The Finest Holiday Homes

86 properties found that match your search

So Romantic - Romantic Retreats

Escape to this fantastic coastal resort for a romantic holiday for two. Southwold is a beautiful town and ideal for a couples' break. All of our romantic cottages featured below sleep two guests only and are perfect for you and your loved one.

Our selection of self-catering cottages for two are perfect for couples wanting to spend a romantic holiday or short break together. From moonlit walks along the beach to a fun-filled brewery tour hosted by Adnams, you’ll have the perfect couples’ retreat to come home to. Our Southwold self-catering cottages also offer the flexibility to enjoy cosy candlelit dinners at home or a romantic meal out in Southwold’s vast selection of pubs and restaurants. The choice is yours.

We look forward to welcoming you to this truly special seaside resort and if you need further assistance in booking a romantic retreat for two, don’t hesitate to call the team!

Awarded 4 Stars with Original Cottages

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.

  • Sleeps 6
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£500 - £1125 per week *

SPI View property

  • 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

New Property Sandcastle Cottage

Southwold - Southwold

Situated in the heart of the popular coastal town of Southwold close to the beach Sandcastle Cottage is the ideal retreat for any family or group of friends on your next self catering stay in Suffolk.

  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£700 - £1635 per week *

SDCO View property

  • Sleeps 6
  • Bed linen included
  • 3 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 King size/super king size bed
  • 2 Single zip & link beds
  • WiFi
  • Open fire/woodburner
  • Travel cot available
  • Equipped with a highchair
  • 4 stars
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.

  • Sleeps 6
  • 3 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£615 - £1610 per week *

QST View property

  • 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

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.

  • Sleeps 6
  • 3 bedrooms
  • 1 bathroom
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • WiFi
£620 - £1660 per week *

SL130 View property

  • 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

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

Vicary's House

Southwold - Suffolk

Vicary's is a cosy holiday cottage ideal for those looking to be based close by to all Southwold's charms such as the shops, pubs, restaurants and beach.

  • Sleeps 7
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£675 - £1725 per week *

VIC View property

  • Sleeps 7
  • Bed linen included
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
  • 3 Single beds
  • 2 King size/super king size 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.

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

LON View property

  • 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
Awarded 4 Stars with Original Cottages

Gather round this nautical inspired dining table with benches for seating. Montague House

Southwold - Suffolk

Montague House is large property located on Southwold High Street. It is also known as the house where George Orwell lived for a time. The property has been furnished to a very high standard.

  • Sleeps 7
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£855 - £1695 per week *

MTH View property

  • Sleeps 7
  • Bed linen included
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
  • 3 Single beds
  • 2 Double beds
  • WiFi
  • Cot available
  • Equipped with a highchair
  • 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.

  • Sleeps 8
  • 3 bedrooms
  • 3 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • No private parking
  • WiFi
£805 - £1545 per week *

WHE View property

  • 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

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

Special Offer 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.

  • Sleeps 8
  • 3 bedrooms
  • 3 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • WiFi
£1595 - £3195 per week *

SOG View property

  • Sleeps 8
  • Bed linen included
  • 3 bedrooms
  • 3 bathrooms
  • No pets allowed
  • No garden/courtyard
  • No private parking
  • 1 Double bed
  • 1 King size/super king size bed
  • 4 Single bunk beds
  • WiFi
  • 4 stars
Awarded 5 Stars with Original Cottages

Castle Keep

Southwold - Suffolk

Escape to Castle Keep and live like a monarch – this unique and impressive holiday home boasts commanding views and a magnificent amount of space both inside and out.

  • Sleeps 8
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£1710 - £3200 per week *

CAST View property

  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
  • 2 Double beds
  • 2 Single bunk beds
  • 1 Single zip & link bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 5 stars
Awarded 5 Stars with Original Cottages

Small Group Discount Exterior - View 2 The Lollypop House

Southwold - Suffolk

The Lollypop House is the ideal luxury retreat by the seaside. It offers first class accommodation with benefits from a large garden and parking.

  • Sleeps 8
  • 4 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£1475 - £2930 per week *

LOL View property

  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
  • 4 Single beds
  • 2 King size/super king size beds
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 5 stars
Awarded 4 Star Gold with Original Cottages

Open Plan Room - View 1 Beachy Keen

Southwold - Suffolk

An ultra-trendy holiday cottage with its pastel colour palette and beach-themed tones throughout - self-catering holidays at Beachy Keen couldn't be any more stylish…

  • Sleeps 8
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • WiFi
£1005 - £1955 per week *

FFC View property

  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 4 Single beds
  • 2 Double beds
  • WiFi
  • Open fire/woodburner
  • 4.5 stars

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