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

Holiday Rentals in Portland

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Our top choices for Portland holiday rentals

1. 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 €333
includes taxes & fees
3 Sept - 4 Sept
Lighthouse View

2. 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 €583
includes taxes & fees
3 Sept - 4 Sept
Mermaid Cottage

3. Groves House

Groves House
3.0 star property
Portland
The price is €552
includes taxes & fees
1 Sept - 2 Sept
Groves House

4. Home From Home

Home From Home
3.0 star property
Portland
The price is €557
includes taxes & fees
25 Aug - 26 Aug
Home From Home

5. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is €567
includes taxes & fees
13 Sept - 14 Sept
Anchor Cottage

6. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is €550
includes taxes & fees
19 Sept - 20 Sept
74 Reap Lane

7. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is €723
includes taxes & fees
12 Sept - 13 Sept
Manhattan Beach

8. Portland View

Portland View
2.0 star property
Portland
The price is €538
includes taxes & fees
13 Sept - 14 Sept
Portland View

9. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is €837
includes taxes & fees
2 Sept - 3 Sept
Pebbles Reach

10. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is €668
includes taxes & fees
20 Sept - 21 Sept
Bear's Apartment

11. The Shambles

The Shambles
3.5 star property
Portland
The price is €738
includes taxes & fees
13 Sept - 14 Sept
The Shambles

12. Coastguard View

Coastguard View
3.0 star property
Portland
The price is €681
includes taxes & fees
4 Sept - 5 Sept
Coastguard View

13. The View

The View
2.0 star property
Portland
The price is €937
includes taxes & fees
12 Sept - 13 Sept
The View

14. St Johns View

St Johns View
3.5 star property
Portland
The price is €1,189
includes taxes & fees
29 Aug - 30 Aug
St Johns View

15. Sea Gem

Sea Gem
3.5 star property
Portland
The price is €1,129
includes taxes & fees
29 Aug - 30 Aug
Sea Gem

16. 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 €1,204
includes taxes & fees
18 Sept - 19 Sept
Jurassic Coast House

17. Kimberlin

Kimberlin
3.5 star property
Portland
The price is €2,279
includes taxes & fees
4 Sept - 5 Sept
Kimberlin

18. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is €1,439
includes taxes & fees
29 Aug - 30 Aug
The Old Portland Courthouse

19. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
The price is €455
includes taxes & fees
31 Aug - 1 Sept
Chandlers Nook

20. Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is €533
includes taxes & fees
12 Sept - 13 Sept
Coastguard Lookout
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

Everything you need to know about Portland 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 Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland 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 Portland holiday rentals we have selected for you start as low as €169 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland 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 Portland 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 Portland 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 Portland. 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

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 19 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.