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Cottage vacation rentals in Guisborough

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Quick stats about cottage rentals in Guisborough

  • Nightly prices starting at

    Guisborough vacation rentals start at G$18,828Β GYD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guisborough rentals

  • 4.9 Average rating

    Guisborough stays are highly rated by guestsβ€”averaging 4.9 out of 5!

Top-rated cottage rentals in Guisborough

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

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Top guest favorite
The stone cottage exterior showcases charming details, including a wooden door painted in soft blue. Flower pots filled with pink and white blooms adorn the entrance, enhancing the inviting appeal of the home. A small window is framed by additional greenery.
Cottage in Castleton

Cheerful & Quaint 18th Century cottage

Pretty cottage situated on the village green in the heart of Castleton village. Open fire for creating a cosy night in & perfect for exploring the beautiful North Yorkshire Moors. Castleton is lucky to have two great pubs The Downe Arms with fabulous food and atmosphere right across the road and The Eskdale which serves lovely β€˜fine dining food’ but also lovely just for a drink. There’s the Old Chapel Tearoom, a Londis & β€˜Off the Scale’ shop We are also along the Esk Valley train line to Whitby

4.96 out of 5 average rating, 293 reviews
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

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.

4.91 out of 5 average rating, 330 reviews
Guest favorite
The exterior of Sundial Cottage is presented at dusk, showcasing a charming two-story structure with a welcoming front porch and multiple windows. A spacious brick pathway leads to the entrance, while the surrounding areas feature subtle landscaping and outdoor lighting, enhancing the cozy appearance.
Cottage in Skelton-in-Cleveland

Sundial Cottage, Stunning 3Bed Cottage with Hottub

New Prices Enforced by Airbnb include 15.5% fee to Airbnb. Relax with the whole family or friends at Sundial cottage. Covered Hottub, enjoy the open-plan kitchen, lounge along with three spacious bedrooms. Fibre WiFi. Based in a quiet village, we ask all our quests to respect our neighbours when outside and we do not accept stag/hens. Perfect for walks in the North Yorkshire moors, or catching up with friends or family. Well behaved Pets are welcome at the cottage and there is 2 parking spaces

4.94 out of 5 average rating, 178 reviews
Top guest favorite
An open dining area is filled with natural light from skylights and large windows. A table set for dining is surrounded by several light-colored chairs. A view of a private deck can be seen through the patio doors, accompanied by vibrant floral arrangements on the table.
Cottage in Commondale

Winnow Cottage . in the Heart of the NY Moors

Winnow Cottage is set in the idyllic North York Moors National Park. Dating back to the 1800s, the cottage has an open plan living and dining area with a kitchen and two en-suite double bedrooms. Patio doors lead out to a private decked area with views of the moors. The cottage is dog-friendly, 2 dogs welcome and accessed via a 1/4 mile rough single bridle track. There are many walking and cycling routes from the cottage and it is well-situated for exploring beautiful North Yorkshire.

4.94 out of 5 average rating, 161 reviews
Top guest favorite
The exterior of Hillfoot Cottage is framed by lush greenery and trees, providing a sense of privacy. The white cottage features a welcoming front door and two windows, complemented by a well-maintained garden area with hedges and a wooden gate marking the entrance.
Cottage in Redcar and Cleveland

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.

4.96 out of 5 average rating, 210 reviews
Top guest favorite
A living area features a comfortable couch adorned with decorative pillows and a single armchair beside a bright window. A simple coffee table rests on a textured rug, completing the cozy ambiance of the space.
Cottage in Great Ayton

Bumble Cottage. Lovely 2 bedroom Edwardian cottage

Bumble cottage is a beautiful family and dog friendly holiday home. Only a short walk from the centre of the village. Great Ayton is situated on the edge of the North Yorkshire moors and provides a wonderful base for exploring the local area. There are many possibilities for family activities, for walking, hiking, road and mountain biking and running. The beautiful beach at Saltburn is also only a 15 minute drive away. There are several excellent and unique cafes, restaurants and bars.

4.98 out of 5 average rating, 118 reviews
Superhost
The exterior view of the cottage features a blend of brick and white-painted surfaces. Large windows provide ample natural light. A front door, highlighted with decorative features, is flanked by planters. The quiet street showcases marked paving and distinct yellow lines.
Cottage in Guisborough

Cosy, 2 Bedroom Cottage in Guisborough Town Centre

A cosy cottage in the heart of Guisborough town centre with easy access to local shops and a large supermarket minutes away. The property is the ideal location for exploring North Yorkshire. 15 to 30 mins from the North Yorkshire Moors, Redcar and Saltburn beaches, Roseberry topping and Whitby. It’s ideal for family breaks, mini breaks and perfect for walkers. A free 2 hour high street parking disk is provided, plus free parking 6pm till 8am daily. Other times up to Β£4 a day.

4.83 out of 5 average rating, 311 reviews
Top guest favorite
Cottage in Stokesley

Townhouse in Stokesley

A delightfully old, mid-terraced townhouse situated in the conservation area of West Green, Stokesley. The house has been sympathetically decorated and furnished to reflect its heritage, with a beautiful collection of traditional, upcycled and vintage inspired furniture to support independent, local businesses. We are dog friendly. Outside we have a secure, seated courtyard. Stokesley and the local area hosts all manner of restaurants and cafes, many of which are dog-friendly.

4.98 out of 5 average rating, 124 reviews
Guest favorite
The exterior of the cottage features a welcoming entrance with a decorative awning. A small courtyard is highlighted by a table and chairs, ideal for outdoor dining. Sunlight streams down, illuminating the surrounding greenery and flower pots, creating a serene outdoor space.
Cottage in Saltburn Marske and New Marske

Cosy Seaside Cottage

Enjoy a memorable visit when you stay in this unique , stylish cosy cottage. Just 100 meters from the dog friendly sandy beach with breathtaking views . Walk to Saltburn to explore the many restaurants and bars or stay local with many coffee shops , bars , places to eat and shops to visit . When you are not exploring the local area , of walking many of the excellent trails you can sit and enjoy a glass or two on one of the two large comfy sofas in front of a real fire.

4.9 out of 5 average rating, 143 reviews
Guest favorite
A cozy living room is presented, featuring a light gray sofa with decorative pillows. An exposed brick fireplace is situated beside the sofa, housing a small stove. Natural light enters through a window with adjustable shutters, highlighting the subtle tones of the area rug.
Cottage in Loftus

Griff Cottage, luxury holiday cottage Skinningrove

Griff Cottage is located in Skinningrove on the North Yorkshire coast, stay local and enjoy the two fantastic beaches or use the cottage as a base to explore the beautiful coastline and the North Yorkshire Moors. Just a few hundred yards from the Cleveland Way and short walk to the local pub serving food. The cottage has been fully refurbished and is maintained to a very high standard and every effort has made to ensure your stay with us is as perfect as possible.

4.99 out of 5 average rating, 220 reviews
Top guest favorite
The exterior of the building is showcased, featuring stone walls and a traditional red tile roof. Windows are framed in white, reflecting a classic style. A small bench is visible near the entrance, and a stone wall borders the pathway leading to the welcoming entrance.
Cottage in Danby

Farm Cottage with Stunning Views.

Nestled in the heart of the North Yorkshire Moors on our 100 acre Jacob Sheep Farm, close to the villages of Danby (3.9 miles) and (Castleton 3.7 miles) We are nothing like a hotel but instead offer quirky, comfortable, open plan, home from home accommodation in a tranquil setting. Arriving on foot, it is fully equipped with everything you might need. Close to Danby Castle wedding venue. We welcome all family pets and have plenty of fields for off lead exercise.

4.99 out of 5 average rating, 586 reviews
Guest favorite
The charming cottage exterior features a stone facade with a mix of traditional wooden windows and a white front door. A manicured lawn is visible in front, surrounded by lush greenery and a hint of floral elements, inviting guests to explore the character within.
Cottage in Brotton

Listers Lodge

Pre 1800's cottage full of character. 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 Β£25 charge earlier/late check in or out times possible on occasions/request. Driveway parking also plenty off street parking

4.79 out of 5 average rating, 889 reviews

Popular amenities for Guisborough cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favorite
The front view of a charming stone cottage features a well-maintained grassy area and parking space. Clear blue skies are visible above, highlighting the rustic architecture. The property name, 'Rambling Rose,' is displayed on gently weathered signage near the parking area.
Cottage in Loftus

Rambling Rose Cottage, near Staithes

4.92 out of 5 average rating, 253 reviews
Top guest favorite
A well-appointed kitchen space features wooden beams overhead, with a range of cabinetry and modern appliances. A dining table is set for four, adorned with plates, glasses, and a vase of flowers, creating a welcoming atmosphere for meals.
Cottage in Stape

Meadows Edge, hot tub Pet friendly , fishing

4.98 out of 5 average rating, 108 reviews
Top guest favorite
Cottage in Loftus

The Byre @ Low Waupley Farm with HOT TUB

5.0 out of 5 average rating, 96 reviews
Top guest favorite
A cozy sitting area features a red sofa and a yellow couch, complemented by a rustic coffee table. A log burner stands in the corner, surrounded by natural stone walls. Behind, an open kitchen area is visible, enhancing the spacious layout.
Cottage in Hinderwell

Boulby Grange Byre Cottage

5.0 out of 5 average rating, 57 reviews
Superhost
Cottage in Skelton-in-Cleveland

Coastal Hot Tub & Sauna Retreat, Sleeps 2-8, Views

4.9 out of 5 average rating, 31 reviews
Superhost
A vibrant lounge area features stylish orange sofas contrasting against an exposed stone wall. A sleek coffee table made of silver-toned metal sits at the center, complemented by wooden shelves displaying decorative items. A flat-screen television is mounted on the wall, adding modern convenience.
Cottage in Guisborough

The Nook, luxury cottage, dog welcome and hot tub

A single-story barn conversion is showcased, featuring a charming mix of stone and brick exteriors. Large windows allow natural light to illuminate the interior, while a green door adds a pop of color. A gravel path leads to the entrance, surrounded by a peaceful countryside setting.
Cottage in Stockton-on-Tees

The Old Moat Barn - With Private Hot Tub

4.82 out of 5 average rating, 253 reviews
Guest favorite
An outdoor dining area is presented under a wooden structure. A large table is set with blue plates, glasses, and a coffee pot. A vase of fresh roses adds color, while a cozy chimenea stands nearby. Lush greenery and distant fields create a serene backdrop.
Cottage in Rosedale Abbey

Oak house

4.88 out of 5 average rating, 168 reviews

Pet-friendly cottage rentals

Top guest favorite
An outdoor area features a stone-paved patio with a wooden picnic table, surrounded by planters holding blooming flowers. A white door is visible, leading to the property, alongside wall-mounted lanterns and decorative hanging baskets.
Cottage in Loftus

Wheelhouse,Grinklebell Cottage

4.95 out of 5 average rating, 189 reviews
Guest favorite
A charming stone cottage is displayed, featuring a symmetrical facade with two prominent windows and a white door. Accents such as a front garden with flowers and a small fence create a welcoming entrance. The surroundings include lush greenery and nearby trees.
Cottage in Castleton Whitby

Romance or a rest at The Nest Castleton,Whitby!

4.92 out of 5 average rating, 251 reviews
Top guest favorite
A spacious bedroom features a large bed with neatly arranged linens and towels. Two bedside tables flank the bed, each fitted with wall-mounted lamps. A mirror stands beside a shelf displaying books. Natural light streams in from a nearby window.
Cottage in Great Ayton

Spacious barn conversion in North Yorkshire

4.96 out of 5 average rating, 379 reviews
Top guest favorite
A stone bench is positioned on a grassy hillside, offering a panoramic view of rolling green valleys and distant hills under a partly cloudy sky. The landscape features patches of heather and a serene atmosphere, inviting moments of quiet reflection.
Cottage in Glaisdale

NY Moors' peaceful retreat - Great Fryup, Lealholm

4.89 out of 5 average rating, 400 reviews
Guest favorite
The image depicts historic ruins atop a grassy hill, with arched stone structures prominently featured. A lone tower stands nearby, under a clear sky that hints at a serene atmosphere. Surrounding fields and a tree are visible in the foreground.
Cottage in Rosedale Abbey

Florence Terrace

4.84 out of 5 average rating, 194 reviews
Guest favorite
A spacious living area features a comfortable beige sofa facing a large wall-mounted television. Exposed wooden beams add character to the ceiling. A soft glow is provided by a round ceiling light, while a small window allows natural light to brighten the room.
Cottage in Yarm

Bridge Cottage

4.94 out of 5 average rating, 100 reviews
Guest favorite
An open plan living area features leather sofas facing a log burner. Exposed brick walls add character to the space. A staircase leads to the kitchen, which is equipped with modern amenities. A smart TV and a cozy rug contribute to the inviting atmosphere.
Cottage in Hinderwell

The Old Tap Room. Your cosy escape. Dog friendly

4.93 out of 5 average rating, 107 reviews
Guest favorite
The exterior of a charming Grade II listed cottage showcases a stone facade with a traditional red-tiled roof. A terrace area is visible, featuring gravel and a set of outdoor furniture. Green accents highlight the door and windows, enhancing the rural setting.
Cottage in Loftus

Shrubberies Cottage is a charming place to stay

4.87 out of 5 average rating, 141 reviews

Private cottage rentals

Top guest favorite
The inviting living space features a rustic wooden dining table surrounded by four chairs. A comfortable sofa adorned with decorative pillows sits across from a stone fireplace, while large glass doors open to a private patio with garden views.
Cottage in Kirkbymoorside

Farndale Cottage North York Moors National Park

4.98 out of 5 average rating, 163 reviews
Top guest favorite
A charming cottage with a red-tiled roof is situated alongside a pebbled pathway. The inviting exterior features a mix of brick and stone finishes, with white-framed windows. Adjacent, a historic stone church with a tower is visible, creating a serene backdrop amidst a well-maintained garden.
Cottage in Carlton-in-Cleveland

Old Fire Station Cottage | EV Charger | Opt 2nd BR

4.97 out of 5 average rating, 184 reviews
Top guest favorite
The kitchen features modern fitted units with a wooden countertop and a dining table surrounded by wooden chairs. A variety of appliances, including a microwave and kettle, are visible. The traditional cast iron cooking range adds character to the space, contrasting with the contemporary design.
Cottage in Loftus

No pets Coastguard Cottage in heart of Staithes

4.88 out of 5 average rating, 184 reviews
Guest favorite
A scenic view of a rural road winding through a lush valley, framed by greenery and flowering bushes. Traditional cottages with chimneys are visible, nestled against rolling hills under a partly cloudy sky, creating a peaceful countryside atmosphere.
Cottage in Glaisdale

Hollin Hall GT FryupDale, North York Moors Whitby.

4.87 out of 5 average rating, 424 reviews
Top guest favorite
A charming stone cottage is set against a backdrop of greenery, featuring arched windows and a slate roof. The garden includes well-maintained flower beds and a low stone wall, contributing to the serene cottage environment under a partly cloudy sky.
Cottage in Whitby

The Granary, at Millinder House for up to 4

4.92 out of 5 average rating, 219 reviews
Top guest favorite
A stone fireplace serves as a focal point in the living area, featuring an ornate mantel and a cozy log burner. A flat-screen television is mounted above the fireplace. Natural light filters from a nearby lamp, illuminating a comfortable sofa adorned with soft cushions.
Cottage in Hinderwell

Saltwater-Beautiful, cosy old fisherman's cottage

4.99 out of 5 average rating, 182 reviews
Top guest favorite
A brick cottage with two stories showcases a well-maintained front garden. Two entrances are framed by small potted plants, with evenly spaced windows allowing natural light to enter. The surrounding greenery adds to the rural charm of the property.
Cottage in Northallerton

Church Cottage, West Rounton, North Yorkshire

4.95 out of 5 average rating, 262 reviews
Top guest favorite
Two white wooden chairs are positioned near a large window, offering views of the sea and harbor. A decorative seagull figurine stands on the sill beside two glasses, with a small vessel and a sign visible on the wall.
Cottage in Loftus

Views to die for at Garr End Cottage Staithes.

4.94 out of 5 average rating, 305 reviews

Destinations to explore