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What's on in Dorset in September 2025

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As we wrap up an exciting September in Dorset, with its harvest festivals, countryside walks, and crisp autumn air, we’d like to thank everyone who joined in the fun! While this year’s calendar is coming to a close, we’re already gearing up for an even more thrilling 2025. Stay tuned for next year’s itinerary of must-see events and special offers. Do you want to keep up-to-date with what’s on in September in Dorset this year and the next? Our email newsletter will keep you up-to-date with the ins and outs of our lovely coastal county, including upcoming events, our favourite attractions and landmarks, and our latest accommodation offers. Sign up today and be the first to hear about what’s happening in 2025!

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Find a September

Holiday Cottage in Dorset

Seaspray image
Seaspray
Swanage
5/5
Located steps away from the sandy beach and traditional promenade in Swanage, Seaspray is a three-bedroom, 1930s-style apartment with panoramic sea views. Situated on the wonderful seafront parade, this town centre location is perfect for families or friends seeking a relaxing coastal escape within a stone’s throw of many of Dorset’s prolific attractions.
5
3
2
0
19th - 26th September  £873.25
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Stone Quay Cottage image
Stone Quay Cottage
Swanage
4.9/5
Stone Quay Cottage is right in the heart of the beautiful old fishing town of Swanage, just a stones throw away from the historic Stone Quay, the lovely sandy beaches, the Victorian Pier and all the amenities. This two bedroom cottage dates back to the 1850’s but has been completely renovated to provide a beautiful modern home.
3
2
1
2
28th - 30th September  £285.00
25th - 29th September  £555.00
1st - 14th September  £1,975.00
+263 more stays
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Malvern Apartment
Swanage
4.5/5
This appealing large, ground floor apartment is part of a modern conversion of a former Edwardian hotel, right in the heart of the seaside town of Swanage in a quiet residential, tree lined street, less than 5 mins walk to restaurants, pubs, shops and the beach. You can enjoy a lovely glimpse view across Swanage bay from the lounge bay window.
2
1
1
0
27th - 30th September  £366.97
13th - 20th September  £535.15
13th - 26th September  £921.45
+12 more stays
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The Wedge image
The Wedge
Swanage
4.9/5
A spacious 3 bedroom bungalow, set on the cliff top in a private part of Swanage overlooking picturesque Purbeck Hills. Situated just outside of the town centre on a quiet road but with all amenities nearby, this holiday home is within a short walk of the beach. It is ideal for those wishing to explore most spectacular walks and enjoy the scenery of a pretty coastline.
6
3
2
1
28th - 29th September  £674.58
26th - 27th September  £674.58
26th - 29th September  £761.71
+12 more stays
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St Marks Cottage image
St Marks Cottage
Swanage
5/5
Come and stay in this beautifully appointed cottage, ideal for families and cottage in a quiet spot in the town - walk to beach and coastal path.
4
2
2
0
23rd - 26th September  £725.69
12th - 25th September  £1,933.75
19th - 25th September  £988.75
+73 more stays
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Leap House
Wareham
5/5
Leap House is a well-presented three-bedroom semi-detached holiday retreat, sitting peacefully within a short walk of Wareham Quay. This well-presented holiday accommodation, is an excellent base to explore one of England’s Saxon Walled towns and nearby beaches of the Jurassic coast. Entering the house via the patio area, you will be greeted by a fully-equipped kitchen, featuring integrated appliances and all the amenities for your culinary creations, which you can enjoy in the next-door lounge/dining area. The inviting living area features two leather sofas, an armchair, and a wood-burning stove – ideal for those wanting to unwind with a book or a favourite movie.
4
3
1
0
12th - 19th September  £734.65
12th - 26th September  £1,419.30
19th - 26th September  £734.65
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Brook Cottage image
Brook Cottage
Corfe Castle
4.8/5
Step back in time and enjoy this delightful semi-detached cottage, exuding charm and character throughout. Built in the early 1730s, this distinctive Grade II red bricked cottage, is set in the heart of the historic village of Corfe Castle. This cosy retreat, nestled in the heart of the Purbecks, would surely be able to tell a tale or two! Sitting peacefully at the bottom of the romantic Castle ruins, you will enjoy morning coffee with arguably one of the most impressive backdrops in Dorset.
6
3
3
0
19th - 26th September  £1,016.05
12th - 26th September  £2,036.70
12th - 19th September  £1,070.65
+2 more stays
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Juniper Cottage image
Juniper Cottage
West Lulworth
4.9/5
Juniper Cottage is a recently refurbished Victorian terraced cottage tucked away off the main road in the scenic village of West Lulworth, close to both Lulworth Cove and one of the Jurassic Coast’s most iconic features, Durdle Door. This two-storey, dog-friendly cottage accommodates up to 4 adults or a family of 5. The ground floor is an open-plan living and dining space with small, private front and rear gardens, upstairs are two bedrooms and a bathroom.
5
2
1
2
26th - 29th September  £591.55
19th - 30th September  £1,245.00
12th - 26th September  £1,728.00
+12 more stays
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Coastguard Cottage image
Coastguard Cottage
Worth Matravers
4.6/5
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
8
4
3
0
19th - 26th September  £854.35
12th - 26th September  £1,658.70
12th - 19th September  £854.35
+2 more stays
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Winspit View
Worth Matravers
4.8/5
3 Bedrooms. The bungalow is located on the edge of the village of Worth Matravers, in a rural idyll with fantastic views across open farmland to Winspit and the sea. A lovely holiday cottage to rent in Worth Matravers, an exclusive village in Dorset.
6
3
2
1
19th - 26th September  £1,091.65
12th - 26th September  £2,133.30
12th - 19th September  £1,091.65
+2 more stays
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1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
3 bedrooms. A distinctive period holiday cottage to rent in Wareham, in a unique location with tastefully presented interior. This is one of only three cottages built on top of the old Saxon walls in Wareham.
5
3
2
0
27th - 30th September  £619.14
26th - 28th September  £619.14
27th - 29th September  £619.14
+4 more stays
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Heathlands image
Heathlands
Studland
4.6/5
3 bedrooms. Heathlands is a modern cottage, the ideal base for family holidays in Studland. This light and airy holiday home is a short walk from Studlands long sandy beach.
6
3
1
0
20th - 27th September  £789.25
13th - 27th September  £1,582.05
13th - 20th September  £842.80
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Purbeck Escape image
Purbeck Escape
Swanage
4.7/5
3 Bedrooms. Super reviews for this recent addition to our holiday homes. Purbeck Escape is a spacious, newly equipped family home.
6
3
2
0
20th - 27th September  £724.15
13th - 27th September  £1,398.30
13th - 20th September  £724.15
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Orchid House image
Orchid House
Langton Matravers
4.9/5
A delightful four-bedroom holiday accommodation, set right on the doorstep of Dorset’s most breath-taking coastal walks, in the village of Langton Matravers.
8
4
3
2
19th - 26th September  £1,141.00
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White Sands image
White Sands
Swanage
4.9/5
4 Bedrooms. This stunning property is set on the cliff top in a secluded part of Swanage, boasting panoramic sea views over the bay toward Peveril Point, the Isle of Wight and Ballard Down. Situated just outside of the town centre and well away from any main road, it is beautifully quiet, ideal for those of you wishing to escape it all.
9
4
2
2
20th - 27th September  £1,639.75
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Dream Cottage image
Dream Cottage
Portland
5/5
A stylish, compact cottage - ideal for friends and small families to get together to enjoy the coast, walking and watersports.
6
3
2
0
28th - 29th September  £481.80
5th - 15th September  £1,561.87
18th - 29th September  £1,471.20
+312 more stays
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Lizards Rest image
Lizards Rest
Swanage
4.7/5
4 bedrooms. A great base and comfortable family home. This substantial detached holiday home offers ample accommodation for the extended family in a seaside location. Lizards Rest is the perfect choice for accommodation for large groups in Swanage.
9
4
2
0
27th - 30th September  £537.90
27th - 29th September  £537.90
28th - 30th September  £537.90
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Below Decks image
Below Decks
Swanage
4.8/5
Below Decks is a gorgeous, seafront holiday home that sleeps 6 guests. Situated on the Parade in the heart of Swanage with the main beach, restaurants and shops directly on your doorstep, it is perfect for a relaxing coastal getaway.
6
3
2
2
21st - 28th September  £746.20
14th - 21st September  £899.20
20th - 27th September  £746.20
+3 more stays
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West Lodge image
West Lodge
Church Knowle, Nr Corfe Castle
4.9/5
Tastefully presented and finished to a high standard, this fabulous holiday home in Church Knowle, will appeal to those of you visiting with extended family and friends. Located just a mile outside Corfe Castle, as the crow flies between Kimmeridge Bay and the golden sands of Studland, you will be truly spoilt for things to see and do.
10
5
3
0
26th - 29th September  £840.66
26th - 30th September  £959.05
19th - 30th September  £1,781.25
+10 more stays
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Bronte Cottage image
Bronte Cottage
Wareham
4.8/5
3 Bedrooms. Bronte Cottage is a charming holiday cottage in Wareham, hidden away in a fabulous location a few strides from Wareham Quay and the river Frome.
4
3
2
1
19th - 26th September  £659.05
5th - 12th September  £767.20
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