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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 Great Ayton

4.96 out of 5 average rating, 157 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 Brotton

4.79 out of 5 average rating, 728 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.

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.

Cottage in Rosedale Abbey

4.9 out of 5 average rating, 107 reviews

Orchard House, luxury cottage retreat.

Orchard House is a cosy and well equipped self-catering property, with an amazing private hot tub. With beautiful views in a peaceful rural location overlooking ponds, streams , woodlands and fields. An ideal location for exploring the North Yorkshire moors, Whitby, Scarborough and the market towns of Malton and Helmsley and historic city of York. Sleeping up to 4 people, this cottage has everything you need for a comfortable stay. The village is a five minute walk across the fields.

Guest suite in Danby

4.77 out of 5 average rating, 253 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, 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

Cottage in Castleton Whitby

4.88 out of 5 average rating, 172 reviews

Romance or a rest at The Nest Castleton,Whitby!

Very special, cosy tiny stone cottage nestled in the North Yorkshire Moors National Park near Whitby. The Nest has a Log burner, central heating, WIFI,smart TV, Egyptian linen and twinkling fairy lights ,. Walks onto the moors from the front door , seating area outside to watch the sun go down with a large glass of wine, welcoming family pub across the road, Co-op, and fine dining pub also in the village. Train station to Whitby from the village. We welcome two dogs at the Nest.

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.

Home in Guisborough

4.98 out of 5 average rating, 61 reviews

Luxury Holiday Rental with Hot Tub!

The Paddock is two, exquisite, 4 bedroom detached self catering holiday rentals, in a private location, offering spacious modern living accommodation with large secluded outside entertaining area and hot tub! Nestled right at the foot of Guisborough Forest, on the Cleveland Hills, offering unparalleled views and access to the woods and moorland beyond, whilst still within walking distance of shops, pubs and restaurants.

Vacation home in Urra

4.96 out of 5 average rating, 117 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.

Cottage in Saltburn

4.97 out of 5 average rating, 118 reviews

Saltburn l Treetops: Sea views, Dog friendly.

Have fun with the whole family at this centrally located Saltburn property. Located in this popular coastal town, a short walk from both the town centre, Valley Gardens and beach. Created with a family friendly, stylish and relaxing holiday in mind; this property can be booked on it's own or with our second property, The Outlook. Perfect for extended family breaks (dog friendly too).

Vacation rentals for every style

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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

Home in Glaisdale

5 out of 5 average rating, 3 reviews

Athelas, self catering studio

Home in Loftus

4.88 out of 5 average rating, 40 reviews

Meadow view bungalow

Home in Stockton-on-Tees

5 out of 5 average rating, 10 reviews

Modern large home for families and contractors

Rental unit in Marton-in-Cleveland

5 out of 5 average rating, 3 reviews

Lovely independent private apartment with parking

Cabin in Great Broughton

4.95 out of 5 average rating, 60 reviews

Moor view 2 Luxury Cabin hot tub

Barn in Redcar and Cleveland

4.93 out of 5 average rating, 41 reviews

The Old Parlour - Stonecroft- Saltburn

Home in Middlesbrough

4.69 out of 5 average rating, 13 reviews

Big House, and a lot to give!

Home in Westerton

4.86 out of 5 average rating, 66 reviews

Picturesque views, sleeps 8, country living

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 vacation rentals with a dedicated workspace in Middlesbrough?
Yes! Work meets play with ease at over 120 vacation rentals in Middlesbrough featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Middlesbrough?
Four-legged friends are welcome in Middlesbrough. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Middlesbrough?
Middlesbrough has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do townhouse rentals in Middlesbrough have free parking?
Absolutely! We offer over 10 townhouse rentals with free parking in Middlesbrough. Enjoy a tailored experience with all the comforts you desire.
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.
Do townhouse rentals in Middlesbrough have a kitchen?
Absolutely! We offer over 20 townhouse rentals with a kitchen 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 Linthorpe, over 290 vacation rentals in Acklam, and over 370 vacation rentals in Coulby Newham.
What are the most popular amenities for House Rentals in Middlesbrough?
Enhance your stay in our House Rentals with the most popular amenities: over 140 homes with wifi, over 140 homes with a kitchen, over 120 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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