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.

32 matching properties

1 Cumberland Close Sitting Room View: The sitting room at 1 Cumberland Close in Southwold is light and spacious, comfortably furnished with a table for dining and feature fireplace

An external view of 1 Cumberland Close, a ground floor holiday apartment located in the heart of Southwold on the Suffolk Coast. The entrance is level and would suit those who are less able

1 Cumberland Close Dining Area View: Enjoy meal times at the round dining table in the sitting room at 1 Cumberland Close in Southwold, Suffolk

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: £686 - £1,158 per week

Lounge with dark green sofa and large smart TV at 10 East Street. Available from Durrants Holiday Cottages, Southwold

Kingsize bed with white linen and mustard cushions at 10 East Street. Available from Durrants Holiday Cottages, Southwold

Contemporary oak dining table and benches at 10 East Street. Available from Durrants Holiday Cottages, Southwold

Southwold10 East Street

Property Ref: 642091

A super-stylish, contemporary holiday home in the heart of Southwold with the High Street and beach on the doorstep.

Sleeps 8
Bedrooms 4
Bathrooms 2
Dogs 1

Price: £2,295 - £3,450 per week

NEW

Southwold12a Fieldstile Road

Property Ref: 652147

A truly homely ground floor apartment with a fabulous central location close to the High Street and beach.

Sleeps 2
Bedrooms 1
Bathrooms 1
Dogs 1

Price: £646 - £1,264 per week

17 St Edmunds Road, Southwold: Lounge with blue velvet soft and woodburner, available to let from Durrants Holiday Cottages, Suffolk

17 St Edmunds Road, Southwold: Spacious double bedrooms with comfy bed and checked throw, available to let from Durrants Holiday Cottages, Suffolk

7 St Edmunds Road, Southwold: Modern kitchen with cream shaker-style units,, available to let from Durrants Holiday Cottages, Suffolk

Southwold17 St Edmunds Road

Property Ref: 633795

Stylishly furnished, well-equipped and convenient for the town and beach, this comfy cottage is a real find!

Sleeps 4
Bedrooms 2
Bathrooms 1
Dogs 1

Price: £690 - £1,251 per week

3 Pier Court Open Plan Sitting Room and Dining Area

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: £651 - £1,196 per week

3 Trinity Street, Southwold. A holiday home above High Tide gift shop. Available from Durrants Holiday Cottages, Suffolk

Lounge at 3 Trinity Street with leather suite, fireplace and smart TV.

The dining area at 3 Trinity Street, Southwold with farmhouse style table and chairs. Available from Durrants Holiday Cottages, Suffolk

Southwold3 Trinity Street

Property Ref: 585165

Situated betwixt sea and High Street and a few short steps to the ‘Nelly’, this quirky and well-appointed holiday home is in the heart of ...

Sleeps 6
Bedrooms 3
Bathrooms 2
Dogs 1

Price: £578 - £1,552 per week

33 Victoria Street-Southwold-Durrants-Exterior

33 Victoria Street-Southwold-Durrants-sitting-room

Southwold33 Victoria Street

Property Ref: 565393

Beautifully presented Southwold cottage with coastal touches throughout, 33 Victoria Street is a modernised holiday cottage in the heart of the town.

Sleeps 4
Bedrooms 2
Bathrooms 2
Dogs 1

Price: £690 - £1,498 per week

4 Church Cottages Exterior: A charming red brick terraced Suffolk holiday cottage between Southwold and Wangford

4 Church Cottages Sitting Room: A warm and inviting room with comfortable sofas, holiday cottage near Southwold, Suffolk

4 Church Cottages Kitchen: The dining table is at the heart of this country style kitchen, holiday cottage near Southwold, Suffolk.

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: £640 - £1,072 per week

Sitting room at 5 Wymering Road, Southwold, let by Durrants Holiday Cottages

5 Wymering Road_Durrants_Southwold_ Front Exterior

5 Wymering Road_Durrants_Southwold_dining room

Southwold5 Wymering Road

Property Ref: 565384

A centrally located pet-friendly cottage, 5 Wymering Road is a cosy holiday home for families.

Sleeps 6
Bedrooms 3
Bathrooms 1
Dogs 1

Price: £805 - £1,402 per week

The sitting room at Aberford holiday cottage in Reydon, Suffolk

The kitchen and dining area at Aberford holiday cottage, Reydon, Suffolk

Delightful snug room with bookcase and grey sofa, at Aberford holiday cottage

NEW

Reydon, SouthwoldAberford

Property Ref: 651658

A beautifully designed bungalow boasting stylish interiors and plenty of outdoor space, this out of town holiday home is a real haven of tranquillity.

Sleeps 4
Bedrooms 2
Bathrooms 1
Dogs 1

Price: £662 - £1,230 per week

Albany Cottage, Southwold. Lounge with fireplace and smart TV. Available to let from Durrants Holiday Cottages, Suffolk

Albany Cottage, Southwold. Double bedroom with white bedding and grey wardrobe. Available to let from Durrants Holiday Cottages, Suffolk

Albany Cottage, Southwold. Twin bedroom with two single beds. Available to let from Durrants Holiday Cottages, Suffolk

SouthwoldAlbany Cottage

Property Ref: 625792

A newly refurbished and well-equipped dog-friendly holiday cottage just off Pier Avenue, one of Southwold’s most popular residential areas.

Sleeps 5
Bedrooms 3
Bathrooms 1
Dogs 1

Price: £657 - £1,104 per week

Angel Cottage, Southwold. Charming red brick terraced cottage. Available via Durrants Holiday Cottages, Suffolk

Angel Cottage_Durrants_Southwold_sitting room

Angel Cottage_Durrants_Southwold_Kitchen

SouthwoldAngel Cottage

Property Ref: 594070

Stylish, comfortable and oh-so-cosy, you’d think Angel Cottage was sent from Heaven!

Sleeps 2
Bedrooms 1
Bathrooms 1
No Dogs

Price: £625 - £1,220 per week

A pretty, red-brick semi detatched cottage with front courtyard garden. Australis, Reydon, Suffolk

Cosy sitting room with brick fireplace and dark blue sofas. Australis is available from Durrants Holiday Cottages, Southwold.

An inviting double bedroom with crisp white bedding. Australis holiday cottage in Reydon, near Southwold, Suffolk

ReydonAustralis (formerly Ataraxia)

Property Ref: 642002

You’ll feel immediately at home at this cosy and welcoming cottage, ideal for a couple or small family.

Sleeps 4
Bedrooms 2
Bathrooms 1
No Dogs

Price: £560 - £870 per week

Sitting room with woodburner and TV at Bell Cottage, Southwold. Available to holiday let with Durrants Holiday Cottages, Suffolk.

Double bedrooms with floral curtains and white bedding at Bell Cottage, Southwold. Available to holiday let with Durrants Holiday Cottages, Suffolk.

White kitchen diner with oven and extractor at Bell Cottage, Southwold. Available to holiday let with Durrants Holiday Cottages, Suffolk.

SouthwoldBell Cottage

Property Ref: 565405

Bell Cottage is a lovely holiday choice for family holidays by the seaside. Located close to Southwold's Church, the cottage is cosy and welcomin...

Sleeps 5
Bedrooms 3
Bathrooms 1
No Dogs

Price: £670 - £1,145 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: £623 - £1,106 per week

SouthwoldCoign

Property Ref: 565394

A charming three storey townhouse in a desirable location with lovely views over Southwold's South Green.

Sleeps 5
Bedrooms 3
Bathrooms 1
Dogs 1

Price: £700 - £1,379 per week

SouthwoldCorner Cottage (The Pink House)

Property Ref: 629110

Instantly recognisable, this iconic cottage boasts wonderful views of Southwold Common from the balcony and comes with private parking.

Sleeps 3
Bedrooms 2
Bathrooms 1
No Dogs

Price: £648 - £1,371 per week

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: £690 - £1,325 per week

SouthwoldLittle Blue Cottage

Property Ref: 565374

Where happy memories are made - stay at Little Blue Cottage in Southwold and prepare for indulgence and relaxation in this recently renovated cottage....

Sleeps 6
Bedrooms 3
Bathrooms 2
Dogs 1

Price: £707 - £1,304 per week

SouthwoldLorraine's Retreat - TEST do not book

Property Ref: 574091

THIS IS A TEST PROPERTY WE USE FOR TESTING OUR WEBSITE - PLEASE DO NOT BOOK..

Sleeps 8
Bedrooms 1
Bathrooms 1
No Dogs

Price: £2,295 - £3,450 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: £646 - £1,119 per week

Reading Room Cottage, Southwold, Suffolk. Durrants Holiday Cottages

Reading Room Cottage, Lounge, Southwold, Suffolk. Durrants Holiday Cottages

Reading Room Cottage, Kitchen, Southwold, Suffolk. Durrants Holiday Cottages

SouthwoldReading Room Cottage

Property Ref: 565418

Take a trip back in time at this character-filled Grade II Listed cottage with superb sea views.

Sleeps 6
Bedrooms 3
Bathrooms 1
No Dogs

Price: £735 - £1,487 per week

SouthwoldSaffron Cottage

Property Ref: 565447

Saffron Cottage is located just opposite St Edmunds Church and just a short stroll to the beach. This cosy holiday cottage has everything you could de...

Sleeps 6
Bedrooms 3
Bathrooms 2
No Dogs

Price: £735 - £1,626 per week

Sea Mist Southwold, Durrants Holiday Cottages, Lounge

Sea Mist Southwold, Durrants Holiday Cottages, Conservatory

Sea Mist Southwold, Durrants Holiday Cottages, Kitchen

SouthwoldSea Mist

Property Ref: 626749

A ‘home-from-home’ bungalow in a peaceful location close to all the attractions of Southwold.

Sleeps 5
Bedrooms 3
Bathrooms 1
Dogs 1

Price: £790 - £1,943 per week

Seaside Cottage, Southwold is a pretty pastel cottage near the sea. Book via Durrants Holiday Cottages, Suffolk

Seaside Cottage, Southwold has a round dining table and attractive dresser. Book via Durrants Holiday Cottages, Suffolk

Seaside Cottage, Southwold. White kitchen units and sea blue walls. Book via Durrants Holiday Cottages, Suffolk

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: £749 - £1,785 per week

Cosy sofa with yellow cushions in Silver Shore holiday cottage, Southwold, available to let through Durrants Holiday Cottages

Interior of Silver Shore holiday cottage dining room in Southwold, showcasing a table surrounded by chairs for dining

Silver Shore has an open plan kitchen within the holiday home which is fully equipped with all self-catering essentials on the Suffolk Coast

NEW

SouthwoldSilver Shore

Property Ref: 650369

Spacious, stylish and just a short stroll from the High Street, this property is the perfect family holiday-home!

Sleeps 6
Bedrooms 3
Bathrooms 2
Dogs 1

Price: £777 - £2,053 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 1

Price: £646 - £1,076 per week

Spindrift, Southwold: Exterior view of this High Street holiday home, available to let from Durrants Holiday Cottages, Suffolk

Spindrift, Southwold: Spacious lounge/diner with bay window overlooking High Street. Holiday cottage available from Durrants, Suffolk.

Spindrift, Southwold: Top floor lounge with large sofa and table football. Holiday cottage let by Durrants, Suffolk

SouthwoldSpindrift

Property Ref: 630020

This spacious and well-presented town house in the heart of Southwold boasts some of the finest panoramic views in town.

Sleeps 6
Bedrooms 3
Bathrooms 1
No Dogs

Price: £700 - £1,422 per week

Stuckie Ben, Southwold, Durrants Holiday Cottages - Exterior

Stuckie Ben, Southwold, Durrants Holiday Cottages - Lounge

Stuckie Ben, Southwold, Durrants Holiday Cottages - Dining Room

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: £686 - £1,402 per week

Sully's Cove holiday apartment, Southwold: Comfortable sofas and coffee table. Let via Durrants, Suffolk.

Sully's Cove holiday apartment, Southwold: Spacious master bedroom with jade feature wall. Let via Durrants, Suffolk

Sully's Cove holiday apartment, Southwold: White modern kitchen. Let via Durrants, Suffolk

SouthwoldSully's Cove

Property Ref: 592394

A stylishly furnished, luxury first floor apartment on one of Southwold’s most desirable streets.

Sleeps 4
Bedrooms 3
Bathrooms 1
No Dogs

Price: £653 - £1,448 per week

Vicary's House, Sitting room, Southwold, Durrants Holiday Cottages

SouthwoldVicary's House

Property Ref: 585971

Space, style, location and parking; Vicary's House is a popular family holiday home that ticks all the boxes – it’s pet-friendly too!

Sleeps 7
Bedrooms 4
Bathrooms 3
Dogs 2

Price: £1,081 - £2,389 per week

SouthwoldWherry Cottage

Property Ref: 590819

A beautifully presented holiday home offering comfort, space and a great location!

Sleeps 8
Bedrooms 3
Bathrooms 3
Dogs 1

Price: £819 - £1,607 per week

May Half Term Holidays

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