Featured Group Cottages
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Bill's House
North of England, Yorkshire
Airy Hill Farm Cottage is a stone-built semi-detached barn conversion on the edge of Whitby in North Yorkshire. This property sleeps 11 guests across six bedrooms with six bathrooms, making it...
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Harbour Sunset
North of England, Yorkshire
Harbour Sunset is a three-storey property sleeping eight guests in Whitby, North Yorkshire. This stylish accommodation overlooks the working harbour and provides an excellent base for families and...
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The Pirate's Palace
England, Yorkshire
The Pirate's Palace is a luxurious, quirky period property dating from the 1860s set in the heart of Whitby, North Yorkshire. Spread across three floors of a beautifully renovated townhouse, this...
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Harbour House
North of England, Yorkshire
Harbour House is a Georgian townhouse spread over three floors in the heart of Whitby, North Yorkshire. This property sleeps eight guests and sits just minutes from the harbour and beach. The...
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Stewart House
North of England, Yorkshire
Stewart House is a Grade II listed Georgian townhouse built in 1760 in Whitby, North Yorkshire. This magnificent seven-bedroom property sleeps 12 guests across three floors, making it perfect for...
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Vega
North of England, Yorkshire
Vega is a stylish detached holiday home in Whitby, North Yorkshire that sleeps seven guests. This property works brilliantly for groups and families with four bedrooms, two bathrooms and generous...
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Arncliffe View Egton
North of England, Yorkshire
Arncliffe View Egton is a stone cottage sleeping eight guests in the North York Moors National Park village of Egton. This four-bedroom property sits just 50 metres from two country pubs serving...
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The Briary Danby
North of England, Yorkshire
The Briary Danby is a four-bedroom cottage in the village of Danby, North Yorkshire. This property sleeps six guests and sits within the North York Moors National Park. The open-plan lounge...
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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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Beacon House
North of England, Yorkshire
Beacon House is a semi-detached holiday home sleeping eight guests in Sneaton, North Yorkshire. This property works brilliantly for groups wanting space to spread out. The self-contained games...
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12 St Hilda's
North of England, Yorkshire
12 St Hilda's is a luxurious Georgian residence in Whitby, North Yorkshire. This five-bedroom property sleeps 13 guests and offers off-road parking for four cars. The house features a dedicated...
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Regatta House
North of England, Yorkshire
Regatta House is a stunning four-bedroom period property in Whitby, North Yorkshire. This spacious home sleeps eight guests across four beautifully appointed bedrooms. Perfect for larger groups,...
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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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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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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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...
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Woodman House
England, Yorkshire
Woodman House is a detached holiday home near Sleights in the North York Moors National Park, making it a solid pick for groups wanting space and countryside on the doorstep. Set in one of...
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Cobble Cottage
England, Yorkshire
Cobble Cottage is a traditional stone cottage in Goathland, North Yorkshire, sitting within the North York Moors National Park. This is a solid pick for groups wanting a proper countryside 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.