Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 678 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights €613

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights €780

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €443

  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €1358

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A detached barn conversion set within the village of Long Bredy. Woodburning fire. WiFi. Weymouth 12 miles; Yeovil 20 miles. (Ref. 998739)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €661

Last booked yesterday
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  • Sleeps13
  • Bedrooms6
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • Sky TV


for 7 nights €2458

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Easter Weekend open to book! A characterful first-floor apartment set on the Dorset coast, within the town of Weymouth. Outstanding sea views. Central location. Family-friendly. Isle of Portland 7 miles; Dorchester 7.2 miles; West Bay 18.1 miles. (Ref. 1049890)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €996

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €923

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €687

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights €933

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Comfortable cottage for couples or small family in Nottington, Dorset. Beaches and historic harbour 3 miles. Wifi. Lawn garden. Wheelchair access. (Ref. 994199)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €588

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €739

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights €659

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles (Ref. 1165359)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights €411

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Trinity Lodge is a striking rural holiday home with great attention to detail, within the Dorset National Landscape, in Goodmanstone, near Cerne Abbas. Dorchester 5.3 miles; Weymouth 14 miles; Sherborne 14.3 miles; Yeovil 17.4 miles. (Ref. 1149594)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights €506

  • Sleeps8
  • Bedrooms5
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Glyde House is a detached property situated in Dorchester, Dorset. Close to a shop and a pub. Off-road parking. Garden. Near Dorset AONB. Weymouth 8.6 miles; Isle of Portland 14.7 miles. (Ref. 1150284)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • €184 off - Sat 14th Mar to 21st Mar 2026


for 7 nights €958

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights €698

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights €985

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €558

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights €847

Looking for somewhere to stay in the heart of Dorset? If so, then booking accommodation in Dorchester is a brilliant option to consider. With a mix of countryside charm and historic character, it’s the perfect spot for your next getaway.

Why Book Accommodation in Dorchester, Dorset?

Dorchester is a lovely market town found in the very centre of Dorset, steeped in history and full of character. As the county town, it’s known for its rich Roman heritage, with a range of fascinating attractions including the remains of a Roman townhouse and the town’s ancient walls.

Aside from its history, Dorchester also boasts a bustling town centre with shops, museums and a regular market that draws in locals and visitors alike. You’ll find plenty of great places to eat and drink here, from cosy pubs to charming cafés.

These Dorchester holiday homes also put you within easy reach of Dorset’s National Landscape boasting picturesque countryside and beautiful coastline. And with a train station resting in the middle of the town, you have easy access to many other pretty spots along the coast too.

So, whether you’re after relaxing walks, beach days, or simply a great location to unwind in, these cottages in Dorchester tick all the boxes.

Places to Visit from your Accommodation in Dorchester, Dorset

There’s plenty to see and do just a short drive from your accommodation in Dorchester, Dorset.

For a traditional seaside experience, take a 20-minute drive south to the coastal town of Weymouth. With its golden beach, charming promenade and bustling harbour, it’s a fantastic place for a family day out. If you have time, stop by Nothe Fort or take a stroll along the South West Coast Path for spectacular sea views. For those that wish to test their swing, be sure to check out one of the gold courses on the outskirts of the town.

Alternatively, visit the lovely village of Wool, also accessible by train. It's a great base for exploring the nearby Lulworth Cove and Durdle Door, two of the most iconic landmarks along the Jurassic Coast. Along the way, enjoy scenic drives through the Dorset countryside and stop off at local farm shops or cafés for a bite to eat.

For more ideas on what to do during your escape, be sure to check out this excellent Dorset Travel Guide.

Other Popular Destinations for booking Dorchester Holiday Homes:

Bournemouth

Poole

Swanage

Wareham

West Bay

Types of Dorset Holidays

As well as this fantastic selection of accommodation in Dorchester, there’s also a full collection of all Dorset holiday cottages to explore. If you're planning a large group getaway, these large cottages in Dorset are well worth a look.

Or, if you'd prefer to experience rural charm, don’t miss these farm cottages in Dorset or these log cabins in Dorset. Looking to stay close to the sea? Be sure to check out these coastal cottages in Dorset too.

Planning something extra-special? Then browse these luxury Dorset cottages or book one of these hot tub cottages in Dorset for added comfort.

There are also plenty of dog-friendly cottages in Dorset for those bringing their pooch along, or if you’re looking to escape soon, these last-minute cottages and short breaks in Dorset may be ideal.

Prefer something different? Then explore these unique glamping pods in Dorset or even a relaxing stay in one of these cottages with swimming pools. And for family fun, take a look at these family-friendly Dorset holidays too.