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Dorset Cottage Holidays, holiday homes to rent in Dorset
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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

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
27th - 30th September  £532.53
25th - 28th September  £532.53
25th - 29th September  £604.49
+60 more stays
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Compass Cottage image
Compass Cottage
Swanage
4.9/5
A boutique, contemporary seaside cottage, nestled in the heart of the town centre of Swanage.
4
2
1
1
9th - 10th September  £616.20
8th - 21st September  £1,800.38
23rd - 27th September  £794.70
+126 more stays
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Winspit View image
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
5th - 12th September  £1,091.65
5th - 19th September  £2,133.30
12th - 19th September  £1,091.65
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IMG 8040 HDR Edit
Denbur Cottage
Gaunts Common
4.8/5
2 Bedrooms. Denbur is a lovely semi-detached cottage, with lawned garden and conservatory enjoying a superb location in a village that takes its name from John O’Gaunt, Duke of Lancaster.
4
2
2
0
26th - 29th September  £469.68
19th - 27th September  £739.20
19th - 26th September  £638.05
+12 more stays
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Markham House image
Markham House
Weymouth
5/5
A spacious family home with off road parking and large, enclosed garden. The house is ideal for family and friends who want to stroll through the town to the Harbour and beach.
5
3
2
1
26th - 29th September  £718.02
19th - 29th September  £1,704.27
26th - 27th September  £718.02
+16 more stays
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Bucknowle Lodge image
Bucknowle Lodge
Church Knowle
5/5
Beautiful, spacious Dorset lodge for large parties. Within walking distance of Corfe Castle and a short drive to the coast.
8
4
3
2
28th - 29th September  £1,219.04
9th - 12th September  £1,609.17
19th - 29th September  £3,200.47
+28 more stays
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Seashell View image
Seashell View
Swanage
4.9/5
A stunning 3 bed apartment with sea views – perfect for a family beach holiday in the coastal town of Swanage, Dorset.
6
3
1
0
28th - 30th September  £559.00
20th - 29th September  £1,102.50
20th - 28th September  £990.00
+6 more stays
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Newton House image
Newton House
Swanage
4.6/5
3 bedrooms. The owners of this spacious seaside home, which is very close to Swanage beach have stylishly furnished with a contemporary and comfortable interior.
6
3
2
0
21st - 24th September  £485.01
23rd - 25th September  £485.01
13th - 25th September  £1,137.60
+16 more stays
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Hill View image
Hill View
Weymouth
5/5
Set in the peaceful Weymouth suburb of Preston, Hill View offers a delightful retreat for couples or small families.
4
2
1
1
19th - 22nd September  £629.37
22nd - 30th September  £1,514.12
24th - 28th September  £721.19
+73 more stays
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Greenhayes image
Greenhayes
Langton Matravers
4.8/5
Lovely, traditional cottage with stunning country views to the coast. Ideal for a romantic getaway or for small families. Pet friendly.
4
2
1
2
26th - 29th September  £603.81
26th - 30th September  £686.51
19th - 26th September  £821.80
+5 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
25th - 28th September  £725.69
19th - 29th September  £1,659.44
21st - 26th September  £988.75
+73 more stays
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IMG 5608 HDR Edit
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  £356.97
27th - 29th September  £356.97
20th - 27th September  £487.35
+7 more stays
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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
26th - 28th September  £287.50
21st - 24th September  £481.75
13th - 19th September  £953.50
+205 more stays
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3 Puddledock Cottage image
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
Enjoy soaking up the Dorset sunshine in this newly renovated countryside cottage, tucked away in the quiet village of Sutton Poyntz.
6
3
1
0
26th - 29th September  £563.96
19th - 26th September  £767.20
19th - 30th September  £1,185.60
+12 more stays
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Sea reach external
Sea Reach
Swanage
4.9/5
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime place to stay in Swanage, just 3/4 minutes’ walk from the beach.
4
2
1
0
19th - 26th September  £573.45
12th - 19th September  £628.05
12th - 26th September  £1,161.50
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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
27th - 30th September  £591.55
12th - 19th September  £973.00
5th - 19th September  £1,927.50
+12 more stays
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Garden Flat image
Garden Flat
Swanage
5/5
Gorgeous, ground floor flat in Swanage with parking and a garden.
4
2
2
0
26th - 27th September  £542.20
26th - 28th September  £610.45
20th - 30th September  £1,376.70
+11 more stays
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Capstone image
Capstone
Swanage
5/5
A beautiful Edwardian home, which is an ideal base for friends and extended family to share adventures on the South coast. Two minute flat walk from beach and town.
8
4
2
0
26th - 29th September  £664.37
27th - 28th September  £664.37
27th - 30th September  £664.37
+7 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
5th - 19th September  £1,766.85
5th - 12th September  £962.50
+2 more stays
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Dream Cottage image
Dream Cottage
Portland
5/5
One of our dream cottages a stylish, compact cottage - ideal for friends and small families to get together to enjoy the coast, walking and watersports.
6
3
2
0
29th - 30th September  £481.80
15th - 18th September  £654.37
7th - 19th September  £1,770.75
+312 more stays
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