Featured Group Cottages
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Mariners' Rest
North of England, Yorkshire
Mariners' Rest is a semi-detached cottage in Whitby, North Yorkshire. This three-storey property sleeps eight people across four bedrooms. Off-road parking for two cars makes arrival easy for...
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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,...
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The Station House
North of England, Yorkshire
The Station House is a Grade II listed Victorian conversion in Ruswarp village, just 1.5 miles from Whitby. This former railway station and stationmaster's house sleeps 11 guests across five...
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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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4 Normanby Terrace
North of England, Yorkshire
4 Normanby Terrace is a six-bedroom terraced house in Whitby, North Yorkshire. This property sleeps 11 guests across three floors. Groups love the private hot tub in the enclosed back garden. The...
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The Farmhouse
North of England, Yorkshire
The Farmhouse is a traditional Yorkshire property sleeping eight guests near Robin Hood's Bay in North Yorkshire. This spacious farmhouse sits in private south-facing gardens with sweeping views...
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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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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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Isla House
North of England, Yorkshire
Isla House is a striking three-storey Victorian holiday home in Whitby, North Yorkshire. Built around 1860, this property sleeps eight guests and works brilliantly for larger groups wanting...
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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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Atlanta
North of England, Yorkshire
Atlanta is a 200-year-old cottage sleeping eight guests in High Hawkser, North Yorkshire. This property sits within the North York Moors National Park and offers four bedrooms with exposed beams...
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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...
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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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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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...
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2 West Terrace
North of England, Yorkshire
2 West Terrace is a four-bedroom period townhouse sleeping seven guests in Whitby, North Yorkshire. This property sits on the cobbled streets of West Cliff, just 300 metres from the beach and town...
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Mariner's Watch
North of England, Yorkshire
Mariner's Watch is a spectacular five-bedroom property in Whitby, North Yorkshire. This three-storey house sleeps 10 guests and offers 360-degree panoramic views across the bay, beach and historic...
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Beachcrest
North of England, Yorkshire
Beachcrest is a spacious five-bedroom family home in Whitby, North Yorkshire. This property sleeps 10 guests and sits right on the coast with direct views over Sandsend beach and the golf course....
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Keel House
North of England, Yorkshire
Keel House is a four-bedroom holiday home in Whitby, North Yorkshire. This spacious property sleeps seven guests across three floors. Off-road parking for two cars makes arrival simple. The...
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.