The Finest Holiday Homes

81 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 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

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

Exterior - View 1 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.

  • Saturday changeover day
  • Sleeps 7
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
£675 - £1600 per week *

VIC View property

  • Saturday changeover day
  • 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

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.

  • Friday changeover day
  • Sleeps 7
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • No private parking
£855 - £1645 per week *

MTH View property

  • Friday changeover day
  • 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 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.

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 4 bathrooms
  • 1 pet allowed
  • Garden/courtyard
  • Private parking
£1475 - £2715 per week *

LOL View property

  • Friday changeover day
  • 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 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.

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 3 bathrooms
  • 2 pets allowed
  • Garden/courtyard
  • Private parking
£1710 - £2970 per week *

CAST View property

  • Friday changeover day
  • 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

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

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…

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
£1005 - £1900 per week *

FFC View property

  • Friday changeover day
  • 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 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

Special Offer The open plan kitchen and dining area is light and airy with a view of the garden and provides access to the wet room. Northfield House

Southwold - Suffolk

Northfield House is a large property overlooking the Church green and offers beautifully appointed accommodation for a Southwold holiday.

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 4 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
£1270 - £2175 per week *

NHF View property

  • Friday changeover day
  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 4 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 4 Single beds
  • 2 King size/super king size beds
  • WiFi
  • Open fire/woodburner
  • 4 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages Original Cottages Family Gold Award Symbol

Small Group Discount The eight of you can gather at the glass dining table for a fabulous meal. Salisbury House

Southwold - Suffolk

Salisbury House is a modernised property with comtemporary furnishings throughout. It is situated within the heart of Southwold with the beach just a short walk away.

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • No garden/courtyard
  • No private parking
£975 - £1825 per week *

SAL View property

  • Friday changeover day
  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 2 bathrooms
  • 1 pet allowed
  • No garden/courtyard
  • No private parking
  • 2 Single beds
  • 1 Double bed
  • 2 King size/super king size beds
  • WiFi
  • 4 stars
  • VisitEngland Gold Award
Awarded 4 Stars with Original Cottages

Enjoy a few alfresco meals in this pretty garden with bright flowers, patio area, table and chairs and sun parasol. Beech House

Southwold - Suffolk

Beech House is a delightful property situated along Pier Avenue, a sought-after location for a Southwold holiday.

  • Friday changeover day
  • Sleeps 8
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
£995 - £1730 per week *

BHO View property

  • Friday changeover day
  • Sleeps 8
  • Bed linen included
  • 4 bedrooms
  • 2 bathrooms
  • No pets allowed
  • Garden/courtyard
  • Private parking
  • 6 Single beds
  • 1 King size/super king size bed
  • WiFi
  • Travel cot available
  • Equipped with a highchair
  • 4 stars

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