The Finest Holiday Homes

76 properties found that match your search

Southwold Short Breaks

As Southwold locals, we’re undoubtedly biased when it comes to recommending the benefits of a short break in our beautiful, seaside town. However, there really is an endless list of a reasons why Southwold is the perfect destination for a mini break or a weekend away.

If food glorious food is on your mind, you’ll mind a mouth-watering choice of dishes at the unbeatable range of eateries around town. Whether you fancy a portion of the local catch (it’s so fresh it’s almost still swimming), a hearty plate of Dingley Dell Sausages & Mash or a gourmet A La Carte meal in one of the High Street hotels, there’s plenty of choice to whet your appetite

If you can’t bear to leave your four-legged friend at home, simply book one of our dog-friendly cottages which will have your pet wagging his tail all the way home from the beach!

During the off-peak season, you can start your short break on almost any day of the week, which offers greater flexibility for your coastal getaway. So don’t delay, book your short break getaway today! If you need further assistance don't hesitate to call our friendly So Southwold team on tel: 01502 543133.

Awarded 4 Stars with Original Cottages

Sitting Room - View 1 9 The Craighurst

Southwold - Suffolk

9 The Craighurst has been modernised and furnished beautifully. It is a first and second floor apartment with glorious sea views being opposite the seafront.

  • Saturday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • No garden/courtyard
  • No private parking
£620 - £1540 per week *

SL130 View property

  • Saturday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 Double bed
  • 1 King size/super king size bed
  • WiFi
  • 4 stars
Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

The Old Drapery

Southwold - Suffolk

Rich interior details and dramatic seafront views dominate in this high-quality apartment. The building may be historic, but all the holiday mod cons and must-haves are here. Arrive, unpack and unwind…

  • Saturday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
£605 - £1375 per week *

TOD View property

  • Saturday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 1 King size/super king size bed
  • 4 Single zip & link beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages

Special Offer Spindrift in Southwold is centrally located and is a beautiful property over four floors, ground, first, second and third. Spindrift

Southwold - Suffolk

This modern property is the ideal self-catering abode with all Southwold's charming shops within easy reach.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • Garden/courtyard
  • No private parking
£500 - £1040 per week *

SPI View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 Double bed
  • 2 Single zip & link beds
  • WiFi
  • Travel cot available
  • 4 stars
Awarded 4 Stars with Original Cottages

Kitchen - View 1 Shell House

Southwold - Suffolk

Shell House is set a couple of streets back from the shoreline, but this fabulous holiday home is full of seaside influence.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
£545 - £1415 per week *

STRD View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • 4 Single beds
  • 1 King size/super king size bed
  • WiFi
  • Open fire/woodburner
  • 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

Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

Special Offer Suffolk Cottage is a beautiful spacious property situated in Suffolk's premiere seaside town - Southwold. Suffolk Cottage

Southwold - Suffolk

Suffolk Cottage is a delightful cottage, beautifully and thoughtfully furnished, situated in the heart of Southwold.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
£730 - £1560 per week *

STH View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 2 Single beds
  • 2 King size/super king size beds
  • WiFi
  • Open fire/woodburner
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages

A plush seating area in front of the open fire will encourage warmth and a sense of luxury. 3 Queen Street

Southwold - Suffolk

3 Queen Street retains many character features including Georgian panelling in the sitting room. The property would be the perfect holiday for family gatherings beside the seaside.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
£615 - £1495 per week *

QST View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 Double bed
  • 1 King size/super king size bed
  • WiFi
  • Open fire/woodburner
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
Awarded 4 Stars with Original Cottages

Small Group Discount Living Room - View 1 Bada Bing

Southwold - Suffolk

The name sets off smiles... and there's so much to be happy about when you stay at this stylish holiday home.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • Garden/courtyard
  • Private parking
£595 - £1470 per week *

BAB View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 1 Double bed
  • 2 Single bunk beds
  • 2 Single zip & link beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

Special Offer Open Plan Room - View 1 Little Ducks

Southwold - Suffolk

Take off to this light, bright and oh-so-welcoming holiday cottage and feed your need for some laid-back living…. opulent yet supremely comfortable.

  • Saturday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • No private parking
£800 - £1415 per week *

TTHS View property

  • Saturday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 Double bed
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 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

Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

Kitchen/Dining Area - View 1 Rowan Villa

Southwold - Suffolk

Rowan Villa is a homely self-catering property situated within the heart of Southwold offering a mix of period and modern features.

  • Friday changeover day
  • Sleeps 6
  • 3 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
£775 - £1725 per week *

RVIL View property

  • Friday changeover day
  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • 2 Single beds
  • 1 Double bed
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages

Exterior - View 1 10B South Green

Southwold - Suffolk

10b South Green is a first and second floor apartment in the privileged location of Southwold, on South Green, the unbroken views of both the sea and over to Walberswick are second to none.

  • Friday changeover day
  • Sleeps 8
  • 3 bedrooms
  • 3 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
£1595 - £3070 per week *

SOG View property

  • Friday changeover day
  • Sleeps 8
  • Bed linen included
  • 3 bedrooms
  • 3 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • 2 Double beds
  • 4 Single bunk beds
  • WiFi
  • 4 stars
Awarded 4 Stars with Original Cottages

Exterior - View 2 Wherry Cottage

Southwold - Suffolk

Wherry Cottage is a comfortably furnished holiday cottage perfect for a family gathering in Southwold.

  • Friday changeover day
  • Sleeps 8
  • 3 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
£805 - £1575 per week *

WHE View property

  • Friday changeover day
  • Sleeps 8
  • Bed linen included
  • 3 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • 4 Single beds
  • 2 Double beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
Awarded 4 Stars with Original Cottages

Small Group Discount Exterior- View 1 Long Summers House

Reydon - Suffolk

A newly built three storey property situated in Reydon, Long Summers House is a delightful holiday choice.

  • Saturday changeover day
  • Sleeps 7
  • 4 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
£535 - £1100 per week *

LON View property

  • Saturday changeover day
  • Sleeps 7
  • Bed linen included
  • 4 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • 3 Single beds
  • 2 King size/super king size beds
  • WiFi
  • 4 stars

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