Holiday rentals in Middlesbrough

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Top-rated holiday rentals in Middlesbrough

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Guest favourite

Cottage in Great Ayton

4.95 out of 5 average rating, 119 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.

14–21 Feb

$113 SGD per night

Guest favourite

Flat in Stokesley

5.0 out of 5 average rating, 280 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.

10–17 Aug

$130 SGD per night

Guest favourite

Guest suite in North Yorkshire

4.97 out of 5 average rating, 217 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.

16–23 Sep

$155 SGD per night

Guest favourite

Apartment in Stokesley

4.98 out of 5 average rating, 410 reviews

Mabel Cottage

Mabel Cottage is a quiet retreat just off the High Street at the East End of the town. Situated within the conservation area, the tastefully converted outbuildings comprise an entrance hall leading to a kitchen,shower room and toilet. The living room boasts a Harrison (made in Yorkshire) king size bed, dining area and T.V . The fully equipped kitchen has fridge, microwave and hotplate. There is secure cycle storage and laundry facilities if required. There is free unlimited WiFi throughout.

4–11 Jan

$112 SGD per night

Guest favourite

Cottage in Yearby

4.96 out of 5 average rating, 160 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.

29 Sep – 6 Oct

$120 SGD per night

Guest favourite

Home in Redcar and Cleveland

4.91 out of 5 average rating, 127 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

13–20 Feb

$150 SGD per night

Guest favourite

Cabin in Middlesbrough

5.0 out of 5 average rating, 154 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.

23–30 Aug

$184 SGD per night

Guest favourite

Tiny home in Newton-on-Rawcliffe

4.98 out of 5 average rating, 191 reviews

The Hide NYM National Park Cosy Cabin with hot tub

Relaxing break for adults on the edge of the North York Moors. A 5 minute drive from Pickering, where you will find shops, bars and restaurants. York/Whitby 45 minute drive. Dalby Forest 30mins, Scarborough 40mins. A tranquil stay in a rural location. Ideal for walkers and cyclists. Includes hot tub. Contact me for discount if you would prefer not to use the hot tub Due to a balcony and limited space, The Hide is not suitable for babies, infants or children. Sorry, no pets.

10–17 Feb

$179 SGD per night

Guest favourite

Barn in Yarm

5.0 out of 5 average rating, 248 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.

2–9 Mar

$180 SGD per night

Guest favourite

Home in Stockton-on-Tees

4.88 out of 5 average rating, 463 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.

25 Nov – 2 Dec

$140 SGD per night

Guest favourite

Place to stay in Whitby, North Yorkshire

4.97 out of 5 average rating, 107 reviews

The Stable in Kildale, Whitby, North York Moors

The Stable and it’s small adjoining outbuildings once provided shelter for various animals living at the Rectory. The buildings have been carefully restored to provide a stylish and contemporary living space. The accommodation comprises of a large lounge dinner room with high ceilings and a wood burning stove. Kitchen, WC/Shower facilities and a double bedroom with amazing views. Doors from the kitchen and lounge lead to two private outdoor seating areas.

20–27 Nov

$155 SGD per night

Guest favourite

Apartment in Middlesbrough

4.9 out of 5 average rating, 107 reviews

Beautiful first floor, two bedroom apartment

Our apartment provides a spacious and comfortable base which is ideally located beside stylish bars and restaurants while also being close to the centre of town. There are excellent transport links within easy reach including the A19 and A66 taking you further afield across the north east. Inside, the apartment has a large lounge and dining room, two double bedrooms and a brand new fully equipped kitchen and bathroom.

9–16 May

$131 SGD per night