beautiful dorset landscape to be enjoyed on a dorset holiday
Discover

What's on in Dorset in September 2025

Keep up to date with Dorset

SUBSCRIBE TO OUR NEWSLETTER

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!

Find a September

Holiday Cottage in Dorset

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
View & Book
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
22nd - 27th September  £988.75
20th - 21st September  £725.69
+73 more stays
View & Book
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
26th - 27th September  £481.80
23rd - 26th September  £600.71
19th - 26th September  £821.25
+312 more stays
View & Book
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
27th - 30th September  £563.96
26th - 30th September  £640.65
19th - 26th September  £767.20
+12 more stays
View & Book
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  £854.35
12th - 26th September  £1,658.70
5th - 12th September  £962.50
+2 more stays
View & Book
Castle View House
Corfe Castle
5/5
Escape the ordinary at Castle View House, a haven in the countryside that accommodates up to nine guests. With its enchanting views of Corfe Castle, stylish open-plan interiors, and dog-friendly atmosphere, this residence promises a unique and memorable retreat. Nestled in the heart of Corfe Castle village, it provides an ideal setting for switching off from the demands of everyday life and savoring every moment with friends and family. Whether you're captivated by the historic charm of the surroundings or indulging in the comfort of the stylish interiors, Castle View House invites you to create lasting memories in a tranquil and welcoming escape.
9
5
4
1
19th - 26th September  £1,645.00
5th - 12th September  £2,479.75
View & Book
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  £645.97
28th - 30th September  £645.97
27th - 28th September  £645.97
+12 more stays
View & Book
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  £1,303.75
5th - 12th September  £1,566.25
12th - 26th September  £2,747.50
+2 more stays
View & Book
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
20th - 25th September  £904.75
12th - 21st September  £1,650.62
+73 more stays
View & Book
Garden Flat
Swanage
5/5
Gorgeous, ground floor flat in Swanage with parking and a garden.
4
2
2
0
28th - 29th September  £542.20
27th - 29th September  £610.45
26th - 28th September  £610.45
+11 more stays
View & Book
Beach Approach
Swanage
4.7/5
Settle into a lovely family holiday at Beach Approach. A two bedroom ground floor apartment. A flat walk will take you to Swanage beach and High Street, which is lined with cute cafés, boutiques, and fine restaurants. Beach Approach is perfect for families with top sights in easy reach: Swanage Railway is just a two minute stroll away; take a trip down memory lane on the vintage steam engine to the historic village of Corfe Castle.
4
2
1
0
27th - 30th September  £481.17
28th - 30th September  £481.17
20th - 28th September  £757.20
+6 more stays
View & Book
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  £724.15
13th - 27th September  £1,398.30
20th - 27th September  £724.15
View & Book
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
13th - 20th September  £1,340.50
6th - 20th September  £2,782.20
6th - 13th September  £1,491.70
View & Book
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  £366.97
26th - 30th September  £413.97
20th - 29th September  £639.45
+7 more stays
View & Book
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
22nd - 25th September  £372.30
22nd - 30th September  £582.40
13th - 27th September  £1,016.05
+52 more stays
View & Book
Cricket Cottage
Swanage
4.7/5
This quaint seaside cottage is the perfect destination for two to enjoy a romantic getaway in the heart of Swanage. Just a 20-minute meander from the main beach, sparkling clear Swanage shores, shops, restaurants and attractions. Space is plentiful in this deceptively generous cottage.
2
1
1
0
13th - 20th September  £465.30
20th - 30th September  £649.00
6th - 20th September  £956.20
+5 more stays
View & Book
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
27th - 30th September  £469.68
19th - 26th September  £638.05
12th - 19th September  £638.05
+12 more stays
View & Book
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
5th - 12th September  £1,146.25
12th - 26th September  £2,036.70
+2 more stays
View & Book
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  £1,081.15
13th - 27th September  £2,275.05
13th - 20th September  £1,243.90
View & Book
Little Westport
Wareham
4.8/5
Little Westport is a charming large cottage in Wareham with four-bedroom. This former Colt House, is in a peaceful setting with a large garden overlooking the Purbeck Hills.
8
4
2
0
19th - 26th September  £734.65
View & Book