Cottages sleeping two people in Dorset

Pop into Dorset for Hardy-esque holidays and write your own love story in a holiday cottage sleeping two people.

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Although providing the perfect bolt-hole, plentiful days out for a pair are readily available from your Dorset cottage’s doorstep. A romantic break for two is just the ticket.

The region is imbued with romantic ruins and icons of the region’s mythological past – perfect for investigating with a friend or partner. Take a look at castles such as Lulworth, or the majestic Sherbourne Abbey.  Or step even further back in time: climb up the Iron Age hill-forts overlooking the River Stour or explore sites associated with Celtic mythology such as Badbury Rings, Maiden Castle, Knowlton Circles and the Cerne Giant.

It’s not only the man-made architecture and which is revered in the county: the iconic Old Harry Rocks and the impressive Durdle Door are equally as stunning. Pack a picnic full of local produce and head along the coastal path to best appreciate these natural wonders. 

For more seaside adventures for two, Hengitsbury Head is the ideal spot for a sunset stroll. Chat with fishermen reeling in the day’s catch, then climb the hill to receiving stunning panoramic views. Although you won’t want to try Chesil Beach’s full 18-mile length, stroll along this impressive spit for a different perspective on the Portland coast. Then head to Wyke Regis to soak up the village’s relaxed ambience or gorge on oysters and the freshest fish with a cooling white tine at one of its famed coastal restaurants. For added luxury on your seaside break, why not choose a holiday cottage with a hot tub for extra relaxation while away.

Dorset’s literary son, Thomas Hardy, used the county as a back-drop for many of his novels, so inspiriting to him were its hills, rivers and towns. Pull on your hiking boots and explore the Blackmoor Vale, north of Hardy’s home town – the pretty Dorchester. Hardy waxes lyrical on the area, stating that, “Here in the valley, the world seems to be constructed upon a smaller and more delicate scale…The atmosphere below is languorous…and the horizon beyond is of deepest ultramarine.' With recommendations such as this, how can you not explore the area?

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We have 43 self catering cottages in Dorset that sleeps two.

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Location

Facilities

Property

Children

 
  • The Linhay - Holiday Cottage - 2.3 miles W of Bridport
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    | 2661

     
    1 bedroom, rural cottage near the beach near Bridport, Dorset.
    Sleeps 2 + cotSaturday changeover
    Regret no petsPrice per week £301 - £580
    The Linhay is a tucked away single-storey retreat – an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel ...
     
    50.7277
    -2.8097
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2661/26610129.jpg?w=236&h=157&mode=crop&v=2
    The Linhay (2661)
    Sleeps 2 + cot
  • The Dairy - Holiday Cottage - 2.3 miles W of Bridport
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    | 2663

     
    1 bedroom, rural cottage near the beach near Bridport, Dorset.
    Sleeps 2 + cotSaturday changeover
    Regret no petsPrice per week £301 - £580
    The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French windows to its own enclosed outside space – ...
     
    50.7277
    -2.8098
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2663/26630127.jpg?w=236&h=157&mode=crop&v=635272070536178750
    The Dairy (2663)
    Sleeps 2 + cot
  • Owl's Nest Cottage - Holiday Cottage - 6.2 miles E of Sherborne
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    | 2942

     
    1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.
    Sleeps 2Friday changeover
    Dogs welcome (1 only)Price per week £301 - £585
    This cosy, compact yet delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in ...
     
    50.9488
    -2.4008
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2942/29420033.jpg?w=236&h=157&mode=crop&v=0
    Owl's Nest Cottage (2942)
    Sleeps 2
  • Badgers Cottage - Holiday Cottage - 3.8 miles E of Bridport
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    | 3014

     
    1 bedroom, dog friendly self catering cottage near Bridport, Dorset.
    Sleeps 2 + cotFriday changeover
    Dogs welcomePrice per week £301 - £595
    Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design is light ...
     
    50.7351
    -2.6751
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/3014/30140018.jpg?w=236&h=157&mode=crop&v=1
    Badgers Cottage (3014)
    Sleeps 2 + cot
  • The Stables - Holiday Cottage - 6 miles E of Dorchester
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    | 1965

     
    1 bedroom, rural holiday cottage near Dorchester, Dorset.
    Sleeps 2 + cotFriday changeover
    Regret no petsPrice per week £317 - £710
    Dorset's World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the Owner's home, The Stables is ...
     
    50.7192
    -2.2994
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/1965/19650144.jpg?w=236&h=157&mode=crop&v=635671026989524732
    The Stables (1965)
    Sleeps 2 + cot
  • Lottie’s Loft - Holiday Cottage - 3.5 miles NW of Beaminster
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    | 2565

     
    1 bedroom, rural holiday cottage near Beaminster, Dorset.
    Sleeps 2Friday changeover
    Regret no petsPrice per week £341 - £660
    Lottie's Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with ...
     
    50.8494
    -2.7878
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2565/25650159.jpg?w=236&h=157&mode=crop&v=635603741162145799
    Lottie’s Loft (2565)
    Sleeps 2
  • The Chalet on the Beach - Holiday Cottage - Lyme Regis
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    | 3351

     
    Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.
    Sleeps 2Friday changeover
    Regret no petsPrice per week £417 - £820
    Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...
     
    50.7194
    -2.9441
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/3351/33510039.jpg?w=236&h=157&mode=crop&v=0
    The Chalet on the Beach (3351)
    Sleeps 2
  • The Old School Gables - Holiday Cottage - 8.2 miles N of Bridport
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    | 2490

     
    2 bedroom holiday cottage near Bridport, Dorset.
    Sleeps 4 + cotFriday changeover
    Regret no petsPrice per week £330 - £735
    The pretty Dorset village of Drimpton is set in lovely countryside a short drive inland from the stunning Jurassic Coast. This original school house has been converted into ...
     
    50.8424
    -2.8265
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2490/24900001.jpg?w=236&h=157&mode=crop&v=1
    The Old School Gables (2490)
    Sleeps 4 + cot
  • September Cottage - Holiday Cottage - 2.8 miles NW of Weymouth
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    | 2948

     
    2 bedroom self catering cottage near the sea near Weymouth, Dorset.
    Sleeps 4 + cotFriday changeover
    Regret no petsPrice per week £382 - £879
    This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes ...
     
    50.6249
    -2.5077
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/2948/29480032.jpg?w=236&h=157&mode=crop&v=0
    September Cottage (2948)
    Sleeps 4 + cot
  • The Old Coach House - Holiday Cottage - 9.2 miles NE of Dorchester
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    | 1386

     
    2 bedroom, rural holiday cottage near Dorchester, Dorset.
    Sleeps 4 + cotFriday changeover
    Dogs welcome (1 only)Price per week £390 - £998
    This pretty detached former coach house is in beautiful rural Dorset within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spacious bright ...
     
    50.8308
    -2.3308
    https://www.classic.co.uk/media/symbols/cottage-blue.png
    https://webpics.classic.co.uk/webpic/1386/13860153.jpg?w=236&h=157&mode=crop&v=635316175945781250
    The Old Coach House (1386)
    Sleeps 4 + cot
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We've got 43 holiday cottages matching your search criteria.


 
 

43 Holiday cottages