Featured Group Cottages
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Quayside
North of England, Yorkshire
Quayside is a spacious five-bedroom family home in Sandsend, North Yorkshire. This coastal property sits just 100 metres from the beach and sleeps up to 10 guests. Groups will appreciate the...
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Sterling House
North of England, Yorkshire
Sterling House is a spacious semi-detached Victorian villa occupying the top two floors of a period property in Robin Hood's Bay, North Yorkshire. This impressive accommodation sleeps up to 8...
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Burtree House
North of England, Yorkshire
Burtree House is a spacious five-bedroom holiday home in Whitby, North Yorkshire. This property sleeps up to 10 guests and sits less than half a mile from the beach. Two well-behaved dogs are...
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Woodhead Farm Cottage
North of England, Yorkshire
Woodhead Farm Cottage is a substantial stone property sleeping 10 guests in the heart of Great Fryup Dale, North York Moors National Park. This five-bedroom retreat offers a full-size pool table...
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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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The Haggs
North of England, Yorkshire
The Haggs is a spacious four-bedroom holiday house in Sandsend, North Yorkshire. This bright property sleeps seven guests and sits just half a mile from the beach. Groups benefit from private...
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Bartley House Whitby
North of England, Yorkshire
Bartley House Whitby is a three-storey townhouse sleeping eight guests in North Yorkshire. This property sits moments from Whitby Harbour and offers excellent accommodation for families or groups...
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2 The Close
North of England, Yorkshire
2 The Close is a contemporary semi-detached bungalow perched on the cliff-front in Robin Hood's Bay, North Yorkshire. This four-bedroom property sleeps eight guests and offers spectacular sea...
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Sanders House
North of England, Yorkshire
Sanders House is a historical four-bedroom cottage in Whitby, North Yorkshire. This property sleeps eight guests across four floors. The central location puts shops, restaurants and pubs within a...
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Haven House
North of England, Yorkshire
Haven House is a modern four-bedroom terrace townhouse in Whitby. It sleeps eight people across three floors. This North Yorkshire property sits in a quiet location just ten minutes' walk from the...
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Explorers Retreat
North of England, Yorkshire
Explorers Retreat is a semi-detached cottage sleeping eight guests in the heart of Whitby, Yorkshire. This property works brilliantly for larger groups wanting a seaside base. You get four...
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Old Theatre
North of England, Yorkshire
Old Theatre is a Georgian townhouse sleeping eight guests in Whitby, North Yorkshire. This four-storey property sits between Pannett Park and the historic harbour. Groups get two separate living...
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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21 Eskdaleside
North of England, Yorkshire
21 Eskdaleside is a welcoming three-storey house in the North York Moors, specifically arranged for shared holidays. It sleeps six guests across four bedrooms, making it a solid pick for a group...
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30 Prospect Hill
North of England, Yorkshire
30 Prospect Hill is a large Victorian townhouse in Whitby, North Yorkshire one of the most well-known coastal towns on the Yorkshire coast. This is a solid choice for groups wanting a proper...
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Sunnyvale House
North of England, Yorkshire
Sunnyvale House is a seven-bedroom property spread across four floors in Whitby, North Yorkshire. It sleeps a large group comfortably and sits close to the beach, the town centre and the North...
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Esk House
North of England, Yorkshire
Esk House is a stunning Victorian four-storey town house built in 1855 in the heart of Whitby, North Yorkshire. This impressive property sleeps eight guests across four bedrooms and offers onsite...
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Ellingham House
North of England, Yorkshire
Ellingham House is an Edwardian four-bedroom terraced townhouse in Whitby, North Yorkshire. This property sleeps eight guests and sits less than half a mile from West Pier. Three king-size...
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Endeavour House
North of England, Vale of York
Endeavour House is a spacious York property perfect for larger groups wanting to explore this historic city. Located in North Yorkshire, this substantial townhouse offers excellent group...
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The Railway Retreat
North of England, Yorkshire
The Railway Retreat is a spacious four-bedroom townhouse in Whitby, North Yorkshire. This property works brilliantly for larger groups wanting to explore the Yorkshire coast. Off-road parking for...
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Seasiders Retreat
North of England, Yorkshire
Seasiders Retreat is a five-star property sleeping eight guests in Whitby, Yorkshire. This three-storey property works brilliantly for larger groups with four generously sized bedrooms, a covered...
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The Stables at Airy Hill Manor
North of England, Yorkshire
The Stables at Airy Hill Manor is a five-star property sleeping eight guests in Whitby, North Yorkshire. This renovated property sits less than half a mile from the historic harbour. Groups get...
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Craggill House
North of England, Yorkshire
Craggill House is a stylish four-bedroom stone retreat sleeping eight in the Esk Valley, North Yorkshire. This property sits on the edge of the North York Moors National Park, perfect for groups...
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.