Vacation rentals in Guisborough

4.88 out of 5 average rating, 602 reviews

A small outdoor balcony is illuminated by warm string lights, creating a cozy ambiance. A simple wooden table displays a candle and a bottle of champagne, with the vibrant rooftops of Whitby and the sea visible in the background under a twilight sky.

Loft in Whitby

Incredible views, Central Location, Whitby

The Crows Nest has undoubtedly one of the best views of Whitby from every window, and right in the centre of the town. A cosy loft apartment overlooking the harbour, the abbey and out to sea. Close to some amazing fish and chip shops, tearooms and everything central. A short walk to the beach.There is free on street parking with scratch cards that we provide in the W zones which are within a 5min walk from the flat. There is a pub directly opposite which at weekends you may experience some noise

Cottage in North Yorkshire

The exterior of Bancroft Cottage is highlighted by a charming entrance with wooden doors and a pitched roof. A small outdoor seating area with two chairs and a table sits on gravel, surrounded by greenery. The welcoming façade is complemented by clear blue skies.

4.99 out of 5 average rating, 160 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.

4.79 out of 5 average rating, 759 reviews

Cottage in Brotton

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

Vacation home in Harwood Dale

A wide-open landscape is shown under a clear blue sky, highlighting rolling green fields that stretch towards the horizon. Fenced areas are visible in the foreground, while distant hills and valleys can be seen further in the background.

4.96 out of 5 average rating, 112 reviews

Wykeham Cottage, Stunning Cottage in Harwood Dale

Ideal for families, couples or those looking for a quiet getaway in the middle of the picturesque North Yorkshire Moors National Park. Wykeham Cottage is a spacious self-catering cottage set in a private 150 acre estate which makes it a peaceful country retreat. The cottage is central to the local coastal towns Whitby and Scarborough which are about a 15-20 minute drive. We are also surrounded by woodland walks and the nearest beach is 6 miles away. Robin hoods bay is also only 5 miles away.

4.98 out of 5 average rating, 82 reviews

Home in Staithes

Beautifully Renovated Cottage next to Beach

Bay Tree Cottage is located in a peaceful location a stones throw away from the beach and the Cod & Lobster with the other village amenities only a short stroll away. The spacious cottage has been fully renovated throughout to a high standard. It features a wood burning stove, a great outside area and the sea views from the master bedroom are breathtaking. It is suitable for couples & families alike, ideal for both relaxing or a more energetic break, for example walking the Cleveland Way.

Cottage in Robin Hood's Bay

4.88 out of 5 average rating, 178 reviews

Cosy 2 Bed Seaside Cottage, Robin Hoods Bay Whitby

A cracking home from home, The Old Bakehouse Cottage in Sunny Place, Robin Hoods Bay, is a curl-up-with-a-book sort of place with the North Sea just round the corner crashing against the sea walls. But when the tide retreats the beach is a world of rock pools, fossil hunting and numerous coastal walks will await. Yorkshire Holiday Cottage 4 star accommodation" exceptional standard of cleanliness, décor and historic feel to the place”. Fast WIFI, Car Parking permit included. Beach 250 yards

Apartment in North Yorkshire

A narrow street features traditional buildings with a mix of storefronts and residential spaces. People can be seen walking along the cobblestone path, while chimney stacks rise above the rooftops, contributing to the charming atmosphere of the area.

4.96 out of 5 average rating, 251 reviews

17a Grape Lane, Whitby

17a Grape Lane offers the very best in holiday accommodation - a central location, a beautiful listed building, harbour views and a comfortable and stylish home from home. It’s a tasteful, luxurious and comfortable self-catering holiday apartment set out over two floors. With a huge lounge, a fitted kitchen with dining area and two generous bedrooms, two bathrooms and a downstairs toilet and fantastic harbour views, you’ll have space to really relax and enjoy your stay.

Shepherd’s hut in Goathland

A private hot tub sits under the shade of a canopy, surrounded by natural greenery. In the background, two outdoor chairs face a scenic view of rolling hills and trees, offering a tranquil setting for relaxation.

4.99 out of 5 average rating, 188 reviews

Escape into Nature - Owl

Stay in one of our two shepherds huts and enjoy the splendour of the national park. Situated alongside walking routes & the 'Rail Trail' former railway of 1836 which takes you on a wonderful adventure around the beauty of the park across rivers, streams, waterfalls & all that nature provides. We offer a piece of country life in our Shepherd huts. Ideal for those who want to escape, we are completely off the beaten track! Switch off & relax back to nature.

4.76 out of 5 average rating, 17 reviews

An outdoor area displays a private hot tub, sheltered by wooden beams. Nearby, a seating area with deck chairs is visible against a backdrop of lush greenery. The lodge's entrance is framed by tall trees, contributing to a secluded ambiance.

Cabin in Wrelton

Hot Tub Studio Lodge.

A peaceful, romantic retreat for two. Our complex features six semi-detached Studio Lodges, each with a private hot tub. (Photos show each lodge; you’ll be allocated one based on availability.) Each lodge offers an open-plan layout with a double bed, cosy living area, and fully equipped kitchen and a smart TV Step outside to your private veranda with outdoor furniture. Unwind in your hot tub under a clear night sky, the perfect way to end your day.

5 out of 5 average rating, 9 reviews

The image captures a serene beach scene at sunset, with vibrant beach huts lining the pathway. The sun is setting over the calm sea, casting warm hues across the sky. A gentle promenade extends along the water’s edge, with a grassy hill in the background.

Condo in West Cliff

Apartment West

Our newly refurbished apartment enables you to have a memorable stay in the beautiful historic seaside town of Whitby . Apartment West is situated on the West Cliff, an area hosting the popular Italian restaurant ‘Pizza West' , outdoor family activities and ‘interactive’ leisure centre Within walking distance is a bakery and coffee shops along with a good choice of bars and restaurants.

Cottage in Saltburn-by-the-Sea

An exterior view of the Mary Martin Building showcases its classic brick façade and decorative architraves. A deep blue door serves as the focal point, flanked by hanging flower baskets. A wrought iron railing lines the pathway, while the sky above is bright and partly cloudy.

4.98 out of 5 average rating, 127 reviews

Saltburn l Treetops: Sea views, Dog friendly.

Have fun with the whole family at this centrally located Saltburn property. Located in this popular coastal town, a short walk from both the town centre, Valley Gardens and beach. Created with a family friendly, stylish and relaxing holiday in mind; this property can be booked on it's own or with our second property, The Outlook. Perfect for extended family breaks (dog friendly too).

5 out of 5 average rating, 4 reviews

A hot tub is positioned on a private deck, surrounded by wooden railings. Lush trees and greenery create a natural backdrop, offering a serene view of the outdoors. A nearby lodge structure is visible in the distance, adding to the tranquil setting.

Cabin in North Yorkshire

Durham lodge North Yorkshire

Imagine stepping out onto your private patio, overlooking the majestic views of nature. You can comfortably relax on your own gorgeous patio while enjoying a glass of wine with friends and family! This spacious lodge is perfect for up to 4 people - it has a master bedroom and a twin bedroom that share a bathroom; making this place ideal for family, friends or both!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Guisborough vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Guisborough

5 out of 5 average rating, 4 reviews

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

Athelas, self catering studio

4.92 out of 5 average rating, 65 reviews

A picnic table adorned with drinks and snacks is set in a spacious outdoor area. The rustic charm of a red-brick property and a smaller wooden structure is visible in the background, framed by lush greenery and trees under a bright blue sky.

Barn in High Marishes

Hidden Family Farm Paradise- near York & the Coast

4.88 out of 5 average rating, 8 reviews

A living area features two beige sofas arranged around a light-colored rug. A small side table, a television, and a decorative mirror are also present. Black-and-white photographs adorn the walls, while a modern chandelier provides overhead lighting.

Home in Eaglescliffe

Home and away

5 out of 5 average rating, 11 reviews

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

Modern large home for families and contractors

Apartment in North Yorkshire

A view into a stylish apartment reveals a well-lit bathroom with a walk-in shower, modern fixtures, and a dark patterned floor. Adjacent is a spacious bedroom featuring a velvet bed, accented by rich wall colors and artful decor.

4.83 out of 5 average rating, 12 reviews

Gray's Getaway at Casa Del Artista - Whitby

5 out of 5 average rating, 12 reviews

A charming stone cottage entrance is framed by manicured shrubbery and trees. Two decorative dog sculptures sit on stone steps leading up to a wooden door. The pathway is lined with gravel, creating a warm and inviting approach to the home.

Home in North Yorkshire

Little Fox Cottage

4.69 out of 5 average rating, 13 reviews

A spacious bedroom features a large bed with neatly arranged linens and pillows. An elegant blue wardrobe stands prominently next to a decorative fireplace. Natural light filters through bay windows adorned with soft pink shades, while a cozy chair complements the room's color scheme.

Home in Middlesbrough

Big House, and a lot to give!