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Middlesbrough vacation rentals

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Top-rated vacation rentals in Middlesbrough

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

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Cottage in Great Ayton

4.96 out of 5 average rating, 158 reviews

Cliff Ridge Cottage

Great Ayton is a pretty village & is right on the edge of the North York Moors, a great location for walking, cycling & mountain biking. Garden with patio has seating outside or undercover in the "outhouse". The cottage has street parking, but parking directly outside of the cottage isn’t always possible. The coast is a 20 minute drive away. The Village has several quality bars & restaurants, & take away food options. All are a safe 5 minute walk. The property has secure storage for bikes.

Cottage in North Yorkshire

4.99 out of 5 average rating, 151 reviews

Bancroft Cottage: Luxury Holidays Yorkshire

Bancroft Cottage is a luxury, self-contained holiday cottage set within the grounds of Bancroft, the main house. It is a hidden jewel found within the historic Yorkshire market town of Bedale, commonly referred to as the ‘Gateway to the Dales’ The property is perfectly situated to offer guests the ease of walking to shops, restaurants and pubs via its own private access whilst being only a short ride away from the magnificent Yorkshire Dales, North York Moors, Harrogate and the city of York.

Cottage in Brotton

4.79 out of 5 average rating, 735 reviews

Listers Lodge

Pre 1800's cottage full of character located in a conservation area. Central to the highly recommended Saltburn, Staithes & Guisborough: steeped in history with fantastic beaches. Take National Trust walks over cliffs, woodlands,Moors & Cleveland Way. Located on main bus routes and short walk from pubs, restaurants & parks. Dogs welcome at £25 charge earlier/late check in or out times possible on occasions/request. Driveway parking not suitable for large cars-no issue for off street parking

Cottage in Skelton-in-Cleveland

4.95 out of 5 average rating, 133 reviews

Sundial Cottage, Stunning 3Bed Cottage with Hottub

Relax with the whole family or friends at Sundial cottage. Jump in the Hot tub, enjoy the open plan kitchen and lounge along with three spacious bedrooms. Fibre WiFi. Based in a small quiet village, we ask all our quests to respect our neighbours when outside and we do not accept stag/hens. Perfect for walks in the North Yorkshire moors, or staying in catching up with friends or family. Well behaved Pets are welcome at the cottage and there is private parking spaces for your convenience.

Home in Richmond

4.99 out of 5 average rating, 102 reviews

Treetops Cottage @ Treetops Hideouts

Treetops Cottage is a luxury country retreat just one mile from bustling Richmond nestled in a private, stunning setting. The newly refurbished property boasts exceptional far reaching views across the rolling countryside and the south facing patio is a fantastic space to watch the wild deer that come up from Sandy Beck. Ideally located alongside Brokes giving direct access to the beautiful surrounding countryside, the property offers luxury living with great days out on your doorstep.

Cottage in Yearby

4.96 out of 5 average rating, 183 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 suite in Danby

4.78 out of 5 average rating, 254 reviews

Holly Cottage in Danby on North York Moors

Welcome to our characterful historic 500-year-old cosy cottage with views of North York Moors, set in a moorland village near a wonderful bakery, pub, station, and shop. Ideal for a quiet retreat and relaxing breaks. Country garden. Moorland walks from the door. The recent renovation has made a spacious light space with an upstairs bedroom and mezzanine and a large airy, sitting room. Shower room.Sleeps 4. Oak beams and feature stone wall. Pottery, walking, and foraging are available

Home in Guisborough

4.91 out of 5 average rating, 194 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

Shepherd’s hut in Goathland

4.99 out of 5 average rating, 179 reviews

Escape into Nature - Owl

Stay in one of our two shepherds huts this Autumn and enjoy the splendour of the national park. Situated alongside walking routes & the 'Rail Trail' former railway of 1836 which takes you on a wonderful adventure around the beauty of the park across rivers, streams, waterfalls & all that nature provides. We offer a piece of country life in our Shepherd huts. Ideal for those who want to escape, we are completely off the beaten track! Switch off & relax back to nature.

Cottage in Staithes

4.99 out of 5 average rating, 111 reviews

Saltwater-Beautiful, cosy old fisherman's cottage

Previously a fisherman’s cottage in the quaint seaside village of Staithes. A stones throw from the harbour, Saltwater cottage has been fully renovated throughout to the highest standard. With a log burner, beams galore and a beautiful high spec kitchen with Belfast sink. It is the perfect hideaway to escape the stresses of daily life, waking up to glimpses of the glistening sea and losing yourself in the sound of crashing waves and soaring seagulls.

Cottage in Stockton-on-Tees

4.86 out of 5 average rating, 160 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.

Vacation home in Urra

4.96 out of 5 average rating, 118 reviews

Bluebells Cottage, Chop Gate, North Yorkshire.

Luxury romantic Yorkshire cottage retreat in the North Yorkshire Moors National Park nestled next to a bluebell wood with a babbling brook and direct access out into the most beautiful countryside. Close to the beautiful historic market towns of Helmsley and Stokesley and 10 minutes from James Cook's village of Great Ayton. Day trip distance to the seaside fishing villages of Whitby, Staithes and Robin Hoods bay.

Vacation rentals for every style

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Popular amenities for Middlesbrough vacation rentals

Laptop-friendly workspace

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

Home in Glaisdale

5 out of 5 average rating, 3 reviews

Athelas, self catering studio

Home in Hartlepool

4.98 out of 5 average rating, 51 reviews

Beautiful two bedroom townhouse

Home in Stockton-on-Tees

5 out of 5 average rating, 11 reviews

Modern large home for families and contractors

Apartment in Marton-in-Cleveland

5 out of 5 average rating, 4 reviews

Lovely independent private apartment with parking

Cottage in Rosedale Abbey

4.88 out of 5 average rating, 110 reviews

Orchard House, luxury cottage retreat.

Home in Middlesbrough

4.69 out of 5 average rating, 13 reviews

Big House, and a lot to give!

Cabin in Witton-le-Wear

5 out of 5 average rating, 17 reviews

Maple Pod at Chapman Hill Farm

Home in Tow Law

4.93 out of 5 average rating, 108 reviews

Large countryside home

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

Frequently Asked Questions

Are there townhouse rentals with a dedicated workspace in Middlesbrough?
Yes! Work meets play with ease at over 10 townhouse rentals in Middlesbrough featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly apartment rentals in Middlesbrough?
Four-legged friends are welcome in Middlesbrough. Choose from more than 10 apartment rentals for guests traveling with pets.
Are there family-friendly house rentals in Middlesbrough?
Middlesbrough has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in Middlesbrough have wifi?
Absolutely! We offer over 10 hotel rentals with wifi in Middlesbrough. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Middlesbrough?
Make yourself at home in Middlesbrough by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in Acklam, over 290 vacation rentals in Linthorpe, and over 370 vacation rentals in Coulby Newham.
How much does it cost to stay in serviced apartment rentals in Middlesbrough?
Experience the best of Middlesbrough with our serviced apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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