Holiday houses in Middlesbrough

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Top-rated holiday rentals in Middlesbrough

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Top Guest favourite

Home in Marton-in-Cleveland

4.95 out of 5 average rating, 113 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

Superhost

Apartment in Thornaby

4.82 out of 5 average rating, 28 reviews

Stunning Studio!

Lovingly created by our family, for yours! Our truly beautiful studio apartment in the heart of Thornaby. Just a stone's throw away from the bustling town centre, guests can enjoy an array of independent shops including bars. Whether you're seeking relaxation or a convenient and comfortable base for commuting or exploring local areas, this modern studio apartment provides a comfortable and welcoming base for your stay. Feel at home & make the most of your time in our lovely corner of the world!

Top Guest favourite

Apartment in Stokesley

5 out of 5 average rating, 327 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

Guest suite in North Yorkshire

4.98 out of 5 average rating, 313 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

Guest suite in Great Ayton

4.96 out of 5 average rating, 190 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

Home in Stockton-on-Tees

4.86 out of 5 average rating, 604 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

Tiny home in Urra

4.98 out of 5 average rating, 125 reviews

Maltkiln House Annexe 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.

Superhost

Home in Thornaby

4.89 out of 5 average rating, 183 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

Home in Redcar and Cleveland

4.91 out of 5 average rating, 111 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.

Superhost

Condo in Redcar and Cleveland

5 out of 5 average rating, 4 reviews

Flat, sleeps 2, WI-FI,Parking,Beach(Rest&Refresh)

✉ 𝗦𝗣𝗘𝗖𝗜𝗔𝗟 𝗥𝗔𝗧𝗘𝗦 𝗔𝗩𝗔𝗜𝗟𝗔𝗕𝗟𝗘 AT Rest and Refresh ✉ ★ Special Offer Available ★ Weekly/Monthly Booking For 2025 Available. 🏳 CONTRACTOR PARADISE🏳 🗝 1 Bedroom Aaprtment🗝 Sleeps Up to 2 Guests (Zip and Link Bed)🗝 Right near the city centre and the beach 🗝 Free WIFI 🗝 FREE Parking, Big Garden 🗝 Middlesborough is 10 mins away

Top Guest favourite

Cottage in Guisborough

4.94 out of 5 average rating, 222 reviews

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

Guest favourite

Guesthouse in Nunthorpe

4.98 out of 5 average rating, 86 reviews

Roseberry Loft Perfect for JCUH/ Wilton/Roseberry

Make some memories at this unique and quiet place brilliantly positioned for access to James Cook hospital and a short drive from tourist attractions areas such as Roseberry Topping and Saltburn. Positioned in old Nunthorpe, set in a private garden set back from the main house. The loft is an annexe completely separate from the main house.