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.

51 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: £651 - £1,239 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

NEW

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

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: £665 - £1,239 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: £672 - £1,236 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: £615 - £1,260 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: £700 - £1,559 per week

33 Victoria Street-Southwold-Durrants-Exterior

33 Victoria Street-Southwold-Durrants-fireplace

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: £735 - £1,439 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: £609 - £1,239 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: £777 - £1,376 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: £651 - £1,142 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: £595 - £1,384 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 - £955 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: £637 - £1,189 per week

Briar Cottage, Westleton, Suffolk. A pretty cream cottage with garden and patio

The cosy sitting room at Briar Cottage, Westleton, Suffolk

A cream and wood, galley style kitchen at Briar Cottage, Westleton

WestletonBriar Cottage

Property Ref: 639850

A cosy cottage in the picturesque village of Westleton, ideally located for visiting RSPB Minsmere and National Trust Dunwich Heath.

Sleeps 3
Bedrooms 2
Bathrooms 1
Dogs 2

Price: £525 - £765 per week

Buntings, Walberswick. Attractive sitting room with colourful chair and sofa and glass table. Holiday let via Durrants Holiday Cottages, Suffolk

Buntings, Walberswick. Bedroom with neutral colour palette and kingsize bed Holiday let via Durrants Holiday Cottages, Suffolk

Buntings, Walberswick. Double bedroom with cream walls, white bedding and patterned cushions. Holiday let via Durrants Holiday Cottages, Suffolk

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: £798 - £1,651 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: £616 - £1,123 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: £665 - £1,364 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: £595 - £1,284 per week

SouthwoldEastholme

Property Ref: 586886

This lovely cottage has been completely renovated and extended making it a luxurious home in the heart of Southwold.

Sleeps 6
Bedrooms 3
Bathrooms 2
No Dogs

Price: £805 - £2,250 per week

SouthwoldFairwinds

Property Ref: 565385

Boasting sea views, private parking and a fabulous location on South Green, this simply furnished first floor flat is very popular.

Sleeps 4
Bedrooms 2
Bathrooms 1
No Dogs

Price: £595 - £1,309 per week

Ferryway, a modern timber home by the sea at Southwold, Suffolk. Holiday let with Durrants Holiday Cottages.

Open plan living area with woodburner at Ferryway, Southwold, Suffolk

Contemporary kitchen with built in appliances at Ferryway, Suffolk.

NEW

SouthwoldFerryway

Property Ref: 638687

Fabulous design and breathtaking location are combined here to create a holiday home with a difference.

Sleeps 4
Bedrooms 2
Bathrooms 2
No Dogs

Price: £1,120 - £2,772 per week

High View_Durrants_Southwold_view from master bedroom

High View_Durrants_Southwold-bedroom two

High View_Durrants_Southwold-sitting room

SouthwoldHigh View

Property Ref: 590257

A spacious Edwardian apartment on Southwold High Street with stunning views from its balcony plus off-road allocated parking. TWO-NIGHT STAYS AVAILABL...

Sleeps 4
Bedrooms 2
Bathrooms 2
No Dogs

Price: £633 - £1,602 per week

Holly House - Lounge, Durrants Holiday Cottages, Southwold

Holly House - Exterior, Durrants Holiday Cottages, Southwold

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: £889 - £2,109 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: £798 - £1,463 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: £672 - £1,267 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: £715 - £3,450 per week

Lushan, Walberswick, Suffolk, Durrants Holiday Cottages

Sitting Room, Lushan, Walberswick, Suffolk

Superking or Twin Bedroom, Lushan, Walberswick, Suffolk

WalberswickLushan

Property Ref: 585938

A place where family memories are made, Lushan is a heavenly 3 bedroom period property in a tucked away part of Walberswick.

Sleeps 6
Bedrooms 3
Bathrooms 2
Dogs 2

Price: £1,015 - £1,930 per week

Millie's Lodge, 9 St Edmunds Road, Southwold - Lounge

Millie's Lodge, 9 St Edmunds Road, Southwold - Fireplace

Millie's Lodge, 9 St Edmunds Road, Southwold - Dining area

SouthwoldMillie's Cottage

Property Ref: 592086

Insta-worthy interior design! Millie's Cottage is beautifully bespoke nestled in a lovely area of Southwold.

Sleeps 4
Bedrooms 2
Bathrooms 2
Dogs 1

Price: £665 - £1,407 per week

Nuage_Durrants_Southwold_View from sitting room

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 - £1,195 per week

Number 5 in Southwold, let by Durrants Holiday Cottages

Southwold, SuffolkNumber 5

Property Ref: 591510

This exceptional holiday bungalow has it all – stylish and comfortable accommodation, magnificent views, superb location just steps from the bea...

Sleeps 4
Bedrooms 2
Bathrooms 1
Dogs 2

Price: £903 - £1,869 per week

SouthwoldNumber Fifteen

Property Ref: 639851

A haven of luxury, Number Fifteen offers high quality, stylish accommodation in the heart of Southwold.

Sleeps 6
Bedrooms 3
Bathrooms 2
No Dogs

Price: £1,150 - £2,295 per week

WalberswickOld Post Office Cottage

Property Ref: 581045

Old Post Office Cottage is a charming, cosy cottage only a few steps away from the harbour and the beach. The ideal seaside retreat for a couple or a ...

Sleeps 3
Bedrooms 2
Bathrooms 1
Dogs 1

Price: £553 - £1,245 per week

Palmer's Cottage_Durrants_Southwold_Sitting Room view 2

Palmer's Cottage_Durrants_Southwold_Dining Kitchen

Palmer's Cottage_Durrants_Southwold_Front exterior

SouthwoldPalmer's Cottage

Property Ref: 599766

You’ll feel immediately at home at this beautifully renovated character cottage.

Sleeps 4
Bedrooms 2
Bathrooms 2
Dogs 1

Price: £735 - £1,595 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: £637 - £1,098 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 - £1,035 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: £714 - £1,484 per week

Sandy Castle, Southwold, Durrants Holiday Cottages - sitting room

Sandy Castle, Southwold, Durrants Holiday Cottages - dining room

Sandy Castle, Southwold, Durrants Holiday Cottages - bedroom

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: £714 - £1,641 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: £693 - £1,821 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: £725 - £1,625 per week

An attractive bay fronted red brick cottage, Skylark Southwold is available from Durrants Holiday Cottages, Suffolk

Bright, traditional sitting room with character fireplace and wall-mounted smart TV at Skylark, Southwold

Bright en suite bedroom with large bay window overlooking the park at Skylark, Southwold.

NEW

SouthwoldSkylark

Property Ref: 638953

Skylark is a fabulous and recently refurbished dog-friendly holiday home located in the heart of Southwold.

Sleeps 8
Bedrooms 4
Bathrooms 3
Dogs 1

Price: £1,265 - £2,546 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: £644 - £1,060 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: £721 - £1,471 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: £651 - £1,445 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: £616 - £1,200 per week

Thalassa, Walberswick, Durrants, Sitting Room

Thalassa, Walberswick, Durrants, Kitchen

WalberswickThalassa

Property Ref: 609999

Wonderfully Walberswick! This big, bold holiday home is the perfect place to make memories to treasure with family and friends.

Sleeps 8
Bedrooms 4
Bathrooms 2
Dogs 1

Price: £1,485 - £3,064 per week

The Old Bakery, holiday cottage for two, Southwold, Durrants, Lounge 1

The Old Bakery, holiday cottage for two, Southwold, Durrants, Bedroom 3

The Old Bakery, holiday cottage for two, Southwold, Durrants, Kitchen 1

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 - £1,313 per week

WalberswickThe Sheiling

Property Ref: 565413

The Sheiling is a pet-friendly single-storey cottage nestled in the popular seaside village of Walberswick. Ideal for those looking to explore the Suf...

Sleeps 6
Bedrooms 3
Bathrooms 2
Dogs 1

Price: £765 - £1,645 per week

SouthwoldTookey

Property Ref: 565381

Unique and luxurious Southwold holiday cottage just a stone's throw from Southwold's bustling High Street and glorious Common

Sleeps 4
Bedrooms 2
Bathrooms 2
No Dogs

Price: £655 - £1,355 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: £1,014 - £2,384 per week

SouthwoldWherry Cottage (Sleeps 8)

Property Ref: 590819

A beautifully presented holiday home offering comfort, space and a great location! Reduced occupancy discount available.

Sleeps 8
Bedrooms 3
Bathrooms 3
Dogs 1

Price: £777 - £1,867 per week

Lounge area with views of garden, Wood End in Reydon, Suffolk

Lawned garden at Wood End Reydon, near Southwold, Suffolk

Double bedroom with nautical theme. Wood End, Reydon.

NEW

ReydonWood End

Property Ref: 644883

The perfect combination of rural retreat and seaside escape, Wood End is a luxury home in a peaceful setting just a short drive from Southwold.

Sleeps 4
Bedrooms 2
Bathrooms 2
Dogs 2

Price: £644 - £1,559 per week

May Half Term Holidays

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