping13 locals recommend

Middlesbrough Institute of Modern Art (MIMA)11 locals recommend

Stewart Park9 locals recommend

Tees Barrage7 locals recommend

Tees Transporter Bridge5 locals recommend

Hollywood Bowl Stockton5 locals recommend

Other great vacation rentals in Middlesbrough

Cottage in Normanby

4.93 out of 5 average rating, 29 reviews

Cozy Farmhouse One Bedroom Cottage Near To Seaside

Guest favourite

Home in Redcar and Cleveland

4.92 out of 5 average rating, 86 reviews

Upsall Grange Farm cottage

Guest favourite

Home in Middlesbrough

4.89 out of 5 average rating, 28 reviews

House in Middlesbrough

Guest favourite

Guesthouse in Nunthorpe

5 out of 5 average rating, 55 reviews

Roseberry Loft Perfect for JCUH and Wilton Site

Guest favourite

Home in Norton

4.87 out of 5 average rating, 30 reviews

Cute and cozy village house in the heart of Norton

Guest favourite

Home in Thornaby

4.96 out of 5 average rating, 28 reviews

Beautiful Home away from home

Guest favourite

Cottage in Stockton-on-Tees

5 out of 5 average rating, 47 reviews

Riverside Mews - Yarm High Street

Guest favourite

Cottage in Yarm

4.96 out of 5 average rating, 48 reviews

Bridge Cottage

Quick stats about vacation rentals in Middlesbrough

Total rentals
290 properties
Total number of reviews
3.7K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Wifi availability
270 properties include access to wifi

Destinations to explore