Winchester
A compact historic centre with a good spread of pubs, wine bars and restaurants
Local Guide
Hampshire works especially well for groups who want one house, enough space to stay together, and easy access to restaurants, activities, and day-trip options nearby. Browse live large group houses first, then add experiences like private chefs, spa treatments, or cocktail masterclasses once you've chosen the right base for your dates.
Hampshire runs from the New Forest in the west to the South Downs in the east, with a maritime coast between them at Portsmouth and Southampton. Winchester was England's ancient capital and still has one of the great cathedrals. For groups it offers forest, downland and coast within a small area, and it is close enough to London for a weekend without a long drive.
Roughly an hour from London Waterloo to Winchester; Southampton and Portsmouth are a little further
The M3 and A34 give quick access; 1.5–2 hours from London and under an hour from Bristol's direction via the A303
Rural services are limited across the Forest — a minibus is the practical option for a large group
Southampton Airport sits between Winchester and the city, with Heathrow around an hour away
Destination guide last reviewed August 2026.
Available Now
1 live listing — ready for your enquiry.
From £695 / night
2 nights ≈ £1,390 · ~£86 per person
No booking fees
A superb detached 7 bedroom Victorian house situated a minute from the Historic Portsmouth Harbou…
After dark
A compact historic centre with a good spread of pubs, wine bars and restaurants
The largest choice in the county, including bars around Oxford Street and the waterfront
Village pubs at Brockenhurst, Burley and Lyndhurst — the Forest's version of a night out
Venues, opening hours and door policies change — check ahead before planning your night around a specific spot.
Eat well
A Georgian harbour town with a Saturday market and cafes along the quay
Independent coffee houses and a well-regarded farmers' market near the cathedral
Village tearooms across the Forest, most used to walkers and larger parties
Restaurants and menus change — check ahead and book for larger groups.
Days out
Open forest and heath with free-roaming ponies, walking and cycling throughout
One of the largest cathedrals in Europe, with the city's medieval core around it
HMS Victory, the Mary Rose and the Spinnaker Tower on the harbour
Chalk downland walking along the eastern side of the county
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