The Finest Holiday Homes

45 properties found that match your search

So Grand - Large Holiday Cottages

Looking for a larger Southwold cottage for a break with friends and family? All of our Southwold cottages below sleep eight people or more and are perfect for enjoying a holiday in Southwold with those closest.

If you’ve gathered a large group together and want to visit this fabulous seaside town, we think we’ve got the best selection of large cottages! Property types include grand Georgian houses, seaside townhouses with most being in prime position in Southwold itself. All our large Southwold cottages offer plenty of space for your holiday.

There is so much to see and do with your friends and family in Southwold. For those who fancy a thrilling day out why not book the Coastal Voyager?  Or for those who fancy a more relaxing approach to their holiday the beach is the perfect place to soak up the sun and breathe in the seaside air.

If you want to bring a four-legged friend with you some of our large Southwold cottages are dog-friendly too! Some of our great big Suffolk cottages are dog-friendly too - so you won’t have to leave anyone behind! 

So whether you want to book a Christmas holiday with the family or a weekend break with friends, Southwold is the place for you and our large Southwold cottages are the perfect choice!

James Cottage

Southwold - Suffolk

For rooms with a view, scene-stealing features and space that ten can share comfortably, look no further than this lovingly-updated, centrally-located cottage.

  • Sleeps 10
  • 5 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£830 - £2150 per week *

HJAMES View property

  • Sleeps 10
  • Bed linen included
  • 5 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • 4 Single beds
  • 2 Double beds
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
Awarded 4 Star Gold with Original Cottages

Special Offer Southwold House

Southwold - Southwold

Style, substance and a sought-after location make this super-sized house the perfect holiday haven for a large group get-together.

  • Sleeps 10
  • 6 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£1130 - £3295 per week *

AASOUT View property

  • Sleeps 10
  • Bed linen included
  • 6 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • 4 Single beds
  • 1 Double bed
  • 2 King size/super king size beds
  • WiFi
  • 4.5 stars
Awarded 5 Stars with Original Cottages

New Property Hill House

Southwold - Southwold

Exceptional living spaces, elegant styling and a prime location make this prestigious property perfect for a big group gathering – prepare to be impressed, and then some!

  • Sleeps 11
  • 5 bedrooms
  • 5 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£2285 - £4540 per week *

HILS View property

  • Sleeps 11
  • Bed linen included
  • 5 bedrooms
  • 5 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 3 Single beds
  • 4 King size/super king size beds
  • WiFi
  • Equipped with a highchair
  • 5 stars
Awarded 5 Stars with Original Cottages

Special Offer The Creek House

Reydon - Suffolk

There’s luxury at every level in this unique holiday home – it’s tailor-made for group getaways, and from both inside and out the views over the surrounding countryside are spectacular!

  • Sleeps 12
  • 5 bedrooms
  • 4 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£1995 - £3290 per week *

CREH View property

  • Sleeps 12
  • Bed linen included
  • 5 bedrooms
  • 4 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 2 Single beds
  • 3 King size/super king size beds
  • 2 Single bunk beds
  • 2 Single zip & link beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 5 stars

Our Price Guarantee

If you find a So Southwold holiday cottage cheaper anywhere else online, we'll match the price.
Terms & Conditions apply. Find out more

Awarded 4 Star Gold with Original Cottages

3 Centre Cliff

Southwold - Southwold

‘Des res’ doesn’t even begin to describe this gorgeously grand holiday home… ideal for a large group getaway, its location will make you the envy of all!

  • Sleeps 12
  • 5 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£1530 - £5075 per week *

AA3CEN View property

  • Sleeps 12
  • Bed linen included
  • 5 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • 3 Single beds
  • 3 King size/super king size beds
  • 3 Single bunk beds
  • WiFi
  • 4.5 stars
Awarded 5 Star Gold with Original Cottages

Exterior - View 1 South Green House

Southwold - Suffolk

South Green House is a grand self-catering property located in one of Southwold's best locations - South Green.

  • Sleeps 12
  • 6 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£2630 - £4840 per week *

SGHS View property

  • Sleeps 12
  • Bed linen included
  • 6 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • 2 Single beds
  • 2 Double beds
  • 2 King size/super king size beds
  • 2 Single bunk beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 5.5 stars
Awarded 4 Star Gold with Original Cottages

1.jpg Samovar.

Southwold - Southwold

The epitome of composure and elegance, this double-fronted Edwardian house lends itself to large party or multi-generational group getaways.

  • Sleeps 12
  • 6 bedrooms
  • 3 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£1440 - £3170 per week *

AASAMO View property

  • Sleeps 12
  • Bed linen included
  • 6 bedrooms
  • 3 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • 4 Single beds
  • 2 King size/super king size beds
  • 2 Single bunk beds
  • WiFi
  • 4.5 stars
This Property is Awaiting Grading

Special Offer St Edmunds House

Southwold - Southwold

Evidence indeed that big is beautiful, this Edwardian family home simply exudes elegance – it’s the perfect excuse to get all the gang together and plan your next group getaway!

  • Sleeps 12
  • 6 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£1570 - £3170 per week *

STED View property

  • Sleeps 12
  • Bed linen included
  • 6 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • 2 Single beds
  • 2 King size/super king size beds
  • 2 Single bunk beds
  • 4 Single zip & link beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair

Our Price Guarantee

If you find a So Southwold holiday cottage cheaper anywhere else online, we'll match the price.
Terms & Conditions apply. Find out more

Awarded 5 Star Gold with Original Cottages

Special Offer Kitchen - View 2 Chelsea Villa

Southwold - Suffolk

Live like an A-lister in this luxurious seafront residence – with immaculately detailed interiors and a prime location, it exudes just as much class as the Royal Borough after which it's named...

  • Sleeps 14
  • 6 bedrooms
  • 5 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£2599 - £5295 per week *

CVIL View property

  • Sleeps 14
  • Bed linen included
  • 6 bedrooms
  • 5 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • 1 King size/super king size bed
  • 4 Single bunk beds
  • 8 Single zip & link beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 5.5 stars

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