May Half Term Holidays

The May Half Term break is the last opportunity to get away before the school’s finish for the six weeks of summer. With the combination of Spring and early summer, we’re usually quite lucky with the weather, and there’s always plenty of things to do. The longer days means more time to get out and explore Southwold and the surrounding areas.

All our holiday cottages below are available for a 7-night break during the May Half Term week. You can use the handy search filter tool below to refine your holiday search or alternatively give our friendly team a call on 01502 723292.

25 matching properties

Southwold1 Cumberland Close
Property Ref: 565444
This cosy Southwold apartment is just moments from Southwold's bustling High Street and glorious sandy beach, offering guests the very best the t...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £575 - £1,170 per week
Southwold10a East Cliff
Property Ref: 565396
Views, glorious views! 10a East Cliff gives guests the most impressive views of Southwold's most iconic areas.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £715 - £1,385 per week
Southwold1a Park Lane
Property Ref: 565412
Quirky Southwold cottage just moments from the picturesque South Green.
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 3
  • No Dogs
Price: £670 - £1,415 per week
Southwold26 Pier Avenue
Property Ref: 565401
26 Pier Avenue is a fantastic cottage for a family holiday with everything you could need for self-catering plus it has private parking!
  • Sleeps 8
  • Bedrooms 4
  • Bathrooms 2
  • No Dogs
Price: £940 - £2,250 per week
Southwold3 Pier Court
Property Ref: 565462
Modern holiday apartment with wonderful views towards Southwold Pier and the sea.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • Dogs 1
Price: £615 - £1,210 per week
Reydon, Southwold4 Church Cottages
Property Ref: 630591
Brimming with charm and character, this rural cottage between Southwold and Wangford enjoys scenic views and a cosy, homely interior.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • Dogs 1
Price: £610 - £1,095 per week
NEW
WalberswickBuntings
Property Ref: 637375
This delightful two-bedroom holiday home in the heart of Walberswick offers, style, space, convenience and character and is ideal for two couples or a...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £800 - £1,675 per week
SouthwoldCautley Cottage
Property Ref: 565424
If you’re looking for a lovely cosy and comfortable holiday cottage in the heart of Southwold with private parking then Cautley Cottage is for y...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £615 - £1,250 per week
SouthwoldCoastguards
Property Ref: 565411
A warm and welcoming refurbished Southwold cottage benefiting from many original features.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £625 - £1,265 per week
BecclesGarden Wing, Redisham Hall
Property Ref: 585315
If you feel like escaping to the country for a while, this is the holiday accommodation for you!
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £500 - £1,110 per week
SouthwoldHappy Days
Property Ref: 576188
Happy Days is a popular holiday choice with families looking to explore Southwold in more detail, plus you can bring your four-legged friend on holida...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • Dogs 1
Price: £655 - £1,380 per week
NEW
WalberswickHedges
Property Ref: 639854
A beautiful home-from-home bungalow tucked away on a peaceful lane in Walberswick.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £850 - £1,675 per week
SouthwoldHolly House
Property Ref: 615088
This traditional and spacious 1930’s holiday home boasts a central location and distant sea views plus private parking for two cars.
  • Sleeps 7
  • Bedrooms 4
  • Bathrooms 3
  • Dogs 1
Price: £815 - £2,280 per week
NEW
SouthwoldLighthouse Loft
Property Ref: 638585
A cool and contemporary apartment with Southwold’s beach and an Adnams pub right on the doorstep!
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • Dogs 1
Price: £725 - £1,425 per week
SouthwoldNuage
Property Ref: 611198
Enjoy superb views of the Suffolk Coast and a central Southwold location in this heavenly loft apartment.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £685 - £1,175 per week
SouthwoldPetrel Cottage
Property Ref: 565445
Oh so cute and cosy! This charming Southwold cottage is a lovely place to explore Southwold in more detail.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £640 - £1,120 per week
SouthwoldPippins
Property Ref: 565378
If you enjoy the bustle of a High Street then why not book Pippins and stay in Southwold's High Street with its abundance of boutiques, coffee sh...
  • Sleeps 5
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £545 - £995 per week
SouthwoldSandy Castle
Property Ref: 622540
Quirky and stylish, this fabulous holiday bolt hole sits in a hidden nook, just of Southwold High Street.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 2
  • No Dogs
Price: £810 - £1,595 per week
NEW
SouthwoldSeaside Cottage
Property Ref: 629947
A bright and beautifully presented character cottage in the heart of Southwold
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £725 - £1,575 per week
WangfordSparrows
Property Ref: 565437
Sparrows offers guests the best of both worlds - a countryside location yet just a short drive to the popular seaside town of Southwold. Sparrows is a...
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 2
Price: £620 - £980 per week
SouthwoldSt Elmo
Property Ref: 565403
Spacious, homely and well-appointed, St Elmo offers ideal accommodation for fun-filled family holidays by the sea.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 1
  • Dogs 1
Price: £685 - £1,425 per week
SouthwoldStuckie Ben
Property Ref: 627952
A traditional terraced cottage just a short walk from Gun Hill, Southwold common and the Red Lion.
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 2
Price: £650 - £1,175 per week
SouthwoldThe Old Bakery
Property Ref: 626778
If you’re looking for spacious holiday accommodation for two in the heart of Southwold, then The Old Bakery could be just for you!
  • Sleeps 2
  • Bedrooms 1
  • Bathrooms 2
  • No Dogs
Price: £630 - £1,175 per week
SouthwoldThe Original Seaside House
Property Ref: 587852
A comfortable family holiday home on one of Southwold’s quiet streets just a few steps from the seafront.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • No Dogs
Price: £476 - £862 per week
SouthwoldWheelhouse
Property Ref: 594181
A comfortable and cosy holiday cottage in the heart of Southwold, with a nod to all things nautical!
  • Sleeps 3
  • Bedrooms 2
  • Bathrooms 1
  • Dogs 1
Price: £595 - £1,175 per week

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