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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

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
27th - 30th September 2025  £635.35
28th - 29th September 2025  £635.35
27th - 29th September 2025  £635.35
+7 more stays
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holiday home wareham with hot tub
Cherry Lodge
Wareham
4.7/5
Comfort and space to be enjoyed by friends and family in this large, modern home complete with bubbling hot tub. Its pet friendly and has plenty of parking. The quality of this home and the size of the garden are what attracts guests to Cherry Lodge.
9
4
2
2
19th - 26th September 2025  £1,245.00
5th - 19th September 2025  £2,870.00
12th - 26th September 2025  £2,620.00
+2 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 2025  £659.05
5th - 12th September 2025  £767.20
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Canaan image
Canaan
Worth Matravers
4.9/5
4 bedrooms. A wonderful architecturally designed, large family holiday home in Worth Matravers. Completed to the highest standard and incorporating a sumptuous interior. It’s open plan design, galleried first floor landing and very large kitchen makes this the ideal choice for the extended family, walkers and those of you who wish to relax in this stylish property set in the heart of the English coastal countryside.
8
4
3
2
20th - 27th September 2025  £1,146.25
6th - 20th September 2025  £2,782.20
6th - 13th September 2025  £1,491.70
+2 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
28th - 29th September 2025  £481.80
5th - 13th September 2025  £1,486.74
14th - 25th September 2025  £1,513.20
+312 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
26th - 29th September 2025  £619.14
26th - 28th September 2025  £619.14
+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
27th - 30th September 2025  £858.00
19th - 27th September 2025  £2,173.00
26th - 27th September 2025  £858.00
+16 more stays
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The Bungalow
Little Westport
Wareham
4.8/5
Little Westport is a charming 1960s four-bedroom Colt House, in a peaceful setting with a large garden overlooking the Purbeck Hills. A perfect location for a break to enjoy walking, cycling or exploring the area.
8
4
2
0
19th - 26th September 2025  £734.65
12th - 19th September 2025  £995.05
12th - 26th September 2025  £1,679.70
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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 2025  £629.37
21st - 23rd September 2025  £629.37
20th - 27th September 2025  £904.75
+73 more stays
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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
20th - 27th September 2025  £724.15
13th - 27th September 2025  £1,398.30
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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
24th - 27th September 2025  £675.86
22nd - 24th September 2025  £675.86
14th - 16th September 2025  £775.51
+22 more stays
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Piona Flat 12 The Gables Ph3 Web
Piona
Swanage
4.9/5
For a seaside break to remember, look no further! Piona is set in a prime location in the heart of Swanage in Dorset. You will have a wealth of attractions, amenities and the all-important sandy beach right at your fingertips – all just a 5 minute walk away!
6
3
2
0
20th - 27th September 2025  £653.80
6th - 13th September 2025  £784.00
13th - 27th September 2025  £1,317.45
+2 more stays
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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 2025  £1,016.05
5th - 19th September 2025  £2,166.90
12th - 19th September 2025  £1,070.65
+2 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
24th - 27th September 2025  £372.30
13th - 23rd September 2025  £759.85
13th - 27th September 2025  £1,016.05
+52 more stays
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IMG 1708 HDR Edit
The Lawns
Charlton Marshall, Nr Blandford
4.8/5
2 bedroom holiday cottage near to Blandford in the pretty village of Charlton Marshall, lovely country views and walks. Property all on one level with stunning garden.
4
2
1
2
6th - 13th September 2025  £681.10
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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
22nd - 25th September 2025  £485.01
13th - 25th September 2025  £1,137.60
6th - 13th September 2025  £897.40
+16 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 - 20th September 2025  £1,243.90
13th - 27th September 2025  £2,275.05
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The Aspens image
The Aspens
Swanage
4.8/5
Delightful light-filled family holiday home, situated just a stone’s throw from beautiful Swanage Pier.
5
2
2
0
27th - 30th September 2025  £469.68
19th - 26th September 2025  £638.05
26th - 30th September 2025  £532.16
+10 more stays
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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
20th - 27th September 2025  £746.20
6th - 13th September 2025  £924.70
13th - 20th September 2025  £924.70
+7 more stays
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Froxfield Cottage image
Froxfield Cottage
Langton Matravers
4.9/5
3 Bedrooms. Froxfield Cottage is a cosy renovated quarryman’s cottage built in the 1850’s, sympathetically decorated in a mix of contemporary and traditional style.
6
3
2
1
26th - 29th September 2025  £606.88
19th - 26th September 2025  £826.00
26th - 28th September 2025  £606.88
+9 more stays
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