Holiday rentals in Middleham

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Top-rated holiday rentals in Middleham

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Guest favourite

Cottage in North Yorkshire

4.93 out of 5 average rating, 420 reviews

Entire Home Cozy little cottage with log burner

Cozy one bedroom Cottage with log burner; located just down the hill from Richmond Market Place. One bedroom upstairs. Kitchen, diner and lounge are all the same area with a sofa bed on the ground floor. Underfloor heating downstairs. Bedding and towels are provided for guests. Plenty of walks directly from the cottage the river being just around the corner. The castle walk is 2 minutes away. Pubs and restaurants within walking distance. Richmond has everything you need for a fabulous break.

9–16 Jan

$108 SGD per night

Guest favourite

Cottage in North Yorkshire

4.99 out of 5 average rating, 120 reviews

Bancroft Cottage: Luxury Holidays Yorkshire

Bancroft Cottage is a luxury, self-contained holiday cottage set within the grounds of Bancroft, the main house. It is a hidden jewel found within the historic Yorkshire market town of Bedale, commonly referred to as the ‘Gateway to the Dales’ The property is perfectly situated to offer guests the ease of walking to shops, restaurants and pubs via its own private access whilst being only a short ride away from the magnificent Yorkshire Dales, North York Moors, Harrogate and the city of York.

10–17 Mar

$222 SGD per night

Guest favourite

Cottage in Harmby

4.89 out of 5 average rating, 125 reviews

Puzzle Cottage Quirky Yorkshire Dales Cottage

A delightful stone-built cottage located in the village of Harmby, close to the popular Yorkshire towns of Leyburn and Middleham in the northern part of the Yorkshire Dales. Built in the 1600s, Puzzle Cottage is the oldest property in the village and is believed to have been the falconry for Bolton Castle. An unusual layout set out over three floors, the cottage has been sympathetically styled with a cosy cottage feel which adds to the immense character and charm of this historic old cottage.

3–10 Jan

$130 SGD per night

Guest favourite

Apartment in North Yorkshire

4.99 out of 5 average rating, 139 reviews

Contemporary Apartment, Richmond North Yorkshire

A stylish, modern 2 bedroom first floor apartment, with dedicated undercover parking and private access to a residents' meadow/garden, with stunning views of the River Swale and valley, yet only 5 minutes’ walk from Richmond's cobbled market place. The apartment has a full range of kitchen and laundry appliances, dishwasher, microwave oven and “Nespresso” machine. A smart television with Freesat Digital Services, and Netflix; Bluetooth/Networked/DAB/Spotify audio system; Superfast Broadband.

1–8 Oct

$197 SGD per night

Guest favourite

Cottage in North Yorkshire

4.97 out of 5 average rating, 150 reviews

A cosy cottage in the heart of the Yorkshire Dales

Primrose Cottage is a romantic retreat set within walking distance of the centre of this popular Georgian market town of Richmond in North Yorkshire. Surrounded by the stunning Yorkshire Dales, this quaint stone built cottage offers a fabulous base for two from which to explore the area. You can enjoy perusing the quirky independent shops, delicious tea rooms and wonderful pubs serving a hearty meal. The cottage offers a free parking permit throughout your stay, parking directly outside.

7–14 Feb

$160 SGD per night

Guest favourite

Farm stay in North Yorkshire

4.89 out of 5 average rating, 101 reviews

Dovecote, a modern barn conversion in the Dales.

The Dovecote is a stunning barn conversion; the perfect place to relax! Set on a traditional farm in the historical landscape of the Yorkshire Dales National Park. Unique and tranquil; The Dovecote is a perfect getaway for walkers, those who want to enjoy natural beauty or the IDA recognised Dark Sky Reserve; all from your doorstep! Your very own barn overlooking Wensleydale and the River Ure. Amazing and private; you’ll only share the idyllic Dovecote with the surrounding farm animals.

17–24 Dec

$216 SGD per night

Guest favourite

Holiday home in North Yorkshire

4.99 out of 5 average rating, 104 reviews

1 bedroom holiday home in the heart of Bedale

The Whare offers stylish, peaceful accommodation with Bedale centre close by. Fully equipped for self-catering: dishwasher, underfloor heating, wi-fi, dedicated work room, outdoor seating, parking and secure cycle storage. Ideal for a couple or a single person. No pets and no smoking. The historic market town of Bedale is 'the gateway to the Dales' and boasts a beautiful Georgian main street and an abundance of places to eat. It is the ideal base from which to explore North Yorkshire.

8–15 Jan

$149 SGD per night

Guest favourite

Cottage in Marrick, Richmond

4.99 out of 5 average rating, 205 reviews

The Barn@Graham House

Situated in the Yorkshire Dales National Park, The Barn@Graham House has far reaching views right across Swaledale and is the perfect location for guests looking for a relaxing stay. Dogs are welcome and guests enjoy their own private garden, with easy access to some lovely walks. Originally a byre, The Barn@Graham House has been lovingly restored and converted into a unique self contained 1-bedroom holiday cottage where modern facilities combine with the property’s rural heritage.

14–21 Oct

$184 SGD per night

Guest favourite

Cottage in North Yorkshire

4.99 out of 5 average rating, 188 reviews

The Barn at Cocker House in the heart of the Dales

Welcome to The Barn! Our charming 1-bedroom Cottage in Arkengarthdale offers breathtaking countryside views, perfect for couples or outdoor enthusiasts exploring the Yorkshire Dales. Immerse yourself in the beauty of rolling hills, lush fields, and meandering rivers. Take leisurely strolls or challenge yourself with hikes. The Barn provides a tranquil retreat with cozy ambiance and well-equipped amenities. Create lasting memories in this idyllic corner of Arkengarthdale.

23–30 Oct

$207 SGD per night

Guest favourite

Farm stay in North Yorkshire

4.95 out of 5 average rating, 182 reviews

1 Bedroom Annex Retreat - on a working farm

This one bedroom annex is part of a 200 year old barn conversion. Based in the Nidderdale area of outstanding natural beauty, the accommodation has its own private access and garden with seating area, internally the annex can accommodate 2 people and one friendly dog (please ensure you register your dog when booking). We are surrounded by wildlife, please look at other details for a list of birds an Ornithologist had sightings of in the month of May.

5–12 Nov

$126 SGD per night

Guest favourite

Shepherd’s hut in Stean

5.0 out of 5 average rating, 258 reviews

Luxury glamping in the Yorkshire Dales

Set in one of the most remote parts of North Yorkshire - our cosy, romantic shepherd's hut takes full advantage of its exceptional location and staggering views. Switch off and enjoy the sights and sounds of nature, including some of the most remarkable sunrises. You’ll be just off the Nidderdale Way, with breath taking walks and rides from the doorstep. We’re looking forward to making your stay as comfortable and relaxing as possible.

4–11 Feb

$135 SGD per night

Guest favourite

Guest house in Grewelthorpe

4.98 out of 5 average rating, 178 reviews

The Hutts Clocktower - at the Himalayan Garden

The Hutts Clocktower is a standalone building and perfect for 2 people - located in the award winning Himalayan Garden & Sculpture Park which is an open-air gallery home to 80+ striking contemporary sculptures, showcased in a tranquil valley setting. It covers 45 acres of stunningly beautiful woodland, gardens & an arboretum - guests will have free access (even when closed) saving equivalent of £12 pp. See Website.

26 Aug – 2 Sep

$182 SGD per night