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Middlesbrough vacation rentals

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Top-rated vacation rentals in Middlesbrough

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A winding path is visible leading towards a prominent hill topped with vegetation. Lush green fields extend on either side, framed by a wooden fence. The sky is clear, with a few wispy clouds, suggesting a pleasant day in the North York Moors.

Cottage in Great Ayton

4.96 out of 5 average rating, 160 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.

A wooden pier extends over the water, bordered by black wrought-iron benches. The backdrop features a grassy hill with charming buildings atop, under a dramatic sky filled with soft, colorful clouds. The calm water reflects the pier's structure, enhancing the serene atmosphere.

4.79 out of 5 average rating, 210 reviews

Private one bedroom home in Saltburn

A unique and quirky property owned and lovingly restored by a family with a love of the local area and a passion for providing a home from home environment for their guests. Property features a lounge and kitchen dining room downstairs, a bedroom on the first floor and a bathroom and separate dressing room on the third floor. Décor is light and airy with Voyage Maison fabrics. Fantastic restaurants and bars within easy walking distance. Beach and train station a short stroll from your front door

Cottage in Brotton

4.79 out of 5 average rating, 746 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

The exterior of Sundial Cottage is presented at dusk, showcasing a charming two-story structure with a welcoming front porch and multiple windows. A spacious brick pathway leads to the entrance, while the surrounding areas feature subtle landscaping and outdoor lighting, enhancing the cozy appearance.

Cottage in Skelton-in-Cleveland

4.95 out of 5 average rating, 138 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.

A charming kitchen area features a log burner set within a stone wall. A wooden dining table is paired with a classic chair. Shelves and cabinets display dishware and cooking essentials, while natural light enhances the warm atmosphere.

4.89 out of 5 average rating, 179 reviews

Romance or a rest at The Nest Castleton,Whitby!

Very special, cosy, really 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.

A south-facing patio area features a relaxing hot tub in the foreground, with a cozy seating arrangement of dark wicker chairs and a small table. Nearby, a gas barbecue stands ready, complemented by well-tended flower beds and panoramic views of the rolling countryside.

4.99 out of 5 average rating, 107 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.

The entrance of the cottage features a white door marked with the number '22'. Flanking the door, two potted topiary plants rest on either side. A welcome mat lies on the stone step, and a nameplate is affixed beside the door, adding charm to the inviting entryway.

Cottage in Yearby

4.96 out of 5 average rating, 185 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.

The exterior of Orchard House is framed by lush green foliage, highlighting the natural surroundings. The stone structure features multiple windows and a distinctive roof, blending harmoniously with the peaceful rural landscape. Sunlight filters through the leaves, creating a serene atmosphere.

Cottage in Rosedale Abbey

4.88 out of 5 average rating, 115 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.

An open living space features original oak beams and a mezzanine with a double bed. An inviting seating area includes a red armchair and a wooden table with chairs. Soft lighting highlights a plush rug on the wooden floor, while a window allows natural light to enter.

Guest suite in Danby

4.78 out of 5 average rating, 255 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

A dining area features a wooden table set for an intimate meal, surrounded by upholstered chairs. A warm wood-burning stove is visible, with a television mounted on the wall nearby. Light floods the space through windows, enhancing the inviting setting.

Home in Guisborough

4.89 out of 5 average rating, 213 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

4.86 out of 5 average rating, 170 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.

A stone terrace area is visible with slate flooring, featuring outdoor seating arrangements. The rustic cottage has a red-tiled roof and multiple windows, allowing natural light to enter. Lush green grass surrounds the space, complemented by the sight of trees in the background.

Vacation home in Urra

4.96 out of 5 average rating, 119 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

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

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A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

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

The exterior showcases a stone-clad building with a warm wooden door featuring a decorative wreath. Window shutters complement the charming facade, and the roof is finished with traditional tiles. A gravel pathway leads to the entrance, enhancing the welcoming ambiance of the secluded retreat.

Home in Glaisdale

5 out of 5 average rating, 3 reviews

Athelas, self catering studio

A comfortable outdoor seating area is displayed, featuring a wicker sofa adorned with decorative pillows. A glass-topped table sits beside a potted plant, offering a clear view of the sea in the background. Bright yellow gorse flowers add color to the landscape.

Camper/RV in Blackhall Colliery

4.86 out of 5 average rating, 21 reviews

Seaview Retreat Crimdon Dene

A decorative tray is arranged on a bed, featuring a lantern, a candle, and small vases with neutral-toned flowers. Soft linens are displayed on the bed, with natural light filtering through sheer curtains, creating a serene and calming atmosphere.

Home in Stockton-on-Tees

5 out of 5 average rating, 11 reviews

Modern large home for families and contractors

A modern bathroom features sleek marble walls, with a walk-in shower beside a circular sink. A single window allows natural light to brighten the space. A gray shower curtain and a yellow towel add color, while a large ceiling light illuminates the area.

Apartment in Marton-in-Cleveland

5 out of 5 average rating, 5 reviews

Lovely independent private apartment with parking

4.69 out of 5 average rating, 13 reviews

Big House, and a lot to give!

The open-plan living area features a modern kitchen with sleek cabinetry and a cozy sofa positioned by large glass doors. These doors lead to a private deck, showcasing expansive valley views. A dining set is visible on the deck, ideal for enjoying meals outdoors.

Cabin in Witton-le-Wear

5 out of 5 average rating, 22 reviews

Maple Pod at Chapman Hill Farm

Home in Tow Law

4.93 out of 5 average rating, 111 reviews

Large countryside home

An open-plan living area is presented, featuring a cozy seating arrangement with a grey sofa and a small dining table. Large windows allow natural light to fill the room, while a stylish fireplace and modern kitchen amenities are also visible.

Condo in North Yorkshire

4.78 out of 5 average rating, 9 reviews

Georgia, Queens Road, 2 Bed, central location

Quick stats about vacation rentals in Middlesbrough

Total rentals
320 properties
Total number of reviews
4K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Wifi availability
300 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 apartment rentals in Middlesbrough?
Middlesbrough has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do hotel rentals in Middlesbrough have wifi?
Absolutely! We offer over 20 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 320 vacation rentals in Linthorpe, over 320 vacation rentals in Acklam, and over 390 vacation rentals in Coulby Newham.
How much does it cost to stay in apartment rentals in Middlesbrough?
Experience the best of Middlesbrough with our apartment rentals, starting at about $20 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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