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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

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
22nd - 25th September 2025  £485.01
6th - 13th September 2025  £897.40
13th - 25th September 2025  £1,137.60
+16 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 2025  £619.14
27th - 29th September 2025  £619.14
5th - 12th September 2025  £842.80
+4 more stays
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Littlecot image
Littlecot
Weymouth
5/5
A gorgeous, detached family home within stones throw of Smallmouth Bay and the Rodwell trail. Ideal for those who want a comfy base for friends or extended family.
8
4
2
2
26th - 29th September 2025  £858.00
26th - 28th September 2025  £858.00
27th - 28th September 2025  £858.00
+16 more stays
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Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.5/5
Located in the sought-after National Trust-owned village of Corfe Castle, Ridgeview Cottage is a modern, detached, family home found moments away from many of Dorset’s prolific attractions.
6
3
2
0
22nd - 25th September 2025  £675.86
15th - 19th September 2025  £884.08
17th - 19th September 2025  £775.51
+22 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 2025  £1,091.65
5th - 19th September 2025  £2,133.30
12th - 26th September 2025  £2,133.30
+2 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 2025  £840.66
19th - 27th September 2025  £1,320.00
27th - 29th September 2025  £840.66
+12 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
26th - 29th September 2025  £366.97
13th - 27th September 2025  £982.50
26th - 30th September 2025  £413.97
+12 more stays
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Angel Cottage
Angel Cottage
Swanage
4.7/5
Nothing is more refreshing than a coastal holiday near the sea and if you’re looking for a cosy, quaint cottage, Angel Cottage should be first on your wishlist. This mid terrace cottage is the perfect base to discover miles of heritage coastline or relax and unwind on the blue flag sandy beach
2
1
1
2
25th - 28th September 2025  £372.30
23rd - 29th September 2025  £508.35
22nd - 28th September 2025  £508.35
+52 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
12th - 19th September 2025  £854.35
5th - 12th September 2025  £962.50
19th - 26th September 2025  £854.35
+2 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
27th - 30th September 2025  £629.37
23rd - 24th September 2025  £629.37
23rd - 28th September 2025  £904.75
+73 more stays
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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
27th - 28th September 2025  £481.80
12th - 22nd September 2025  £1,450.46
13th - 18th September 2025  £894.75
+312 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 holiday hotspot, just 3/4 minutes’ walk from the beach.
4
2
1
0
19th - 26th September 2025  £583.45
12th - 26th September 2025  £1,171.50
5th - 12th September 2025  £691.60
+2 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
28th - 30th September 2025  £673.75
10th - 21st September 2025  £1,645.00
11th - 17th September 2025  £1,065.00
+198 more stays
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27 West Street Ph17 Web
The Old Butcher’s Cottage
Corfe Castle
4.9/5
The Old Butcher’s Cottage is bursting with character. Recently renovated throughout, this high spec property is the hideaway you’ve been searching for. Luxurious furnishings and exquisite linens adorn the bedrooms, living area and kitchen, providing stunning accommodation that the whole family will remember. Parties of all kinds can enjoy home cooked meals in the large open plan kitchen-lounge area and gather around the dining table for drinks or a board game.
6
3
2
2
20th - 27th September 2025  £1,081.15
13th - 27th September 2025  £2,275.05
13th - 20th September 2025  £1,243.90
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IMG 7696
Daisy’s
Swanage
4.7/5
Stylishly decorated 3 bedroom holiday home in Swanage. Daisy's offers everything you need for a relaxing break, from comfortable bedrooms with ensuite for each room to a private bubbling hot tub, perfect for unwinding after a long day exploring the coast!
6
3
3
1
26th - 29th September 2025  £645.97
27th - 28th September 2025  £645.97
20th - 30th September 2025  £1,246.50
+16 more stays
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Leap House image
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
19th - 26th September 2025  £734.65
12th - 26th September 2025  £1,419.30
12th - 19th September 2025  £734.65
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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
13th - 20th September 2025  £724.15
13th - 27th September 2025  £1,398.30
20th - 27th September 2025  £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 2025  £1,141.00
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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 2025  £632.50
28th - 30th September 2025  £632.50
27th - 29th September 2025  £632.50
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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
26th - 29th September 2025  £591.55
27th - 29th September 2025  £591.55
19th - 28th September 2025  £1,035.00
+12 more stays
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