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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 394 Vacation Homes in Osmington with updated reviews, rates, and availability.

Stunning Waterside Cottage in Poole Harbour
Beach

Stunning Waterside Cottage in Poole Harbour

9.8 out of 10, Exceptional, (183)
"Lovely property and all equipped with everything we needed.All clean and would highly recommend."
Stunning Waterside Cottage in Poole Harbour
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Terrace/patio

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

10.0 out of 10, Exceptional, (44)
"The views are amazing. Walking path and the sea right behind house. View after view. Well equipped kitchen with tons of space, comfy living room- and I loved the sunroom out back! This was October weather with occasional rain and wind. Must be truly amazing in summer with outdoor spaces.. convenient for Dorset exploring."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Sandbanks Holiday Home Poole 5 minutes walk to the Beach Sleeps 8/9
Beach nearby, sun loungers

Sandbanks Holiday Home Poole 5 minutes walk to the Beach Sleeps 8/9

9.4 out of 10, Exceptional, (43)
"Plenty of room and a few minutes away from the beach. Would stay again. "
Sandbanks Holiday Home Poole 5 minutes walk to the Beach Sleeps 8/9
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Beach nearby

Quiet location, short walk to beach, with views of Portland and Jurassic coast

10.0 out of 10, Exceptional, (91)
"very good all round "
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Beautiful large Georgian house with a big garden. Perfect for a family or two!
Outdoor dining

Beautiful large Georgian house with a big garden. Perfect for a family or two!

10.0 out of 10, Exceptional, (69)
"We have had an amazing weekend at this beautiful property which is spacious, comfortable, quirky and full of home comforts. Everything you need is here and Wareham was a delight…we had fun in Wareham pottery painting at Pottery Corner and an amazing meal at The Italian Kitchen. Thank you so much. "
Beautiful large Georgian house with a big garden. Perfect for a family or two!
Accessible Holiday Let In Secluded Location
Outdoor dining

Accessible Holiday Let In Secluded Location

9.8 out of 10, Exceptional, (66)
"Really lovely property warm cosy and comfortable. Beds very good quality. Plenty of secure parking, lovely garden. We would highly recommend. Ideally need a car to visit local areas but only short journeys. Would have liked a local pub for evening out or a meal unfortunately the closest was about 1 mile but it’s closed down, this issue didn’t matter as we had a fabulous time and saw friends that we haven’t seen since before COVID so it was very special. Thanks to Becky for the easy communication...
Accessible Holiday Let In Secluded Location
A contemporary house close to the town centre with fantastic views over Radipole Lake.
Exterior

A contemporary house close to the town centre with fantastic views over Radipole Lake.

9.4 out of 10, Exceptional, (15)
"Good comfortable house conveniently situated close to town, beach and all local facilities. "
A contemporary house close to the town centre with fantastic views over Radipole Lake.
Refurbished house, close to the beach, quiet central location
Fridge, microwave, oven, stovetop

Refurbished house, close to the beach, quiet central location

10.0 out of 10, Exceptional, (95)
"Good place to stay , clean , near all facilities. "
Refurbished house, close to the beach, quiet central location
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Beach

Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

9.4 out of 10, Exceptional, (63)
"The cottage was as described. It had everything you could ever need. Beds were very comfortable. The view from the cottage was fantastic!! "
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Private Luxury By The Sea
Outdoor spa tub

Private Luxury By The Sea

10.0 out of 10, Exceptional, (1)
"Lovely, well equipped place to stay. Modern finish, clean and everything you need. Lovely beach a short walk away. Great communication from host"
The price is AED 563
AED 760 total
includes taxes & fees
7 May - 8 May
Private Luxury By The Sea
Brand New 4 Bedroom House -Sleeps 9 - Free Parking
Cookware/dishes/utensils, spices

Brand New 4 Bedroom House -Sleeps 9 - Free Parking

10.0 out of 10, Exceptional, (4)
"Very clean, very easy check in, communication etc. great stay, would recommend and stay again "
The price is AED 1,629
AED 2,147 total
includes taxes & fees
26 May - 27 May
Brand New 4 Bedroom House -Sleeps 9 - Free Parking
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Property grounds

Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

9.8 out of 10, Exceptional, (53)
"What a lovely, clean, well equipped, nostalgic place to stay. Nice big garden, sunny patio area, & so peaceful. Plenty of lovely walks surrounding the property. Just what my friend & I needed. Great hosts, very welcoming & helpful. Already planning our next visit! Thank you. "
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Barn conversion, quiet location and heated swimming pool ( from mid May)
Exterior

Barn conversion, quiet location and heated swimming pool ( from mid May)

9.4 out of 10, Exceptional, (59)
"Fantastic property. Great location. Clean, with all the necessary facilities and utilities."
Barn conversion, quiet location and heated swimming pool ( from mid May)
Stable Conversion Near Lulworth Cove/Jurassic Coast
Beach nearby, sun loungers

Stable Conversion Near Lulworth Cove/Jurassic Coast

10.0 out of 10, Exceptional, (106)
"We had a lovely time on our stay in this cosy and beautifully clean property all was as described, and the milk, tea and cookies were a lovely touch. The booking in process was really easy and Paul was a good host. The garden is nicely kept and a paradise if you like birdwatching and the beautiful local surrounding area makes this a wonderful place to stay. We would definately recommend"
Stable Conversion Near Lulworth Cove/Jurassic Coast
Holly Cottage - Two Bedroom House, Sleeps 4
Exterior

Holly Cottage - Two Bedroom House, Sleeps 4

10.0 out of 10, Exceptional, (1)
"Very good"
The price is AED 2,468
AED 2,468 total
includes taxes & fees
8 May - 9 May
Holly Cottage - Two Bedroom House, Sleeps 4
OUR LOVELY HOME WITH KITCHEN BALCONY WITH VIEWS OVER SWANAGE BAY/PURBECK HILLS
Beach nearby

OUR LOVELY HOME WITH KITCHEN BALCONY WITH VIEWS OVER SWANAGE BAY/PURBECK HILLS

9.8 out of 10, Exceptional, (34)
"Lovely house with lots of space for all the family "
OUR LOVELY HOME WITH KITCHEN BALCONY WITH VIEWS OVER SWANAGE BAY/PURBECK HILLS
Host & Stay | Clearmount Cottage
Outdoor dining

Host & Stay | Clearmount Cottage

10.0 out of 10, Exceptional, (3)
"What a beautiful property tucked away in a fantastic location. The gardens were equally as enjoyable as the house and we were lucky with the sunshine.Great access to Castle Cove beach, Sandsfoot Castle gardens, and the Rodwell Trail, all within a 5 minute walk.Thank you, we will definitely be back."
Host & Stay | Clearmount Cottage
Kings Cottage - Swanage
Fridge, microwave, oven, dishwasher

Kings Cottage - Swanage

The price is AED 3,304
AED 3,304 total
includes taxes & fees
10 May - 11 May
Kings Cottage - Swanage
Historical, Characterful, Converted Old School House
Exterior

Historical, Characterful, Converted Old School House

9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
Historical, Characterful, Converted Old School House
Bay View 2 Bed Lodge with Sea Views Poole Harbour Sleeps 4
Stovetop, freezer

Bay View 2 Bed Lodge with Sea Views Poole Harbour Sleeps 4

10.0 out of 10, Exceptional, (1)
"A great weekend in this immaculate and extremely modern caravan with outstanding sea views. Excellent communication with the host throughout the entire booking process. Would highly recommend."
Bay View 2 Bed Lodge with Sea Views Poole Harbour Sleeps 4
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Osmington

The Dorset Resort
Signature Chalet, 3 Bedrooms, Accessible, Sauna | Desk, laptop workspace, blackout drapes, iron/ironing board

The Dorset Resort

4.0 star property
10.0 out of 10, Exceptional, (29)
"The property was clean. Just the beds were single Beds in all couple rooms. Would be great if they had double beds instead. "
The Dorset Resort
Stunning Waterside Cottage in Poole Harbour
Beach

Stunning Waterside Cottage in Poole Harbour

9.8 out of 10, Exceptional, (183)
"Lovely property and all equipped with everything we needed.All clean and would highly recommend."
Stunning Waterside Cottage in Poole Harbour
Herston Caravan & Campsite
BBQ/picnic area

Herston Caravan & Campsite

2.0 star property
8.2 out of 10, Very Good, (24)
"Not bad site we was out of season so a big bonus tents close to get but only ones there so not a problem toilets showers clean modern new and allocation to one person only which was great"
Herston Caravan & Campsite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.