Vacation rentals in Middlesbrough

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Top-rated vacation rentals in Middlesbrough

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Guest favorite
An open living area features a comfortable sectional sofa in a calming blue tone, paired with a natural wood table. Natural light enters through two skylights, illuminating the space with light neutral walls and a striped carpet providing a subtle contrast.
Home in Marton-in-Cleveland
4.95 out of 5 average rating, 126 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

Top guest favorite
A cozy sitting room is presented with a large mirror reflecting warm light from a chandelier. A television is positioned across from a log burner, surrounded by two armchairs and a comfortable sofa. Soft gray tones and decorative cushions contribute to the welcoming ambiance.
Cottage in Stokesley
4.91 out of 5 average rating, 298 reviews

Apple Tree Cottage. Stokesley.North Yorkshire.

A delightful old cottage overlooking West Green with a mix of antique, upcycled and vintage inspired decoration. The cottage is dog friendly, with a patio and large enclosed, secure garden. Located on the outskirts of the historic market town. The town has a distinguished wide cobbled high street lined with Georgian and Victorian buildings. It is served by banks,shops, up market restaurants and pubs. Surrounded by the Yorkshire Moors it makes an ideal base for exploring the Dales & East coast.

Top guest favorite
A well-lit bedroom features a spacious bed with patterned bedding, complemented by bedside lamps. A small wooden table with two chairs sits adjacent, creating a cozy dining area. Natural light streams through a skylight above, enhancing the inviting atmosphere of the room.
Condo in Stokesley
4.98 out of 5 average rating, 605 reviews

Mabel Cottage - Stay in the heart of Stokesley

This charming cottage in the heart of Stokesley is the perfect retreat, with pubs, cafes, shops, and supermarkets all within walking distance. Enjoy an equipped kitchen, shower room, a Harrison (made in Yorkshire) king size bed, dining area and T.V . Ideally located, you’re just a short drive from North York Moors National Park, Roseberry Topping, Whitby’s historic seaside charm and more. Whether exploring or unwinding, this cottage offers everything you need for a memorable Yorkshire getaway.

Guest favorite
Home in Marton-in-Cleveland
4.92 out of 5 average rating, 104 reviews

Contemporary eco home with a twist!

This stunning 2 bedroom eco home is finished to a very high standard throughout with many custom features and bespoke finishes. This home is truly a home for the future and is exceptionally eco-friendly with an air source heat pump (ASHP) providing underfloor heating throughout and a Mechanical Ventilation Heat Recovery (MVHR) system with built in pollen filters for extra warmth in the winter and a cool breeze in the summer. This unique property also benefits from a relaxing 4x6m mezzanine.

Top guest favorite
A self-contained studio apartment features a spacious bed with light blue bedding. A dining table with black chairs is positioned near a window that offers views of the countryside. The well-equipped kitchen is visible, with modern appliances and counter space.
Apartment in Stokesley
5 out of 5 average rating, 337 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 favorite
A charming building features wooden siding and large windows that illuminate the interior. Surrounding the structure is a well-kept garden with diverse greenery and pathways, enhancing the outdoor ambiance. The picturesque setting is complemented by a stone patio area for sitting and relaxing.
Guest suite in North Yorkshire
4.98 out of 5 average rating, 349 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.

Superhost
The exterior of a charming cottage is visible, featuring natural stone walls and a blue front door. Bay windows are present, complemented by shutters. A flower pot hangs by the door, adding a touch of greenery. Adjacent properties are visible, showcasing a cozy neighborhood ambiance.
Home in Guisborough
4.85 out of 5 average rating, 310 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

Top guest favorite
Barn in Moorsholm
4.97 out of 5 average rating, 105 reviews

Hillock's Farm Cottage, luxury

Welcome to our outstanding luxury holiday cottage nestled in the charming village of Moorsholm, Cleveland. This outstanding barn conversion offers a serene escape for couples seeking tranquility and comfort. As you step into this exquisite retreat, you're greeted by the spaciousness of the open plan layout, featuring a magnificent fully equipped kitchen, dining area, and beautiful living room with large fire place. The expansive design creates a sense of freedom and relaxation.

Top guest favorite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny home in Urra
4.98 out of 5 average rating, 197 reviews

Maltkiln House Annexe North Yorkshire moors

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. We are also very close to some great pubs and restaurants.

Top guest favorite
A wooden lodge is depicted, featuring a spacious deck enclosed by a low fence. Outdoor seating arrangements are visible on the deck, with greenery surrounding the lodge. Large windows reflect natural light, enhancing the rustic charm of the structure set against a backdrop of hills.
Cabin in Middlesbrough
4.99 out of 5 average rating, 184 reviews

The Lodge at Viewley Hill Farm

Viewley Hill Farm Lodge is a spacious and comfortable 3 bedroomed wooden lodge on a working farm. Situated in a peaceful and idyllic setting, the lodge has stunning views of the North York Moors and the Cleveland Hills. Guests can enjoy a range of walks in the local area including some that can be accessed directly from the farm. The local area boasts not only fabulous countryside but also easy access to the glorious north east coast and a wide variety of visitors attractions.

Top guest favorite
A charming brick structure is featured with a pitched roof and dormer windows. A small patio area is presented with two potted shrubs and a circular table set with two chairs. Double doors open to the inviting entrance, enhancing the warm exterior.
Barn in Yarm
4.99 out of 5 average rating, 302 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.

Superhost
The exterior of a modern two-bedroom house is showcased, featuring a spacious roof terrace and large windows framed by greenery. The brick facade is complemented by bicycles parked near the entrance, with garage doors visible to the right.
Home in Stockton-on-Tees
4.86 out of 5 average rating, 653 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.

Popular amenities for Middlesbrough vacation rentals

When is the best time to visit Middlesbrough?

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Avg. priceG$18,823 GYDG$18,196 GYDG$18,823 GYDG$19,660 GYDG$17,987 GYDG$18,823 GYDG$20,496 GYDG$20,287 GYDG$19,660 GYDG$20,078 GYDG$19,032 GYDG$20,706 GYD
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Frequently Asked Questions

  • What are the best places to stay in Middlesbrough?

    Central Middlesbrough has many apartments and period homes near the town’s lively dining and culture spots. Stays around Linthorpe Road and Albert Park are frequently suggested for easy access to shops, green spaces, and locally rooted restaurants.

  • What are the best things to do in Middlesbrough with kids?

    Families often explore Stewart Park’s playgrounds and gardens, enjoy hands-on science at the local museum, or spend the day at Dorman Museum with interactive exhibits. The area also has soft play centres and community swimming pools.

  • What are some of the best things to do in Middlesbrough?

    Explore modern and historic art at MIMA, stroll through Stewart Park’s green space, or discover local history at Dorman Museum. Riverside Stadium draws football fans, while the Transporter Bridge has sweeping views of the area.

  • How is the weather in Middlesbrough?

    Middlesbrough has cool winters around 34–46°F (1–8°C) and mild summers reaching up to 70°F (21°C). Rainfall is spread throughout the year, so pack a light waterproof layer along with comfortable shoes.

  • When is the best time to visit Middlesbrough?

    Late spring through early autumn is often recommended, when temperatures are milder and local parks are especially welcoming. Events and festivals also add a lively atmosphere during these months.

  • What are the best places to visit in Middlesbrough?

    MIDDLESBROUGH Institute of Modern Art (MIMA) is known for contemporary exhibitions, while Dorman Museum explores the region’s past. The Transporter Bridge and Stewart Park are often recommended for distinctive local character.

  • What are some hiking trails in Middlesbrough?

    Stewart Park has gentle paths through meadows and woodlands, while Flatts Lane Woodland Country Park is often suggested for peaceful forest walks. Nature lovers also explore trails near the Tees River and wooded areas around Middlesbrough.

  • What are some family activities we can do in Middlesbrough?

    Visit Dorman Museum for interactive exhibits, explore Stewart Park’s gardens and animal enclosures, or discover hands-on learning at the local science centre. Splash around at a community pool or try indoor climbing for active fun.

  • What are some of the best day trip ideas from Middlesbrough?

    Explore nearby coastal villages for fresh air and local seafood, visit the North York Moors National Park for scenic walks, or discover historic market towns in the region. Castles and seaside promenades also draw day visitors from Middlesbrough.

  • Are there any pet friendly accommodations available in Middlesbrough?

    Many accommodations in Middlesbrough welcome pets, especially in residential neighborhoods and near local parks. Look for homes or apartments with outdoor areas or easy access to walking paths.

  • What are some local tips for visiting Middlesbrough?

    Middlesbrough’s cultural spots often blend art, history, and locally rooted events—check community listings for exhibitions and performances. Pack layers for changeable weather, and try strolling around the Linthorpe and Albert Park areas for independent shops and cafés.

  • What is Middlesbrough known for?

    Middlesbrough has an industrial heritage, especially in steel and shipping, and is recognized for landmarks like the Transporter Bridge. The town is also known for its role in the local football community and vibrant arts scene at MIMA.

  • What are the best hidden gems to explore in Middlesbrough?

    Artisan cafés and vintage shops around Baker Street and Bedford Street are locally popular for creative finds. The Captain Cook Birthplace Museum in Stewart Park and the green spaces along the Tees River offer quieter escapes.

  • What are the best foods to try in Middlesbrough?

    Parmo, a breaded cutlet with béchamel sauce and cheese, is a local favorite often suggested for visitors. Middlesbrough’s food scene also features South Asian curries, Mediterranean dishes, and traditional British bakeries.

  • What should I bring for a trip to Middlesbrough?

    Pack a waterproof jacket and layers, as weather can shift from cool to mild throughout the year. Comfortable shoes are useful for city walks, and a camera is handy for the area’s historic sites and green spaces.

  • What is the nightlife in Middlesbrough like?

    Middlesbrough’s nightlife has lively pubs, bars with live music, and energetic venues around Linthorpe Road and Baker Street. The town’s clubs and student nights are often popular, especially during the university term.

  • What are the most popular events or festivals in Middlesbrough?

    Middlesbrough frequently hosts live music events, multicultural festivals, and the Mela, a celebration of South Asian heritage. Art trails, food fairs, and football matches at Riverside Stadium are also community highlights throughout the year.

  • Are there family friendly vacation rentals in Middlesbrough?

    Many vacation rentals in Middlesbrough are suited to families, especially homes and apartments near green spaces or leisure facilities. Look for places with multiple bedrooms or outdoor areas for extra comfort.

Quick stats about vacation rentals in Middlesbrough

  • Total vacation rentals

    Explore 360 vacation rentals in Middlesbrough

  • Nightly prices starting at

    Middlesbrough vacation rentals start at G$4,183 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Middlesbrough vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middlesbrough rentals

  • 4.6 Average rating

    Middlesbrough stays receive an average rating of 4.6 out of 5 from guests

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