Osmington Holiday Rentals from AU$277: Search Short-Term Rentals

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Our top choices for Osmington holiday rentals

A kitchen with white cabinets, a tiled floor, and a window.

1. Rose Cottage

Weymouth

includes taxes & fees

28 Sept - 29 Sept

A hotel room with two beds, a bedside table with a lamp, a small bedside table with a mirror, and a wall-mounted picture.

2. Woodbine Cottage

Weymouth

includes taxes & fees

21 Sept - 22 Sept

A rustic stone cottage with a thatched roof, a wooden deck, and a round metal table set with cups and pastries.

3. Laurel Cottage

Weymouth

includes taxes & fees

9 Oct - 10 Oct

A cozy room with a stone wall, a fireplace, a sofa, and a window.

4. Norden Cottage

Weymouth

"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...

Hilary

includes taxes & fees

26 Sept - 27 Sept

A room with large windows offering a view of a coastal landscape.

5. Waterson

Weymouth

Nigel

includes taxes & fees

10 Oct - 11 Oct

A beach with people, a large striped tower, and buildings in the background.

6. The Sailors Studio|Sleeps2|Weymouth Beach|

Weymouth Town Center

includes taxes & fees

15 Sept - 16 Sept

A beach with a natural rock arch formation.

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

Wool

Kristina

includes taxes & fees

15 Sept - 16 Sept

A residential property with a patio, a sliding glass door, and a brick exterior.

8. Cedar Drive

Weymouth

David

includes taxes & fees

3 Oct - 4 Oct

9. Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage

Harman's Cross

includes taxes & fees

16 Sept - 17 Sept

A bathroom with a window, a sink, and two potted plants.

10. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

21 Sept - 22 Sept

A wooden exterior with a sliding glass door, a small window, and a potted plant.

11. The Perk Inn, Cosy & Secluded Garden Lodge

Poole

includes taxes & fees

6 Oct - 7 Oct

A modern outdoor patio with wicker furniture and a glass door leading to a covered area.

12. Private Luxury By The Sea

Poole

Richard

includes taxes & fees

4 Oct - 5 Oct

A modern living room with a grey sofa, yellow cushions, a yellow rug, and a large window with curtains.

13. Brand NEW 3 bedroom house - garden & parking +wifi

Poole

James

includes taxes & fees

20 Sept - 21 Sept

A neatly made bed with two towels folded into robes, a pillow, and a small card on the bed.

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

Swanage

Vanessa

includes taxes & fees

17 Sept - 18 Sept

A modern living room with a brick wall, a dining area with a table and chairs, and a sofa.

15. Modern Apartment -Parking & WiFi

Poole Old Town

Paul

includes taxes & fees

20 Sept - 21 Sept

A hotel room with a bed, green sofa, and a glass coffee table with a vase of flowers.

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

Poole Old Town

Richard W.

includes taxes & fees

21 Sept - 22 Sept

A modern living room with a sofa, a round table, and a television mounted on the wall.

17. Elegant Apartment inc. Parking

Poole Old Town

Peter L.

includes taxes & fees

1 Oct - 2 Oct

A waterfront with several boats docked, a row of buildings with various businesses, and a clear sky.

18. Day Cottage

Weymouth Town Center

Cindy

includes taxes & fees

28 Sept - 29 Sept

A modern hotel room with a bed, a black tray with pastries, a window with a view, and a wall-mounted shelf with a plant.

19. Stylish modern retreat overlooking Poole Quay

Poole

David R.

includes taxes & fees

15 Sept - 16 Sept

A living room with a wooden floor, a brown leather sofa, a wooden coffee table, a TV mounted on the wall, and large windows with curtains.

20. Designer Apartment inc. Free Parking & FAST WiFi

Poole Old Town

Drew O.

includes taxes & fees

20 Sept - 21 Sept

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Top Osmington Hotel Reviews

Holiday Inn Express Poole by IHG

8/10 Good

"very well presented and the staff were very pleasant. we thought the car park was over priced as we only stayed one night. Premeir Inn only charge £3.00."

Sandbanks Hotel

8/10 Good

"We enjoyed our long weekend at the Sand Banks Hotel. Our room had a beautiful view. We enjoyed the breakfasts & spent many a happy hour in the outside seating area with the wider family. The staff throughout the hotel were friendly & very helpful. The chambermaids kept the room well, topping up with essentials. We will certainly go again."

Fairhaven Hotel

8/10 Good

"A pleasant family-run establishment that gave a warm and helpful welcome. Very efficient room servicing, not replacing towels or mats unnecessarily - a contribution to poluution reduction, but no notice stating policy. One or two annoying little faults: TV had a weak signal and the screen broke up rather often, soap etc. dispensers didn't dispense without a lot of effort, drawers opened and wouldn't close again."

The Knoll House

8/10 Good

"A lovely but tired classic old fashioned hotel. We stayed in the garden wing. Functional but snug bedroom. The bathroom and loo had been upgraded and were pretty decent. The hot water for the somewhat weak shower was very limited and so cool was the order of the day! Loved having a separate loo. Dinner was fab. Tasty and great value. Breakfast too was super! Cannot fault the staff. Friendly and helpful. All in all it’s a lovely old fashioned hotel with a great comfortable feel."

The Jubilee Hotel East- with Spa Facilities

10/10 Excellent

"The room was clean, staff were helpful, breakfast was a buffet style so you could eat as much or as little as you want, the bar staff were friendly and helpful, all the food was cooked well and hot, they accomadte for disabilities and are dog friendly for well behaved dogs"

Find out more about Osmington

Everything you need to know about Osmington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osmington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osmington holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Osmington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osmington. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osmington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osmington holiday rentals we have selected for you start as low as AU$277 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osmington rentals

At Expedia, we put the best Osmington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osmington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osmington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osmington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Check prices for these dates

Our top choices for Osmington holiday rentals

1. Rose Cottage

2. Woodbine Cottage

3. Laurel Cottage

4. Norden Cottage

5. Waterson

6. The Sailors Studio|Sleeps2|Weymouth Beach|

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

8. Cedar Drive

9. Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage

10. Hardy View Farm House

11. The Perk Inn, Cosy & Secluded Garden Lodge

12. Private Luxury By The Sea

13. Brand NEW 3 bedroom house - garden & parking +wifi

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

15. Modern Apartment -Parking & WiFi

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

17. Elegant Apartment inc. Parking

18. Day Cottage

19. Stylish modern retreat overlooking Poole Quay

20. Designer Apartment inc. Free Parking & FAST WiFi

Find holiday rentals that suit your style

Top Osmington Hotel Reviews

Holiday Inn Express Poole by IHG

Sleeping Bear Hotel Dorchester

Sandbanks Hotel

Fairhaven Hotel

The Duchess of Cornwall Inn

The Knoll House

Haven Hotel

The Jubilee Hotel East- with Spa Facilities

Best Western Weymouth Hotel Rembrandt

Find out more about Osmington

Frequently asked questions

Go further with the Expedia app