Holiday rentals in Oldstead

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Top-rated holiday rentals in Oldstead

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

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Top guest favourite
A stone cottage exterior is highlighted, featuring a white door and window. Pink flowering shrubs adorn the entrance. A wooden table with chairs is arranged on a stone patio, surrounded by a green fence and under a partly cloudy blue sky.
Flat in Gilling East
4.97 out of 5 average rating, 201 reviews

Fairfax View - delightful annexe cottage, Gilling

Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

Top guest favourite
The open-plan space features a spacious bed with plush bedding and two leather armchairs positioned beside a wooden dining table. Natural light enters through a window with checked curtains, creating a cozy ambiance. A flat-screen TV is mounted on the wall nearby.
Guest house in Kilburn
4.99 out of 5 average rating, 197 reviews

The Little House Peaceful & self-contained

Located in the centre of the lovely village of Kilburn on the edge of the North Yorkshire Moors National Park, the Little House is peaceful, cosy and self-contained, tucked away from the general hustle and bustle of the village with a safe garden for dogs and children. The Forresters Arms, serving local ales and meals, is a mere 20m across the square, it is best to reserve a table. The Mouseman Furniture Centre is just around the corner and the White Horse of Kilburn is a good walk up the hill.

Top guest favourite
Shepherd’s hut in West Yorkshire
4.99 out of 5 average rating, 446 reviews

Boutique Shepherd’s Hut & Alpaca Experience

Wake up in a luxury shepherd’s hut in the hills around Hebden Bridge, and start your morning feeding friendly alpacas right outside your door. Hand-crafted and thoughtfully designed, ‘The Spot’ offers a boutique countryside escape - perfect for couples looking to switch off, unwind, and enjoy something a little different. A nature retreat yet within easy reach of Hebden Bridge’s independent shops, cafes and walks, you get the best of both worlds: peaceful seclusion with lots to explore nearby.

Top guest favourite
A charming Shepherd's hut is positioned under a metal canopy, surrounded by raised wooden flower beds filled with blooming plants. The hut features bright yellow doors and windows, inviting natural light. A rustic wooden table is visible nearby, enhancing the serene outdoor setting.
Shepherd’s hut in Oldstead
5 out of 5 average rating, 107 reviews

Annie - superb lodge in exceptional Park location

A luxury shepherds hut (Plankbridge) in a stunning private location - nestled in a wildlife rich dale within a Dark Skies Reserve. With several Top 100 pubs and restaurants on the door step (Abbey Inn/Owl Hawnby/Star Inn/Black Swan) Cockerdale, near Oldstead, is an exceptional and special place. It gives you a truly immersive & tranquil experience. Walk straight from the door - or sit a while in the hot tub and enjoy the relaxing benefits of being immersed in nature - you can have it all.

Top guest favourite
The exterior of a hand-renovated railway carriage is displayed, accompanied by a private garden area featuring a fire pit, seating, and a unique egg chair. Green grass surrounds the structure, with a clear sky overhead and soft cloud formations visible in the background.
Shepherd’s hut in Norton-le-Clay
5 out of 5 average rating, 103 reviews

Railway Carriage Hideaway

A beautiful hand-renovated 1960s railway carriage, nestled in a quiet rural farm in Norton le Clay, North Yorkshire. Featuring bespoke detail throughout, our unique hideaway features a luxurious double bed with TV, a fully equipped kitchen, bathroom with shower, and a cosy log burner. Outside, enjoy the fenced private space with a fire pit/BBQ, games and seating overlooking the iconic White Horse. Tucked behind a wildflower bank with its own track and parking, this is a peaceful spot to unwind.

Top guest favourite
The exterior of a charming stone cottage is displayed, featuring a distinctive red pitched roof. Flower pots with blooming plants adorn the entrance. A well-maintained gravel pathway leads to the door, surrounded by lush greenery and shrubbery.
Home in Ampleforth
4.96 out of 5 average rating, 132 reviews

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to relax, listen to the wildlife and enjoy the beautiful countryside. The pretty market town Helmsley is less than 10 minutes drive, with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants. York is 45 mins drive and an hour to the coast for beach walks.

Top guest favourite
An open-plan living area features a spacious layout with striped bamboo flooring. A steel mezzanine platform holds a king-size bed, and the living space includes a velvet sofa and modern armchairs. Floor-to-ceiling windows allow natural light and views of the surroundings.
Home in Sutton-under-Whitestoncliffe
4.94 out of 5 average rating, 112 reviews

Stunning deluxe space, mezzanine floor, great view

About this space. Tamworth This is a stunning, stylish cottage with a steel mezzanine platform with a super king size bed. The floor to roof glass front faces West so stunning sunsets are a feature with views out to paddocks with horses and hens. Walk in shower room with door opens to black splash surround and a copper colour rainfall shower and black sink, loo and floor. Striped bamboo flooring throughout. Pitched roof with windows so when lying in bed you can see the stars at night.

Guest favourite
Hut in Coxwold
4.96 out of 5 average rating, 389 reviews

Oku Wooden Pod, Newburgh Priory Estate

Inspired by the peaceful Japanese gardens at Newburgh Priory, The Hinoki Retreat, which is set within the grounds of the Estate aims to create a truly relaxing experience that will allow you to soak away the pressures of modern day life. Your own private luxury Ofuro wood fired hot tub (2 man capacity) will be heated ready for when you arrive as a complimentary part of your stay! Oku is a luxury hand built bespoke wooden pod on a raised platform with views down to the estate grounds.

Top guest favourite
A shepherd’s hut is nestled amid tall grass in a rural setting, framed by greenery. A wooden table is set outside, featuring a breakfast spread and a fire pit nearby. In the background, a hot tub can be seen, inviting relaxation surrounded by nature.
Shepherd’s hut in Whenby
4.97 out of 5 average rating, 728 reviews

Beautiful rural shepherds hut with hot tub

This shepherds hut is in a gorgeous rural location. The hut has electricity and hot water, it will be a cosy and warm place to stay all year round. There is a recently added hot tub, to relax in and soak up the gorgeous view. A fire pit and an outdoor table, plus cooking facilities in the hut. It is in a romantic and peaceful location. We are close to Castle Howard, Yorkshire Lavender and many other wonderful places to visit. Fabulous for keen walkers and popular area for cyclists.

Top guest favourite
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.
Place to stay in Urra
4.98 out of 5 average rating, 259 reviews

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annexe 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 Annexe dates back to the 16th century and is full of charm. You can walk from our Annexe straight up onto the Cleveland way where you can walk or bike for miles. Our Annexe 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 favourite
A bottle of white wine is displayed on a table alongside a wine glass filled with the beverage. In the background, soft furnishings, including a purple armchair and light drapes, are visible, with open doors leading to a patio area.
Religious building in Thirsk
4.96 out of 5 average rating, 225 reviews

The Old Chapel: A luxury Hot Tub break

The Quaint Old Chapel is a quirky, detached historic conversion in rural Catton, Thirsk. Surrounded by stunning views, it offers endless walks, including a beautiful trail along the River Swale. Designed for pure relaxation, a luxury hot tub spa is fully included in the price. Perfect for pet lovers, the chapel features a rare, temperature-controlled dog wash to spoil your four-legged friend after a day of exploring. Includes private parking for two cars. A true North Yorkshire gem!

Top guest favourite
Three chickens of different breeds are positioned on a colorful, striped picnic table. The table features alternating pastel colors of blue, pink, and white. A green lawn and trees are visible in the background, enhancing the outdoor setting.
Cottage in Kilburn
4.93 out of 5 average rating, 340 reviews

Kilburn Chicken Cottage

Opened in 2018, dog-friendly Kilburn Chicken Cottage has been hosting guests from all over the world. With one of the highest Airbnb ratings in the area, parents and children alike have loved coming to stay to look after their own flock of hens. This 3 bedroom cottage is situated in the beautiful North Yorkshire village of Kilburn, with fast EV charging in Thirsk nearby. You're spoilt for choice when it comes to great views, great food and entertaining hens.

Popular amenities for Oldstead holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Oldstead