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Osmington Vacation Rentals

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Our top choices for Osmington vacation rentals

1. Woodbine Cottage

Woodbine Cottage
2.0 star property
Weymouth
The price is CA $1,083
CA $1,299 total
includes taxes & fees
Oct 22 - Oct 23
Woodbine Cottage

2. Laurel Cottage

Laurel Cottage
3.5 star property
Weymouth
The price is CA $791
CA $950 total
includes taxes & fees
Oct 24 - Oct 25
Laurel Cottage

3. Rose Cottage

Rose Cottage
2.0 star property
Weymouth
The price is CA $1,150
CA $1,380 total
includes taxes & fees
Oct 24 - Oct 25
Rose Cottage

4. 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 $924
CA $1,109 total
includes taxes & fees
Oct 31 - Nov 1
Norden Cottage

5. Waterson

Waterson
3.0 star property
Weymouth
8.0 out of 10, Very good, (1 review)
"lovely location , inside house a little tired "
United Kingdom
Nigel
The price is CA $1,451
CA $1,741 total
includes taxes & fees
Nov 6 - Nov 7
Waterson

6. Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is CA $758
CA $909 total
includes taxes & fees
Oct 29 - Oct 30
Sea Spray

7. 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 CA $170
CA $518 total
includes taxes & fees
Oct 20 - Oct 21
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

8. 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 CA $147
CA $225 total
includes taxes & fees
Nov 1 - Nov 2
Cosy Peacehaven. Free on site Parking! Pet friendly!

9. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
The price is CA $129
CA $268 total
includes taxes & fees
Nov 9 - Nov 10
Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

10. 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 CA $183
CA $277 total
includes taxes & fees
Oct 21 - Oct 22
Private Luxury By The Sea

11. 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 CA $302
CA $343 total
includes taxes & fees
Oct 26 - Oct 27
Hardy View Farm House

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.
The price is CA $153
CA $275 total
includes taxes & fees
Oct 26 - Oct 27
Chic Modern Apartment Suite - Free Parking & WiFi!

13. 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 CA $475
CA $641 total
includes taxes & fees
Oct 26 - Oct 27
Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

14. Modern Apartment -Parking & WiFi

Modern Apartment -Parking & WiFi
Poole Old Town
9.0 out of 10, Wonderful, (8 reviews)
"Apartment was very clean and well equipped, with parking behind the building and very close to pubs, cafe and restaurant along the waterfront. "
United Kingdom
Paul
The price is CA $130
CA $253 total
includes taxes & fees
Oct 26 - Oct 27
Modern Apartment -Parking & WiFi

15. 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 $820
CA $984 total
includes taxes & fees
Oct 25 - Oct 26
Cedar Drive

16. Super Trendy Apartment - Free Parking & Fast WiFi

Super Trendy Apartment - Free Parking & Fast WiFi
Poole Old Town
10.0 out of 10, Exceptional, (1 review)
"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 CA $153
CA $275 total
includes taxes & fees
Nov 12 - Nov 13
Super Trendy Apartment - Free Parking & Fast WiFi

17. Designer Apartment inc. Free Parking & FAST WiFi

Designer Apartment inc. Free Parking & FAST WiFi
Poole Old Town
9.8 out of 10, Exceptional, (6 reviews)
"Perfect spot for our needs; well-equipped, tidy, on-site parking, and very responsive property manager. We would be happy to go back."
United States
Drew O.
The price is CA $153
CA $275 total
includes taxes & fees
Oct 26 - Oct 27
Designer Apartment inc. Free Parking & FAST WiFi

18. 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 CA $173
CA $343 total
includes taxes & fees
Oct 25 - Oct 26
Stylish modern retreat overlooking Poole Quay

19. 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 $221
CA $268 total
includes taxes & fees
Oct 21 - Oct 22
Glamping Cabin - Great for Hikers - Breakfast Inc!

20. Amazing Modern Apartment - Free Secure Parking!

Amazing Modern Apartment - Free Secure Parking!
Poole Old Town
9.6 out of 10, Exceptional, (4 reviews)
"This was a lovely apartment. It was clean and had all the essential tools for the kitchen. The laundry facilities were easy to use. It was close to shops and the harbour. Grocery store was walking distance. We enjoyed our stay in Poole."
Canada
Heidi
The price is CA $130
CA $253 total
includes taxes & fees
Oct 21 - Oct 22
Amazing Modern Apartment - Free Secure 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 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: You might want to consider this vacation home rental near Osmington, which 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?

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 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.