The Finest Holiday Homes

42 properties found that match your search

September Southwold Cottages

We like to refer to September as our secret summer season as it’s often lovely and warm and the perfect temperature for ambling along the beach. The sea has had a chance to warm up throughout August, so if you fancy a dip, remember to bring your bathers. This time of year is also perfect for discovering Southwold’s myriad of walking tracks. From gentle strolls to longer rambles along the coast, the stunning views will simply take your breath away. And don’t miss the chance to stroll along Southwold Pier – a pastime that has brought pleasure to countless visitors over the years. So for a relaxing break filled with as much or as little as you please, a holiday during our secret summer season could be just what you’re looking for. And the best thing about this time of year is that we have a wonderful selection of self-catering holiday cottages to choose from!

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Far View Two

Southwold - Suffolk

See a different side of Southwold from this lovely abode - with far-reaching views across the Common, it's ideal for two, tastefully presented and perfectly-positioned for unforgettable sunsets.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Sorry, no Private parking
£400 - £815 per week *

FV2 View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
  • VisitEngland Gold Award
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Bedroom - View 1 Southwold Surf

Southwold - Suffolk

The perfect self-catering abode for couples on a romantic getaway to this seaside destination.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£465 - £755 per week *

SUR View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • WiFi
  • 4 stars
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Luxurious sitting room with bay window and a great space for relaxation. Cliffside

Southwold - Suffolk

Cliffside is a lovely apartment situated in Southwold. It has modern, cosy accommodation for two people and there is also a parking space which is much sought after in this seaside town.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Private parking
£525 - £865 per week *

CLS View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Private parking
  • 1 Double bed
  • WiFi
  • 4 stars
  • VisitEngland Gold Award
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Open Plan Room - View 1 72A High Street

Southwold - Suffolk

Cosy and contemporary apartment in the heart of Southwold, 72A High Street is a fabulous base for a seaside break.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£425 - £775 per week *

HIST View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • WiFi
  • 4 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

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Bedroom - View 1 The Mews

Southwold - Suffolk

No classroom was ever this cool! A stylish apartment on the first floor of a former prep school, The Mews gets full marks as a holiday hideaway for two.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£485 - £735 per week *

MEWS View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • WiFi
  • 4 stars
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Far View One

Southwold - Suffolk

With stunning views across the Common, this traditionally-styled apartment is aptly named. It's the ideal choice for a couple's retreat – tucked away yet with easy access to town, beach and harbour.

  • Friday changeover day
  • Sleeps 2
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Private parking
£440 - £855 per week *

FV1 View property

  • Friday changeover day
  • Sleeps 2
  • Bed linen included
  • 1 bedroom
  • 1 bathroom
  • Sorry, no pets allowed
  • Garden/courtyard
  • Private parking
  • 1 Double bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • All on one level
  • 4 stars
  • VisitEngland Gold Award
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Living Room - View 2 3 Eversley Court

Southwold - Suffolk

Courting your attention is this modern mews house, part of a clever conversion of the former Eversley School.

  • Saturday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Sorry, no Private parking
£510 - £930 per week *

SL135 View property

  • Saturday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Sorry, no Private parking
  • 2 Single beds
  • 1 King size/super king size bed
  • WiFi
  • 4 stars
  • VisitEngland Gold Award
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Bedroom - View 1Sitting Room/Dining Area - View 1Kitchen - View 1 Black Cottage

Southwold - Suffolk

Black Cottage is a recently renovated self-catering cottage with easy access to Southwold High Street.

  • Friday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 1 bathroom
  • 1 pet allowed
  • Garden/courtyard
  • Sorry, no Private parking
£570 - £995 per week *

BLA View property

  • Friday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 1 bathroom
  • 1 pet allowed
  • Garden/courtyard
  • Sorry, no Private parking
  • 2 Single beds
  • 1 Double bed
  • WiFi
  • Open fire/woodburner
  • 4 stars
  • VisitEngland Gold Award

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

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Living Area - View 1 Sandy Castle

Southwold - Suffolk

The winner of the Home Award, Sandy Castle is a modern property tucked away in a quiet location within central Southwold.

  • Friday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 2 bathrooms
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£525 - £1005 per week *

SAN View property

  • Friday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 2 bathrooms
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
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Living Room - View 4 10 The Craighurst

Southwold - Suffolk

This lavishly-presented apartment enjoys an enviable position on Southwold's upper promenade and is the ultimate in opulent living.

  • Saturday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£615 - £1180 per week *

CR10 View property

  • Saturday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 1 bathroom
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 King size/super king size bed
  • 2 Single bunk beds
  • WiFi
  • Equipped with a highchair
  • All on one level
  • 4 stars
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Open Plan Sitting, Dining & Kitchen Area - View 1 The Lighthouse

Southwold - Suffolk

This pristine four-person apartment is part of a clever conversion just a short stroll from the seafront. Two pets are welcome too, so the whole family can share the holiday fun!

  • Friday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 2 bathrooms
  • 2 pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
£600 - £995 per week *

LTH View property

  • Friday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 2 bathrooms
  • 2 pets allowed
  • Sorry, no Garden/courtyard
  • Sorry, no Private parking
  • 1 Double bed
  • 2 Single bunk beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
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Master Bedroom High View

Southwold - Suffolk

This Edwardian second floor apartment for up to four guests offers a mix of period charm and modern touches and commanding views of Southwold from nearly every angle.

  • Saturday changeover day
  • Sleeps 4
  • 2 bedrooms
  • 2 bathrooms
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Private parking
£585 - £970 per week *

HVW View property

  • Saturday changeover day
  • Sleeps 4
  • Bed linen included
  • 2 bedrooms
  • 2 bathrooms
  • Sorry, no pets allowed
  • Sorry, no Garden/courtyard
  • Private parking
  • 2 Single beds
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars

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