A coastal town with colorful houses, a prominent hill in the background, and a clear blue sky.

Portland Holiday Rentals

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Our top choices for Portland holiday rentals

1. Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage in quiet location with room opening onto garden with lots of bird song. Snug with TV is very comfortable. Parking spot just outside cottage. Well appointed kitchen. Location is good for access to portland, but going elsewhere requires travelling through Weymouth which can be slow."
United Kingdom
Terry
The price is NZ$1,149
includes taxes & fees
3 Sept - 4 Sept
Mermaid Cottage

2. Lighthouse View

Lighthouse View
3.5 star property
Portland
6.0 out of 10, (1 review)
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
United Kingdom
Anonymous traveller
The price is NZ$658
includes taxes & fees
21 Aug - 22 Aug
Lighthouse View

3. Groves House

Groves House
3.0 star property
Portland
The price is NZ$1,090
includes taxes & fees
1 Sept - 2 Sept
Groves House

4. Home From Home

Home From Home
3.0 star property
Portland
The price is NZ$1,099
includes taxes & fees
26 Aug - 27 Aug
Home From Home

5. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is NZ$1,085
includes taxes & fees
19 Aug - 20 Aug
74 Reap Lane

6. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is NZ$1,652
includes taxes & fees
2 Sept - 3 Sept
Pebbles Reach

7. Coastguard View

Coastguard View
3.0 star property
Portland
The price is NZ$1,344
includes taxes & fees
17 Aug - 18 Aug
Coastguard View

8. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is NZ$1,319
includes taxes & fees
21 Aug - 22 Aug
Bear's Apartment

9. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is NZ$1,427
includes taxes & fees
12 Sept - 13 Sept
Manhattan Beach

10. Sea Gem

Sea Gem
3.5 star property
Portland
The price is NZ$2,227
includes taxes & fees
29 Aug - 30 Aug
Sea Gem

11. St Johns View

St Johns View
3.5 star property
Portland
The price is NZ$2,347
includes taxes & fees
29 Aug - 30 Aug
St Johns View

12. Kimberlin

Kimberlin
3.5 star property
Portland
The price is NZ$4,500
includes taxes & fees
4 Sept - 5 Sept
Kimberlin

13. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is NZ$2,840
includes taxes & fees
21 Aug - 22 Aug
The Old Portland Courthouse

14. Jurassic Coast House

Jurassic Coast House
3.5 star property
Portland
8.0 out of 10, Very good, (1 review)
"Nice size property. Missing the more luxury/comfort items. Garden furniture ok not as images. Has a comfy dining table. Balcony furniture present but not suitable for the area. High stools and table not appropriate needs more relaxing items to make area useful otherwise it was good for drying clothes. Area is central and easy for amenities, cafes, beach, shops etc all easy to walk to. Noisy as near heliport and some days this is busy from early morning till after 10 at night. Not overly...
United Kingdom
Michelle
The price is NZ$2,922
includes taxes & fees
29 Aug - 30 Aug
Jurassic Coast House

15. Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is NZ$1,053
includes taxes & fees
7 Sept - 8 Sept
Coastguard Lookout

16. Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!
Weymouth
8.4 out of 10, Very good, (5 reviews)
"Lovely property, well equipped and comfy beds"
United Kingdom
Kim E.
The price is NZ$330
includes taxes & fees
13 Sept - 14 Sept
Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

17. 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, (4 reviews)
"Responsive owner and lovely property"
United Kingdom
Benjamin
The price is NZ$777
includes taxes & fees
6 Sept - 7 Sept
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

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

Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage
Harman's Cross
The price is NZ$461
includes taxes & fees
16 Aug - 17 Aug
Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage

19. 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$383
includes taxes & fees
2 Sept - 3 Sept
Hardy View Farm House

20. Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage

Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage
Harman's Cross
The price is NZ$502
includes taxes & fees
17 Aug - 18 Aug
Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage
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 Portland Hotel Reviews

Find out more about Portland

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 Portland 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 Portland. 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 Portland. Seeing all the best attractions is bound to make you fall in love with Portland. 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 Portland short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Osprey Leisure Centre, or you can select a more secluded option if you're looking for a relaxing stay. Tourists appreciate the top-notch restaurants and bars in Portland. Make sure you have time to check out the university setting while you're in the area.

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

Beautiful, family friendly Cottage with sea views of Chesil Beach : This highly rated holiday home rental in Portland is located in a rural location, and has a fireplace, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Portland?

Choose from 20 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Cultural attractions include Portland Museum and Tout Quarry Sculpture Park, whereas Weymouth Bay and Dorset and East Devon Coast are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Portland Harbour and Portland Bill Lighthouse.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.