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Osmington Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Osmington vacation rentals

A stone cottage with a thatched roof, a wooden deck, and a round metal table with chairs and a small table set for tea.

1. Laurel Cottage

Laurel Cottage
3.5 star property
Weymouth
$554 nightly
The price is $665
Oct 9 - Oct 10
Total with taxes and fees
Laurel Cottage
A kitchen with a microwave, a coffee maker, and a window with a view of greenery.

2. Rose Cottage

Rose Cottage
2.0 star property
Weymouth
$805 nightly
The price is $966
Oct 8 - Oct 9
Total with taxes and fees
Rose Cottage
A bedroom with two single beds, a nightstand, a window, and a star-patterned rug.

3. Woodbine Cottage

Woodbine Cottage
2.0 star property
Weymouth
$758 nightly
The price is $910
Oct 12 - Oct 13
Total with taxes and fees
Woodbine Cottage
A cozy room with a stone wall, a fireplace, a sofa, and a window.

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
$647 nightly
The price is $777
Oct 31 - Nov 1
Total with taxes and fees
Norden Cottage
A room with large windows offering a view of a coastal landscape.

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
$1,016 nightly
The price is $1,219
Oct 12 - Oct 13
Total with taxes and fees
Waterson
A beach with people, a large striped tower, and buildings in the background.

6. The Sailors Studio|Sleeps2|Weymouth Beach|

The Sailors Studio|Sleeps2|Weymouth Beach|
Weymouth Town Center
$178 nightly
The price is $178
Oct 4 - Oct 5
Total with taxes and fees
The Sailors Studio|Sleeps2|Weymouth Beach|
A beach with a natural rock arch formation.

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
$359 nightly
The price is $359
Oct 11 - Oct 12
Total with taxes and fees
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
An outdoor deck with wooden tables and benches, string lights, and potted plants.

8. 39 Greenlands, Littlesea Holiday Park

39 Greenlands, Littlesea Holiday Park
5.0 star property
Weymouth
39 Greenlands, Littlesea Holiday Park
A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

9. 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
$171 nightly
The price is $171
Oct 6 - Oct 7
Total with taxes and fees
Cosy Peacehaven. Free on site Parking! Pet friendly!
A modern outdoor patio with wicker furniture and a glass door leading to a covered area.

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
$187 nightly
The price is $187
Nov 1 - Nov 2
Total with taxes and fees
Private Luxury By The Sea
A bathroom with a window, a sink, and two potted plants.

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.
$241 nightly
The price is $241
Oct 26 - Oct 27
Total with taxes and fees
Hardy View Farm House
A neatly made bed with two towels folded into robes, a pillow, and a small card on the bed.

12. 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
$191 nightly
The price is $191
Oct 8 - Oct 9
Total with taxes and fees
Glamping Cabin - Great for Hikers - Breakfast Inc!
A modern living room with a brick wall, a dining area with a table and chairs, and a sofa.

13. 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
$163 nightly
The price is $163
Oct 6 - Oct 7
Total with taxes and fees
Modern Apartment -Parking & WiFi
A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

14. 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
$208 nightly
The price is $208
Oct 10 - Oct 11
Total with taxes and fees
1 bedroom accommodation in Ibberton, Blandford Forum
A dining area with a round table, wicker chairs, and a view of boats at a marina.

15. 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.
$446 nightly
The price is $446
Oct 11 - Oct 12
Total with taxes and fees
Classic Yacht Nadine with Hot Tub, Poole Harbour Bay
A living room with a sofa, a coffee table, a bookshelf, and a mounted TV.

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.
$177 nightly
The price is $177
Oct 4 - Oct 5
Total with taxes and fees
Super Trendy Apartment - Free Parking & Fast WiFi
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.

17. 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.
$221 nightly
The price is $221
Oct 4 - Oct 5
Total with taxes and fees
Stylish modern retreat overlooking Poole Quay
A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

18. Sea Spray

Sea Spray
3.0 star property
Overcombe
$531 nightly
The price is $637
Oct 18 - Oct 19
Total with taxes and fees
Sea Spray
A bedroom with a large mirror, a bed, a chair, and a window with curtains.

19. Beautiful Couples Retreat - FREE Parking & WiFi

Beautiful Couples Retreat - FREE Parking & WiFi
Poole Old Town
10.0 out of 10, Exceptional, (5 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
$223 nightly
The price is $223
Oct 11 - Oct 12
Total with taxes and fees
Beautiful Couples Retreat - FREE Parking & WiFi
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

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.
Designer Apartment inc. Free Parking & FAST WiFi
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

Haven Hotel

Haven Hotel

8/10 Good
"Lovely location if you like to hear the waves at night. Good breakfast."
Patricia 3-night trip
Posted 7 hours ago
Haven Hotel

Find out more about Osmington

Everything you need to know about Osmington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osmington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osmington vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osmington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osmington rentals

At Expedia, we put the best Osmington vacation 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 vacation.

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 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.