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 for a seven night break arriving on Friday 25th or Saturday 26th October 2024.  Booking is available online or you can give our friendly team a call on 01502 723292.  

62 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
NEW
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: £660 - £1,160 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
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: £855 - £1,650 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
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: £740 - £1,525 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: £635 - £1,365 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
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: £640 - £1,395 per week
Southwold9 Salisbury Road
Property Ref: 594620
Space, style and luxury reside at this beautifully furnished holiday home in prime position in Southwold.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 3
  • No Dogs
Price: £1,075 - £2,845 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: £650 - £1,195 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: £1,095 - £2,615 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: £950 - £2,225 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: £640 - £1,065 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: £625 - £1,265 per week
NEW
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
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
SouthwoldChurch Green Cottage
Property Ref: 565448
Church Green Cottage is a lovely holiday cottage just a short walk to the seafront and High Street shops and boasts views of Southwold's Lighthou...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £650 - £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
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: £715 - £1,785 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 - £1,095 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: £535 - £1,050 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: £735 - £1,735 per week
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: £1,125 - £2,175 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
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: £735 - £1,445 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
Reydon, SouthwoldJubilee View
Property Ref: 565395
For lovers of coast and countryside, Jubilee View is located in the village of Reydon just a three minute drive from the coastal town of Southwold.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 2
  • No Dogs
Price: £565 - £1,140 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
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: £670 - £1,425 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: £965 - £2,120 per week
SouthwoldMarshfields
Property Ref: 625479
A real home from home, Marshfields offers comfortable, spacious accommodation and wonderful marsh views.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 1
Price: £795 - £1,695 per week
NEW
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
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 - £1,275 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
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: £675 - £1,450 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
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: £685 - £1,480 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
SouthwoldSeaway House
Property Ref: 565427
Seaway House is located in the centre of Southwold therefore just a short walk to the seafront and High Street shops. This holiday cottage is comforta...
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 2
  • No Dogs
Price: £615 - £1,225 per week
NEW
SouthwoldSkylark
Property Ref: 638953
COMING SOON! This fabulous 4-bedroom family holiday home is currently being refurbished and will be available from Summer 2024.
  • Sleeps 8
  • Bedrooms 4
  • Bathrooms 2
  • Dogs 1
Price: £955 - £2,400 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
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: £685 - £1,495 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: £850 - £1,785 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
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: £615 - £1,165 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: £1,125 - £2,650 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 Retreat
Property Ref: 594176
A well-appointed ground-floor apartment close to Southwold Common suitable for those with mobility issues.
  • Sleeps 2
  • Bedrooms 1
  • Bathrooms 1
  • No Dogs
Price: £490 - £740 per week
SouthwoldThe Sanderling
Property Ref: 588103
A bright and contemporary holiday home for 6 adults and 2 children, The Sanderling is offers open-plan, modern living in the heart of Southwold.
  • Sleeps 8
  • Bedrooms 4
  • Bathrooms 3
  • No Dogs
Price: £1,115 - £2,485 per week
SouthwoldToad Hall
Property Ref: 565399
Toad Hall is a character cottage tucked away in a hidden spot close by to Southwold's South Green area.
  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 2
  • Dogs 1
Price: £630 - £1,590 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 - £1,315 per week
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: £925 - £2,415 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
SouthwoldWherry Cottage (Sleeps 4)
Property Ref: 631328
A beautifully presented and spacious holiday home offering comfort, space and a superb location!
  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 3
  • Dogs 1
Price: £680 - £1,410 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: £845 - £2,010 per week

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