Featured Group Cottages
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Meadowfields
North of England, Yorkshire
Meadowfields is a contemporary detached property sleeping eight guests in the centre of Whitby, North Yorkshire. This four-bedroom home sits in a residential area just 0.4 miles from the town...
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Curlew Cottage Goathland
North of England, Yorkshire
Curlew Cottage Goathland is a spacious four-bedroom property in the North York Moors National Park. This home sleeps eight guests comfortably. It sits on the edge of Goathland village near Whitby....
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Calliope House
North of England, Yorkshire
Calliope House is a spacious four-bedroom holiday home in Whitby, North Yorkshire. This property sleeps eight guests across four well-appointed bedrooms. The location puts you right in the heart...
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Fern Lea
England, Yorkshire
Fern Lea is an imposing semi-detached Edwardian villa in Scarborough, North Yorkshire. This substantial property sleeps larger groups comfortably with spacious period features throughout. The...
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Normanby House
England, Yorkshire
Normanby House is a large self-catering property in the North York Moors National Park, North Yorkshire. Sitting close to the village of Ugthorpe near Whitby, this is a solid choice for groups...
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Baysdale Abbey at Baysdale Abbey
England, Yorkshire
Baysdale Abbey at Baysdale Abbey is a substantial historic country house set deep in Baysdale, a secluded valley in the North York Moors National Park, North Yorkshire. This is a large-group...
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Arden House
North of England, Yorkshire
Arden House is a four-bedroom cottage in Sleights, North Yorkshire. This property sleeps seven guests across three floors. The location puts you right on the edge of North York Moors National...
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Bosuns Cottage
England, Yorkshire
Bosuns Cottage is a spacious group holiday property located in Robin Hood's Bay, North Yorkshire one of the most striking coastal villages on the Yorkshire coast. This is a serious booking for...
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Hazeldene
North of England, Yorkshire
Hazeldene is a three-storey house in Sleights village, North Yorkshire. This property sleeps eight guests across four bedrooms with three bathrooms. Perfect for multi-generational family...
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Rokeby House
North of England, Yorkshire
Rokeby House is a Georgian holiday home in Robin Hood's Bay, North Yorkshire. This four-bedroom property sleeps eight people across two floors. Sea views from the first-floor sitting room and...
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Whitby View
North of England, Yorkshire
Whitby View is a three-storey holiday home sleeping eight guests in the heart of Whitby, North Yorkshire. This modern property sits on Windsor Terrace with off-road parking for two cars including...
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Trillo House
North of England, Yorkshire
Trillo House is a four-storey Georgian townhouse in Whitby, North Yorkshire. This property sleeps eight guests across four bedrooms. The hot tub in the enclosed courtyard offers a relaxing spot...
View CottagePlanning a Group Getaway in Whitby?
Planning a get-together on the North Yorkshire coast? Our collection of large holiday homes in Whitby provides the perfect base for groups of 8 to 20+ guests. From properties overlooking the historic harbour to coastal retreats in Robin Hood's Bay and Staithes, each features multiple bedrooms, spacious living areas and fully fitted kitchens. Many include private parking, gardens and modern amenities.
Whitby offers something for everyone. Walk the famous 199 steps to the Gothic abbey ruins. Explore the working harbour where Captain Cook learned his craft. Sample fresh fish and chips on the harbourside. Take boat trips to spot seals along the coastline. Visit shops selling locally crafted jet jewellery. The North York Moors Railway runs steam trains through moorland scenery to Pickering. Nearby Scarborough provides sandy beaches and traditional entertainment.
We're rated Excellent on Trustpilot and offer low deposits with flexible payments. Whether you're organising a family reunion or celebrating with friends, our pet-friendly properties with optional hot tubs ensure everyone travels together. Start planning your North Yorkshire break today.
Perfect for Every Group Size
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Helena
England, Yorkshire
Helena is a large group cottage in the heart of the North York Moors National Park, North Yorkshire. Sleeping up to 16 guests, this is a serious option for big family gatherings, milestone...
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Warren Farmhouse
England, Yorkshire
Warren Farmhouse is a large self-catering farmhouse property in North Yorkshire, sitting within the North York Moors National Park near Whitby. This is a serious group booking the farmhouse...
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Beacon House
England, Yorkshire
Beacon House is a large group holiday property in Whitby, North Yorkshire one of the most visited coastal towns on the Yorkshire coast. Described as a Captain's House, this is a substantial...
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Whitby Villa
England, Yorkshire
Whitby Villa is a Grade II listed Georgian townhouse in the heart of Whitby, North Yorkshire one of the most historically significant coastal towns in England. This is a serious group booking....
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Little Falcon
England, Yorkshire
Little Falcon is a three-storey townhouse right in the heart of Whitby, North Yorkshire one of the most visited coastal towns in England. For groups wanting a proper base in a real town rather...
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The Granary
England, Yorkshire
The Granary is a sandstone barn conversion sleeping 8 guests across 4 bedrooms, sitting on the edge of Whitby in North Yorkshire. Part of a row of four barn conversions beside the owner's...
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Larpool Mews
England, Yorkshire
Larpool Mews is a converted stable block in Whitby, North Yorkshire, originally part of the Georgian Larpool Hall estate. This historic stable conversion sleeps a large group and sits in a...
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Oak Hollow Pod
England, Yorkshire
Oak Hollow Pod is a striking five-bedroom townhouse spread across four floors in the heart of Whitby, North Yorkshire. This is a serious group booking think private parking for four cars, two...
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Oakwood
England, Yorkshire
Oakwood is a large group holiday property near Sleights in the North York Moors National Park, North Yorkshire. Sleeping a substantial number of guests across multiple lodges, this is a serious...
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Evergreen House
England, Yorkshire
Evergreen House is a well-presented, spacious holiday home in Runswick Bay, near Whitby on the North Yorkshire coast. It's a solid choice for groups and larger families who want a proper base...
View CottageSpecial Features
Pool Properties
Luxury cottages featuring private swimming pools for the ultimate relaxation experience.
View Pool CottagesPet Friendly
Bring your furry friends along! Properties with secure gardens and pet-friendly amenities.
View Pet-FriendlyEnclosed Gardens
Safe, private outdoor spaces perfect for families with children and pets to enjoy.
View CottagesPremium Hot Tubs
All our properties feature luxury hot tubs with stunning views of the Lake District.
View All CottagesHoliday Ideas
View allPet-Friendly Group Retreats
Spacious properties welcoming your four-legged family members
Bring your dogs along to our collection of pet-friendly cottages across Whitby and the North Yorkshire coast. Many properties feature enclosed gardens and direct access to coastal paths perfect for morning walks. Enjoy dog-friendly beaches at Sandsend and Robin Hood's Bay. Several local pubs welcome well-behaved dogs. Ground floor bedrooms and outdoor spaces make these homes ideal for groups travelling with pets.
Family Reunions
Multi-generational gathering spaces across Whitby
Our large family homes sleep up to 20 guests with multiple bathrooms and open-plan living areas. Ground floor bedrooms suit older relatives. Spacious dining tables seat everyone together. Kids love exploring Whitby's sandy beach and the famous 199 steps. Grandparents appreciate the historic abbey and Captain Cook museum. Large kitchens and utility rooms handle family-sized washing loads effortlessly.
Coastal Walking Groups
Perfect bases for Cleveland Way adventures
Base yourself near the Cleveland Way National Trail for spectacular coastal hiking. Properties with drying rooms and secure boot storage accommodate walking groups perfectly. The trail passes through Staithes and Robin Hood's Bay offering clifftop views. Plan circular routes through the North York Moors. Return to comfortable lounges and hot tubs after long days on the paths. Local pubs serve hearty meals.
Celebration Getaways
Milestone birthdays and special occasions
Celebrate significant birthdays and anniversaries in style at our luxury group properties. Many feature hot tubs and spacious gardens for outdoor gatherings. Large dining areas accommodate celebration meals. Book harbour-side restaurants for special dinners. Take group boat trips or steam train journeys. Properties with games rooms keep everyone entertained. Create memories together on the stunning North Yorkshire coast.