Featured Group Cottages
View all
Stone-Built Cottage for 8 in Sleights
North of England, Yorkshire
This 4-bedroom group cottage is a stone-built property in the North Yorkshire village of Sleights. This four-bedroom cottage sleeps eight guests and welcomes two dogs. The property sits just 100...
View Cottage
Captains Cottage
England, Yorkshire
Captains Cottage is a traditional cottage in Whitby, one of North Yorkshire's most popular coastal towns on the Yorkshire Coast. This is a solid choice for a group looking for a characterful base...
View Cottage
House for 8 in Whitby
North of England, Yorkshire
This 4-bedroom group house is a property sleeping eight guests in Whitby, Yorkshire. This three-storey property works brilliantly for larger groups with four generously sized bedrooms, a covered...
View Cottage
Cottage for 6 in Sleights
North of England, Yorkshire
This 4-bedroom group cottage is in Sleights, North Yorkshire. This property sleeps six people and works well for families or small groups. The cottage has original ceiling beams and a wood burner...
View Cottage
Bosuns Cottage
England, Yorkshire
Bosuns Cottage is a spacious group holiday property located in Whitby, North Yorkshire - one of the most striking coastal towns on the Yorkshire coast. This is a serious booking for larger groups...
View Cottage
Victoria Square
England, Yorkshire
Victoria Square is a Grade II listed townhouse in the heart of Whitby, North Yorkshire - a serious find for groups wanting a proper base in one of England's most visited coastal towns. This is a...
View Cottage
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...
View Cottage
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...
View Cottage
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...
View Cottage
Period House for 7 in Whitby
North of England, Yorkshire
This 4-bedroom group house is a 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...
View Cottage
Substantial Stone Cottage for 10 in Fryup
North of England, Yorkshire
This 5-bedroom group 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...
View Cottage
Georgian House for 8 near Newholm
North of England, Yorkshire
This 4-bedroom group house 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...
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
Recently Added
View all
Helena
England, Yorkshire
Helena is a large group cottage in the heart of the North York Moors National Park, North Yorkshire. Sleeping up to 12 guests, this is a serious option for big family gatherings, milestone...
View Cottage
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...
View Cottage
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...
View Cottage
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....
View Cottage
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...
View Cottage
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...
View Cottage
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...
View Cottage
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...
View Cottage
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...
View Cottage
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 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.