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Autumn Breaks in Dorset

516 properties found

A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth

The Nightingale

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Fri 16th Oct for 3 nights

£530

A window with champagne and glasses overlooking the sea at 123 On The Sea – The Eaves in Weymouth
New

123 On The Sea - The Eaves

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Sat 31st Oct for 3 nights

£385

A living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth
New

123 On The Sea - Victoria’s Place

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Mon 19th Oct for 3 nights

£385

A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth

Harbour Retreat

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

Fri 16th Oct for 3 nights

£435

A house with garage and pathway at Millmead House in Portesham

Millmead House

Portesham, Dorset

8 Guests
4 Beds
Pet Friendly
Wifi

Thu 15th Oct for 3 nights

£856

A hallway with door opening to the sea at 123 On The Sea - The Cubby in Weymouth
New

123 On The Sea - The Cubby

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Thu 15th Oct for 3 nights

£374

A living room with furniture including a sofa and a dresser at 4 The Beaches in Weymouth
New

4 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Thu 29th Oct for 3 nights

£573

An entrance with double doors and window at Frome Gazey in Frampton
New

Frome Gazey Barn

Frampton, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 23rd Oct for 3 nights

£525

An exterior view of a rustic building with tiled roof and multiple glass doors opening onto a cobblestone courtyard with potted plants and a garden area at The Shippon in Honiton
Save £211

The Shippon

Honiton, Devon

2 Guests
1 Beds
No pets
Wifi

Fri 6th Nov for 3 nights

£713

£502

An outdoor patio area with tables, chairs, and flower beds outside cream walls with blue doors and windows at The Compass in Swanage

The Compass

Swanage, Dorset

2 Guests
1 Beds
No pets
Wifi

Sun 15th Nov for 3 nights

£367

A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth

Little Brook

Nottington near Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 23rd Oct for 3 nights

£552

A garden with a table and chairs at Tipsy Turtle in Weymouth

Tipsy Turtle

Portland, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Tue 27th Oct for 3 nights

£442

A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock

Village View

Burton Bradstock, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Sat 14th Nov for 3 nights

£498

A house with solar panels and a gravel driveway at 2 North Road Maiden Newton, Dorset

2 North Road

Maiden Newton, Dorset, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Fri 16th Oct for 3 nights

£454

A living room with a sofa and coffee table at 6 Bedford Place in Bridport

No. 6

Bridport, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Sat 17th Oct for 3 nights

£466

An outdoor pathway with flower pots and brick walls at The Sunday School Room in Sherborne
New

The Sunday School Room

Glanvilles Wootton, Dorset

2 Guests
1 Beds
No pets
Wifi

Sun 18th Oct for 3 nights

£350

A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock

Cliff Barn

Burton Bradstock, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Tue 10th Nov for 3 nights

£515

A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere

The Folly at Castlebridge

Mere, Wiltshire

2 Guests
1 Beds
Pet Friendly
Wifi

Sat 7th Nov for 3 nights

£557

A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth

5 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Thu 29th Oct for 3 nights

£503

An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth

Fountain Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 16th Oct for 3 nights

£511

Enjoy crisp coastal walks, cosy countryside evenings and peaceful villages wrapped in colour by booking one of these cottages for autumn breaks in Dorset. 

Why Book Autumn Breaks in Dorset? 

When the summer crowds fade and the leaves begin to turn, there’s something truly special about autumn holidays in Dorset. From the rolling hills of the countryside to the dramatic cliffs of the Jurassic Coast, this time of year brings a sense of calm that makes it ideal for a peaceful break. 

Staying in one of these autumn holiday cottages in Dorset allows you to explore a wide range of charming towns and pretty villages without the hustle and bustle of peak season. Whether you’re admiring the golden glow of the woodlands or walking along near-empty beaches, autumn is a fantastic time to soak up the best of the region. 

What’s more, these properties are fully equipped for comfort and warmth, offering a relaxing base after a day of exploration. Whether you're enjoying a romantic getaway, a family half-term escape or simply need some time to unwind, booking one of these autumn breaks in Dorset is the perfect way to recharge. 

Places to Visit during Autumn Holidays in Dorset 

If you’re booking an autumn break in Dorset, you’ll find a brilliant range of places to explore right on your doorstep. 

One popular spot is Lyme Regis, found on the county’s western edge and just a short 25-minute drive from many of these properties. Famed for its fossil-rich beaches and charming town centre, it’s particularly atmospheric during the quieter autumn months. Visit the historic Cobb harbour, pop into one of the cosy cafés, or enjoy a walk along the beach wrapped up in your warmest layers. 

Another great place to visit is Swanage, located on the Isle of Purbeck around a 45-minute drive away. It’s a brilliant place for coastal hikes, with the South West Coast Path offering spectacular clifftop views. While here, take the chance to hop on the Swanage Railway for a steam train ride through the countryside, or spend a quiet afternoon exploring Durlston Country Park, a brilliant autumn spot full of natural beauty. 

Other Popular Destinations for booking Autumn Holiday Cottages in Dorset: 

Bridport 

Charmouth 

Dorchester 

Poole 

Weymouth 

Types of Dorset Holidays 

As well as this brilliant collection of cottages for autumn breaks in Dorset, there’s also a full range of Dorset holiday cottages to explore, including everything from luxury escapes to family-friendly retreats. 

Looking to bring your four-legged friend along for the fun? If so, be sure to check out these dog-friendly cottages in Dorset. Or perhaps you're after something extra special? In which case, have a look at these luxury cottages or cottages with hot tubs to help make your stay extra cosy. 

If you're planning a group trip, be sure to browse these large holiday cottages, or explore these family holidays in Dorset. Alternatively, if you're thinking of a shorter escape, these short breaks might be exactly what you’re after. 

For something a little more unique, why not explore these lodges and log cabins or glamping pods in Dorset? And if you’re planning something romantic, these romantic cottages are ideal for couples looking to enjoy some quality time together. 

Still looking for a great deal? Don’t forget to check out these last-minute offers. 

Found the perfect place to book for your next Autumn break in Dorset? If so, then what are you waiting for? Book online or get in touch with Dream Cottages today and start planning your next getaway! 

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