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Osmington Holiday Rentals

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Our top choices for Osmington holiday rentals

1. 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 NZ$1,557
includes taxes & fees
13 Nov - 14 Nov
Norden Cottage

2. Laurel Cottage

Laurel Cottage
3.5 star property
Weymouth
The price is NZ$1,333
includes taxes & fees
13 Nov - 14 Nov
Laurel Cottage

3. Woodbine Cottage

Woodbine Cottage
3.0 star property
Weymouth
The price is NZ$1,781
includes taxes & fees
14 Nov - 15 Nov
Woodbine Cottage

4. Cedar Drive

Cedar Drive
3.0 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 NZ$1,381
includes taxes & fees
12 Nov - 13 Nov
Cedar Drive

5. Cosy Peacehaven. Free on site Parking! Pet friendly!

Cosy Peacehaven. Free on site Parking! Pet friendly!
Weymouth Town Center
9.4 out of 10, Exceptional, (3 reviews)
"Perfect flat which contained everything we needed for a great stay. It is in an excellent location and parking was a great bonus to us. Communication was great with clear instructions and thoughtful little extras."
United Kingdom
Chloe
The price is NZ$264
includes taxes & fees
10 Nov - 11 Nov
Cosy Peacehaven. Free on site Parking! Pet friendly!

6. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (5 reviews)
"The house was outstanding, probably the best we’ve ever experienced. It is exceptionally clean, comfortable for our family of 5, and convenient to the sites in the area. We would stay there again if we return."
United States
Kristina
The price is NZ$612
includes taxes & fees
11 Nov - 12 Nov
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

7. Private Luxury By The Sea

Private Luxury By The Sea
Poole
9.6 out of 10, Exceptional, (8 reviews)
"Nice location, quiet and relaxing"
United Kingdom
Luke
The price is NZ$342
includes taxes & fees
10 Nov - 11 Nov
Private Luxury By The Sea

8. 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 NZ$378
includes taxes & fees
10 Nov - 11 Nov
Glamping Cabin - Great for Hikers - Breakfast Inc!

9. Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is NZ$414
includes taxes & fees
12 Nov - 13 Nov
Hardy View Farm House

10. Elegant Apartment inc. Parking

Elegant Apartment inc. Parking
Poole Old Town
9.6 out of 10, Exceptional, (5 reviews)
"Very impressed with the very professional set-up of the apartments, clean, comfortable and extremely well equipped. Great location near lots of good places to eat. Can’t fault our stay! We will definitely re-book for another stay in Poole."
United States
Peter L.
The price is NZ$296
includes taxes & fees
12 Nov - 13 Nov
Elegant Apartment inc. Parking

11. Modern Apartment -Parking & WiFi

Modern Apartment -Parking & WiFi
Poole Old Town
9.0 out of 10, Wonderful, (8 reviews)
"Great place well be presented very clean"
United States
Jo R.
The price is NZ$296
includes taxes & fees
15 Nov - 16 Nov
Modern Apartment -Parking & WiFi

12. Chic Modern Apartment Suite - Free Parking & WiFi!

Chic Modern Apartment Suite - Free Parking & WiFi!
Poole Old Town
10.0 out of 10, Exceptional, (5 reviews)
"The apartment was very clean and comfortable. It is stylishly furnished and extremely centrally located. The secure parking, in such a central location as a real plus. It is literally moments on foot from the quay. We would not hesitate to stay here again."
United States
Richard W.
Chic Modern Apartment Suite - Free Parking & WiFi!

13. Super Trendy Apartment - Free Parking & Fast WiFi

Super Trendy Apartment - Free Parking & Fast WiFi
Poole Old Town
10.0 out of 10, Exceptional, (2 reviews)
"Small, clean apartment, very handy for the harbour and old town. Well equipped. Not the best view from the balcony but can't have everything. Good communication from the host. First time on vrbo and can't fault them"
United States
Tim H.
The price is NZ$296
includes taxes & fees
12 Nov - 13 Nov
Super Trendy Apartment - Free Parking & Fast WiFi

14. Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is NZ$1,276
includes taxes & fees
12 Nov - 13 Nov
Sea Spray

15. 1 bedroom accommodation in Ibberton, Blandford Forum

1 bedroom accommodation in Ibberton, Blandford Forum
Ibberton, Blandford Forum
10.0 out of 10, Exceptional, (12 reviews)
"Lovely place, lovely countryside."
United States
Paul Mitchell
The price is NZ$330
includes taxes & fees
12 Nov - 13 Nov
1 bedroom accommodation in Ibberton, Blandford Forum

16. Stylish modern retreat overlooking Poole Quay

Stylish modern retreat overlooking Poole Quay
Poole
10.0 out of 10, Exceptional, (2 reviews)
"Nice Place, would stay again!"
United Kingdom
David R.
The price is NZ$397
includes taxes & fees
10 Nov - 11 Nov
Stylish modern retreat overlooking Poole Quay

17. Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

Classic Yacht Nadine with Hot Tub, Poole Harbour Bay
Poole
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely amazing stay! Wish it was for longer! The boat could have had some extra TLC but otherwise we will definitely return!"
United States
Lesley-Anne W.
The price is NZ$761
includes taxes & fees
10 Nov - 11 Nov
Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

18. Beautiful Couples Retreat - FREE Parking & WiFi

Beautiful Couples Retreat - FREE Parking & WiFi
Poole Old Town
10.0 out of 10, Exceptional, (6 reviews)
"Lovely clean flat in the PERFECT location in Poole, very easily accessible and great communication with host throughout. Would recommend - 5* "
United Kingdom
Frazer
The price is NZ$296
includes taxes & fees
11 Nov - 12 Nov
Beautiful Couples Retreat - FREE Parking & WiFi

19. Bluebell Wood

Bluebell Wood
Harman's Cross
10.0 out of 10, Exceptional, (1 review)
"A wonderful stay in a quaint, beautiful cosy cabin. The location was very tranquil, surrounded by nature and the host has put a lot of time into making these cabins feel like home. I look forward to visiting again"
United Kingdom
Liam
The price is NZ$441
includes taxes & fees
10 Nov - 11 Nov
Bluebell Wood

20. Beautiful NEW 3 bedroom house - garden & parking

Beautiful NEW 3 bedroom house - garden & parking
Poole
10.0 out of 10, Exceptional, (15 reviews)
"Amazing place "
United Kingdom
Lee
The price is NZ$407
includes taxes & fees
12 Nov - 13 Nov
Beautiful NEW 3 bedroom house - garden & parking
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osmington holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osmington. 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 Osmington. 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 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 holiday 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 Osmington short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Osmington?

Yes, there are holiday rentals close to the most popular sights in Osmington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osmington has to offer?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This holiday home rental outside of Osmington comes with WiFi so that you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Osmington?

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

What can I see and do in Osmington?

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

What are holiday rentals like in Osmington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osmington. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.