Featured Group Cottages
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Dale View
North of England, Yorkshire
Dale View is a Grade 2 listed detached barn conversion sleeping 13 guests in Lealholm, nestled in the North York Moors National Park. This spacious property offers six bedrooms and four bathrooms,...
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Dirlea Cottage
North of England, Yorkshire
Dirlea Cottage is a four-bedroom property in Ainthorpe near Danby in the North York Moors. This rural retreat sleeps seven guests and works well for families or friends wanting to explore...
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Crossbutts Farmhouse
North of England, Yorkshire
Crossbutts Farmhouse sits on the outskirts of Whitby in North Yorkshire. This farmhouse sleeps 10 guests across four bedrooms. Two private hot tubs in the enclosed rear garden make this perfect...
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Harbour View Whitby
North of England, Yorkshire
Harbour View Whitby is a five-star apartment in the heart of Whitby, North Yorkshire. This luxury property sleeps 10 guests across five bedrooms. Each bedroom has its own en-suite bathroom, making...
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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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Aislaby Hall
North of England, Yorkshire
Aislaby Hall is a grand 18th-century property sleeping 10 guests in the village of Aislaby, near Whitby in North Yorkshire. This historic house works brilliantly for larger groups with five...
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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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Bosuns Cottage
North of England, Whitby
Bosuns Cottage is an award-winning four-bedroom property in Whitby, North Yorkshire. This spacious former smoke house sleeps eight guests and sits right on the eastern edge of town. Sea views...
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Harbour Hideaway
North of England, Yorkshire
Harbour Hideaway is a four-bedroom Victorian terrace house sleeping eight guests in Whitby, North Yorkshire. This spacious property sits just minutes from Whitby Harbour and offers off-road...
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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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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...
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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...
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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South Haven
North of England, Whitby
South Haven offers a peaceful countryside retreat in Lincolnshire, perfect for larger groups wanting to escape together. This spacious lodge provides plenty of room for everyone to spread out and...
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Captain’s House
North of England, Whitby
Captain's House is a modern town house located in Whitby on the Yorkshire Heritage Coast. This property sits just a short walk from the town centre, making it perfect for groups who want easy...
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Carmel
North of England, Whitby
Carmel is a well-appointed lodge in Lincolnshire that works brilliantly for larger groups wanting a countryside escape. This spacious property sits in peaceful surroundings and gives everyone room...
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Harbourside House
North of England, Whitby
Harbourside House is a modern end townhouse in Lincolnshire, perfect for groups of up to eight guests. This spacious three-storey property offers plenty of room for everyone to spread out and...
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Captains Cottage in Whitby
North of England, Whitby
Captains Cottage in Whitby offers spacious accommodation for larger groups in the heart of this historic North Yorkshire coastal town. This traditional holiday home sits within walking distance of...
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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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Heron Mews
North of England, Whitby
Heron Mews is a three-storey mews cottage in Whitby, North Yorkshire, sleeping up to 8 guests. This property works brilliantly for larger families or two families sharing. The master bedroom...
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Esk View at Captains Row
North of England, Whitby
Esk View at Captains Row is a Victorian sea captain's residence from 1859 in Whitby, North Yorkshire. This spacious property sleeps 12 guests and retains original features throughout. Groups will...
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Frankland House
North of England, Whitby
Frankland House is a six-bedroom Victorian townhouse sleeping 12 guests in Whitby, North Yorkshire. This restored 1868 ship officers' residence sits just half a mile from the beach and a...
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.