October Half Term Holidays on the Suffolk Coast with Durrants Holiday Cottages

October Half Term Holidays

The first term back to school can be the most exhausting.  Children and parents have to get used to the routine once again after the long summer break dealing with uniforms, packed lunches and homework.  It’s no wonder so many people look forward to a change of scene and complete break from the norm with an October half term holiday.

Whilst many of our holiday homes are already booked for this October half term we still have some great properties available. The cottages below are all in Southwold and the surrounding area and are available from 2 – 7 night stays arriving on Friday 24th or Saturday 25th October 2025.  Booking is available online or you can give our friendly team a call on 01502 723292.  

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65 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: £690 - £1,178 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: £690 - £1,294 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
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 - £1,266 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: £691 - £1,299 per week
Southwold24 South Green
Property Ref: 565415
Location, location, location! 24 South Green is a traditional Southwold cottage in prime position.
  • Sleeps 7
  • Bedrooms 4
  • Bathrooms 2
  • Dogs 1
Price: £977 - £1,750 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: £1,052 - £2,218 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: £651 - £1,215 per week
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: £584 - £1,565 per week
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 - £1,529 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: £640 - £1,094 per week
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: £796 - £1,401 per week
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 - £1,248 per week
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: £655 - £1,107 per week
WalberswickAldebaran
Property Ref: 565421
A spacious Walberswick holiday home which is also pet-friendly! Ideal for family breaks exploring the Suffolk coastline.
  • Sleeps 12
  • Bedrooms 5
  • Bathrooms 2
  • Dogs 4
Price: £1,274 - £2,941 per week
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: £626 - £1,221 per week
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 - £883 per week
SouthwoldBalimore
Property Ref: 565406
Just moments from Southwold's seafront, Balimore is a large family holiday home boasting views of the sea from the first floor.
  • Sleeps 8
  • Bedrooms 4
  • Bathrooms 2
  • No Dogs
Price: £1,066 - £2,244 per week
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: £678 - £1,142 per week
SouthwoldBittern Cottage
Property Ref: 565434
Bittern Cottage has it all - desirable Southwold location, pet-friendly and comes with plenty of added extras for your coastal getaway.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1
  • Dogs 1
Price: £672 - £1,152 per week
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 - £960 per week
WalberswickBuntings
Property Ref: 637375
This delightful three-bedroom holiday home in the heart of Walberswick offers, style, space, convenience and character and is ideal for two couples or...
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 2
  • No Dogs
Price: £769 - £1,700 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: £690 - £1,248 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: £618 - £1,108 per week
SouthwoldCobblestones
Property Ref: 594063
Brimming with character and comfort, Cobblestones is tucked away in a secluded courtyard in the heart of Southwold.
  • Sleeps 5
  • Bedrooms 4
  • Bathrooms 1
  • No Dogs
Price: £976 - £2,308 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 - £1,369 per week
Reydon, SouthwoldDovedale
Property Ref: 576231
A family-friendly holiday cottage ideal for breaks in all seasons. Dovedale is the perfect holiday escape with everything you could desire for a self-...
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 1
  • No Dogs
Price: £547 - £900 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: £854 - £1,993 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: £680 - £1,292 per week
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: £916 - £2,136 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: £680 - £1,326 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: £929 - £2,114 per week
NEW
SouthwoldLandlords Cottage
Property Ref: 654014
This charming and cosy cottage enjoys a central location just a short stroll to the High Street and beach.
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 1
  • No Dogs
Price: £628 - £1,392 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 - £1,326 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
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: £866 - £2,039 per week
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: £714 - £1,500 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: £654 - £1,181 per week
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: £954 - £2,092 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: £937 - £2,201 per week
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: £670 - £1,517 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 - £1,122 per week
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 - £1,490 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 - £1,629 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: £756 - £1,780 per week
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: £805 - £1,944 per week
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 - £1,790 per week
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: £787 - £2,053 per week
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: £1,366 - £3,003 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: £645 - £1,076 per week
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
SouthwoldSpyglass
Property Ref: 626184
Sat in prime position on East Cliff, this character cottage boasts stunning views of the beach, pier and beyond.
  • Sleeps 5
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 1
Price: £898 - £2,045 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: £716 - £1,352 per week
SouthwoldStrathmore
Property Ref: 565398
A particularly spacious ground floor Southwold apartment with splendid views of the sea
  • Sleeps 8
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 1
Price: £768 - £1,954 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: £686 - £1,402 per week
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
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 - £3,444 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: £637 - £1,204 per week
NEW
SouthwoldThe Perch
Property Ref: 644843
A luxurious haven of tranquillity and style where guests can enjoy the natural beauty of Southwold.
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £872 - £2,222 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: £704 - £1,315 per week
SouthwoldWaimana
Property Ref: 565417
A unique Southwold holiday home tucked away in a quiet spot, Waimana is a popular choice for families or friends looking to escape to the Suffolk coas...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £642 - £1,549 per week
SouthwoldWestbury House
Property Ref: 565388
Westbury House is a large holiday home boasting one of the best positions in Southwold and has incredible views over South Green towards the sea
  • Sleeps 10
  • Bedrooms 5
  • Bathrooms 3
  • Dogs 1
Price: £1,385 - £2,925 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: £647 - £1,190 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
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: £647 - £1,285 per week

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