A coastal landscape with a rocky shoreline and calm sea under a clear sky.

Osmington Vacation Rentals

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Our top choices for Osmington vacation rentals

1. Bracken Cottage

Bracken Cottage
3.0 star property
Weymouth
8.0 out of 10, Very good, (1 review)
"Had a great 6 night stay here. Check in was very easy, key safe on the wall outside. As soon as we got inside the cottage, which had a lovely warm welcoming cosy feel to it. We loved all the little extra decorations scattered around. Well stocked with plates, glasses cutlery etc.. Even some extras that we didn't expect like the smoothie blender and spice rack. Only downside was all the towels were bundled in a heap on the bathroom floor. Not sure what had happened here, whether the cleaners had...
United Kingdom
michael
The price is CA $732
CA $879 total
includes taxes & fees
Sep 12 - Sep 13
Bracken Cottage

2. Rose Cottage

Rose Cottage
2.0 star property
Weymouth
The price is CA $1,139
CA $1,367 total
includes taxes & fees
Sep 15 - Sep 16
Rose Cottage

3. Woodbine Cottage

Woodbine Cottage
2.0 star property
Weymouth
The price is CA $1,073
CA $1,287 total
includes taxes & fees
Sep 21 - Sep 22
Woodbine Cottage

4. Laurel Cottage

Laurel Cottage
3.5 star property
Weymouth
The price is CA $784
CA $941 total
includes taxes & fees
Sep 8 - Sep 9
Laurel Cottage

5. Norden Cottage

Norden Cottage
3.0 star property
Weymouth
6.0 out of 10, (1 review)
"The cottage itself is lovely, and has a lot of potential. It’s a large cottage which accomodates 5. Lighting wasn’t working in all rooms which was a nuisance and the facilities in the kitchen were dirty and not maintained well. Oven and stove worked, coffee machine filthy. Given that you would hire a cottage to do self catering, it wasn’t one of the better cottages we have stayed in. We found it a cold welcoming, no welcome note, only a small box of biscuits on entry. Cottage was really...
United Kingdom
Hilary
The price is CA $916
CA $1,099 total
includes taxes & fees
Oct 3 - Oct 4
Norden Cottage

6. Cedar Drive

Cedar Drive
2.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"So clean I could roll around in the property, also very thoughtful of the host, even a fly squatter was available. Would highly recommend if you’re in the area."
United Kingdom
David
The price is CA $812
CA $975 total
includes taxes & fees
Oct 4 - Oct 5
Cedar Drive

7. Glamping Cabin - Great for Hikers - Breakfast Inc!

Glamping Cabin - Great for Hikers - Breakfast Inc!
3.0 star property
Swanage
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and ideal for travellers with pets . Great location , walking distance to the coastal path and very close drives to National Trust areas such as Corfe Castle and Studland beaches"
United Kingdom
Vanessa
The price is CA $241
CA $288 total
includes taxes & fees
Sep 6 - Sep 7
Glamping Cabin - Great for Hikers - Breakfast Inc!

8. Brewery View

Brewery View
2.0 star property
Rodwell
10.0 out of 10, Exceptional, (1 review)
"Very clean, location great, comfortable and we received regular updates and communication. All very helpful"
United Kingdom
Helen
The price is CA $717
CA $861 total
includes taxes & fees
Sep 11 - Sep 12
Brewery View

9. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is CA $963
CA $1,156 total
includes taxes & fees
Sep 13 - Sep 14
Manhattan Beach

10. Jay Cottage

Jay Cottage
3.5 star property
Wyke Regis
The price is CA $586
CA $703 total
includes taxes & fees
Oct 1 - Oct 2
Jay Cottage

11. Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is CA $755
CA $906 total
includes taxes & fees
Oct 2 - Oct 3
Sea Spray

12. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is CA $890
CA $1,068 total
includes taxes & fees
Sep 20 - Sep 21
Bear's Apartment

13. Wey Cottage

Wey Cottage
3.5 star property
Rodwell
The price is CA $712
CA $855 total
includes taxes & fees
Oct 3 - Oct 4
Wey Cottage

14. Admiral's Quarter Apartment 5

Admiral's Quarter Apartment 5
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Ideally placed to have a stroll to the harbour with the convenience of secure parking within the gated community. Within easy reach of pubs/restaurants (try the burgers at the Northe tavern 100 yards away) but a quiet area. It's in a residential block, most of residents friendly but there are rules on no ball games or storing of fishing rods/beach equipment outside of apartment to keep area clear. Designated space for car, big enough for my range rover, even though 1 neighbour came and checked...
United Kingdom
Richard
The price is CA $732
CA $878 total
includes taxes & fees
Sep 17 - Sep 18
Admiral's Quarter Apartment 5

15. Coastguard Lookout

Coastguard Lookout
2.0 star property
Wyke Regis
The price is CA $711
CA $853 total
includes taxes & fees
Sep 13 - Sep 14
Coastguard Lookout

16. Bliss On The Bay

Bliss On The Bay
3.5 star property
Weymouth Town Center
The price is CA $1,003
CA $1,203 total
includes taxes & fees
Sep 21 - Sep 22
Bliss On The Bay

17. 26 High West

26 High West
3.0 star property
Rodwell
8.8 out of 10, Excellent, (3 reviews)
"Property was in a good location with pay to park nearby. Property was well maintained but things such as blinds and lamp in bedroom need a bit of tlc"
United Kingdom
Richard
The price is CA $630
CA $756 total
includes taxes & fees
Oct 1 - Oct 2
26 High West

18. Flat 6, Thornlow Heights

Flat 6, Thornlow Heights
3.0 star property
Southlands
The price is CA $781
CA $937 total
includes taxes & fees
Sep 14 - Sep 15
Flat 6, Thornlow Heights

19. Groves House

Groves House
3.0 star property
Portland
The price is CA $736
CA $884 total
includes taxes & fees
Sep 10 - Sep 11
Groves House

20. Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (2 reviews)
"It was in a peaceful location, although a bit far for walking into town. But the facilities were spot on, though there is no oven to cook proper meals. For someone who needs a quiet, chilled out, restful timeout, it is the perfect place to stay."
United Kingdom
Kim
The price is CA $646
CA $775 total
includes taxes & fees
Sep 9 - Sep 10
Hide-a-way
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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Top Osmington Hotel Reviews

Find out more about Osmington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osmington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Osmington?

Yes, there are vacation rentals near popular attractions in Osmington, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Osmington?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: Visitors like this Osmington vacation home rental. It comes with WiFi so you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Osmington?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Osmington stay.

What can I see and do in Osmington?

Osmington Bay Beach and Weymouth Bay are a couple of lovely local spots to get outside and enjoy nature. While here, Dorset and East Devon Coast and Ringstead Beach are other places worth a visit.

What are vacation rentals like in Osmington?

Vacation rentals are privately owned properties you can book for a couple days or more in Osmington. Vacation rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.